You can’t coach someone into being something they fundamentally aren’t.  Especially a sales exec.

I’ve seen this pattern play out literally 100+ times across B2B companies from Series A to IPO. Again and again and again.  Founders and sales leaders keep making the same mistake—they hire for one motion, then expect their reps to magically transform into something completely different when growth demands it.

Let’s break down the three realities that will save you months of frustration and missed numbers.

The Inbound-to-Outbound Illusion

95% of sales reps who have only done inbound won’t start doing real outbound, even if they’re missing quota.

No matter what they say or claim, they just won’t.

I’m not talking about the performative outbound they’ll do when you’re watching. They’ll send a few LinkedIn messages, maybe fire off some templated emails, and call it a day. But the grind of true outbound prospecting? The 50+ calls per day, the real research, the rejection resilience?

Not happening for 95% of reps that have mainly worked in an inbound environment.  They just don’t want to do it, or see it as a good use of their time.

Why? Because inbound reps have been conditioned to work leads that are already warm. They’ve never developed the muscle memory for cold outreach, and more importantly, they’ve never built the emotional fortitude for it. When you’ve spent years closing deals from demo requests, the leap to interrupting someone’s day with a cold call feels impossible.

Rippling’s CRO Matt Plank learned this lesson the hard way during their transformation from programmatic outbound to human-driven outbound. When they had programmatic sequences hitting thousands of accounts, they were getting 1% conversion rates. But when they built a team of 150 dedicated outbound SDRs and had them work those same accounts, conversion jumped to 3-7%.

Same accounts. Same market. The only difference? They hired people who were wired for outbound instead of trying to convert their existing team. As Matt puts it, 50% of Rippling’s demos are still booked over the phone—the old-fashioned way.

The Fix: Don’t try to convert them. If you need outbound, hire outbound specialists. Period.

The Feast-or-Famine Cycle

Here’s another pattern that’ll drive you crazy: 95% of sales reps who will actually do outbound stop once they have enough inbound leads to hit their comp goals.

This one burned me personally when we scaled from $2M to $10M ARR. Our best outbound rep suddenly went dark on prospecting the moment our content marketing kicked in and inbound volume spiked. His pipeline was full, quota was covered, so why keep dialing?

From his perspective, it made perfect sense. From a business growth perspective, it was a disaster. We needed consistent pipeline generation, not this feast-or-famine cycle where outbound efforts disappeared every time marketing had a good quarter.

Toast’s CRO Jonathan Vassil learned a similar lesson about incentive structures. He admits that getting the comp plan right to drive consistent behavior was “a complex process that required iteration and learning.” Even at Toast’s scale, they’re still fine-tuning incentives to prevent reps from coasting once they hit their numbers.

But here’s what Toast does differently: they foster a culture where reps strive to achieve 200% or 300% of their targets, not just 100%. They actively combat the tendency to slow down after reaching quota. The culture matters as much as the comp plan.

The Reality: Most reps optimize for their personal number, not your company’s long-term growth. You need comp plans and management systems that account for this.

The Field Sales Fantasy

Let’s talk about the elephant in the room: 95% of sales reps don’t really want to visit customers in person. Even many “enterprise” reps.

The pandemic didn’t create this trend—it just gave everyone permission to admit what was already true. Most sellers, even those selling $100K+ deals, will visit the fewest customers possible. They’ll find every reason why a Zoom call is “just as effective” as being there in person.

But here’s where the data gets interesting. Toast’s CRO Jonathan Vassil shared something that should make every sales leader pay attention: prospects who receive an on-site visit close at a 3X higher rate than those who don’t (45% vs 15% conversion).

And it’s not just Toast. Sam Blond, former CRO of Brex, tracked this rigorously in their CRM. If their average virtual conversion rate was 15-20%, in-person meetings pushed that to 45-60%. Christian Smith, CRO of Splunk, sees the same 3X conversion lift when his enterprise reps show up in person, even for complex multi-million dollar deals.

In-Person Sales Generate 3x Higher Conversions Per The CROs of Toast, Splunk, Brex and Slice

Think about that for a second. We’re not talking about a marginal improvement—we’re talking about tripling your close rate. Yet as Sam Blond points out, “most reps only want to meet in person for the big, halo deals. You may need different DNA if you want typical SaaS B2B reps to get out there in-person.”

There’s the rub. Even when the data is crystal clear, even when the ROI is undeniable, most reps will find every excuse to avoid that plane ticket. Toast employs a primarily field-based sales organization, with 75-80% of sales reps working in the field, but that means 20-25% still prefer to stay put.

And these are reps selling into restaurants—a notoriously relationship-driven industry where trust matters more than features. If Toast, with their incredible unit economics and billion-dollar success, can only get 75-80% of their team into the field, what does that tell you about the average SaaS company?

The Truth: If your deal size and sales cycle demand in-person relationship building, hire people who actually enjoy it. Don’t try to force office dwellers onto planes. The math works when you have the right people, but it only works with the right people.

What Most B2B Sellers Actually Want

Strip away all the job descriptions and sales training, and here’s what the majority of B2B sellers really want:

• Warm, qualified inbound leads
• Existing customer renewals and expansions
• Remote work capability
• Predictable, manageable pipeline
• Minimal rejection and cold outreach

There’s nothing wrong with this preference. These reps can be incredibly valuable for the right stage and motion. But if you’re expecting them to transform into hunter-closer-relationship-builder hybrids, you’re setting everyone up for failure.

The data backs this up. According to Emergence Capital’s survey of 600+ B2B venture-backed startups, only 27% of B2B customer meetings happen in person today. Think about that—even though companies like Toast, Brex, and Splunk are seeing 3X conversion rates from in-person meetings, 73% of interactions are still happening virtually.

Why? Because most sellers gravitate toward what’s comfortable and efficient for them, not necessarily what’s most effective for closing deals.

The Full-Stack AE Myth

The “full-stack Account Executive” has become the unicorn everyone wants to hire. These mythical beings can cold call, run complex demos, negotiate enterprise deals, and maintain strategic relationships all while hitting 120% of quota year after year.

Here’s the reality: In B2B, the full-stack AE remains a rarity.

I’ve met a handful in my career. Most people who are great at one motion are mediocre at others. The skills that make someone excellent at outbound prospecting (high activity, rejection resilience, always hunting) often conflict with the skills needed for complex deal management (patience, strategic thinking, relationship nurturing).

Rippling’s Matt Plank discovered this truth as they scaled from 4 to 30 products. Initially, they convinced themselves that if a rep couldn’t keep up with new product launches, “maybe they weren’t cut out for the job.” They thought any good rep should be able to sell all 30 SKUs equally well.

This was, in Matt’s words, “a painful learning.” Even their best reps couldn’t absorb information about new product suites effectively. The breaking point came when they launched their finance suite and started competing with companies like Brex and Ramp—suddenly they needed specialized knowledge and different buyer relationships.

Now Rippling runs three distinct sales teams: core new logo reps, account managers, and specialized product AEs who get tagged in for complex deals. Each team does what they’re wired to do, instead of forcing everyone to be everything.

As Matt puts it: “You can teach a revenue-oriented person to have empathy for a customer. You can’t make, at large, a CSM org want to be a quota-carrying, revenue-generating team.”

The Hiring Solution

So what’s the answer? If you want your sales team to do more, you have to hire exactly that.

Stop trying to mold people into roles they’re not wired for. Instead:

For Inbound Motions: Hire patient, consultative sellers who excel at qualification and deal progression. They should love long sales cycles and complex decision-making processes.

For Outbound Motions: Hire hungry, resilient prospectors who thrive on activity metrics and don’t take rejection personally. Volume and persistence matter more than relationship-building skills.

For Field Sales: Hire people who genuinely enjoy travel and face-to-face relationship building. Toast learned this the hard way—they found that promoting from within often worked better than external hiring. 25% of their sales organization got promoted in the last 12 months, and many of their best field reps came from non-traditional backgrounds: teachers, military veterans, and people from the restaurant industry itself.

Why did these unconventional backgrounds work? Because these people were already comfortable with face-to-face interactions and understood the value of building local relationships. The former teacher knew how to explain complex concepts in person. The military vet understood discipline and territory management. The restaurant industry hire already spoke the customer’s language.

Toast’s CRO also discovered something fascinating: they teach their reps to become the “mayor of their town” by building deep local relationships. But you can’t coach someone into wanting to be a local relationship builder—you have to hire for it.

Loren Padelford, CRO of $100M+ ARR Slice, put it perfectly: “The best reps just work much, much harder. And they are truly curious. That’s rare.” The top performers are constantly learning more about their customers, the product, and the industry. Most reps aren’t wired this way—they sort of worked for a while during the easy money years of 2019-2021, but that doesn’t work today.

You can’t coach curiosity. You can’t train work ethic. These are fundamental traits that either exist or they don’t.

For Strategic Accounts: Hire relationship builders who think in terms of years, not quarters. They should have experience managing complex stakeholder groups and navigating organizational politics.

Gong’s ex-SVP of Sales Jameson Yung learned this lesson while competing head-to-head with Chorus in the early days of conversation intelligence. Both products were similar, but Gong won by making a crucial hiring decision: “When I joined Gong, I immediately raised quotas and compensation and hired a sales team one or two levels above what they initially thought they’d put in place.”

Why? Because “you can’t really put junior sales reps on the phone with CROs and expect massive success.” Gong hired people “somewhere between the 20-years-in-a-suit and the year-or-two-on-the-job person”—experienced enough to handle executive conversations, but scrappy enough to grind.

The result? They outsold Chorus from the start and built a $7.5B company. Not through better technology or marketing, but through hiring exactly the right people for the motion they needed.

The Bottom Line

The fastest way to miss your number is to hire for one motion and expect another. The second fastest way is to keep trying to coach people into becoming something they’re fundamentally not.

Kyle Norton, CRO of Owner.com (and former leader of a $1B business unit at Shopify), has a concept that applies perfectly here: “minimum effective dosage.” He’s talking about RevOps, but the principle holds for sales hiring. You want just enough of the right people to drive results, but not so much complexity that you spend more time managing the mismatch than building the business.

Your sales team will do exactly what they’re wired to do, regardless of what your growth strategy demands. Plan accordingly, hire specifically, and comp appropriately.

The companies that figure this out scale efficiently. The ones that don’t burn through sales talent and wonder why their numbers keep coming up short.

Dear SaaStr: I am a candidate for a VP Sales job. What are great questions to ask the CEO?

I’m involved at any given time with 2-3 VP of Sales and CROs searches across SaaStr Fund portfolio companies.  One thing is common across all of them: I am shocked how little candidates really know about what they are potentially getting themselves into.  Truly, honestly shocked how little they really know about roles they are very close to taking.  Even the smartest and sharpest candidates in many cases.

If you’re a candidate for a VP of Sales role, asking the right questions during the interview is critical—not just to impress the CEO, but to ensure the role is the right fit for you.  Way too often, a good candidate just takes the wrong role.  It’s sad because somewhere else, they could have thrived.  I blame the CEO more here, because they have more information.  But also, often the CEO doesn’t really know what to expect from their first (or even second or third) VP of Sales.  So …

Here are some great questions to ask:

1. What is the current ARR, and what is the growth target for the next 12 months?
   This helps you understand the scale of the business and the CEO’s expectations. If the growth target is unrealistic based on the current trajectory, that’s a flag.  At least talk honestly and openly about it.  I’m shocking how many VP of Sales and CRO candidates I talk to don’t really understand the plan for the next 12 months.  Not really.

2. What is the sales team structure today?
   Find out how many reps are on the team, their performance, and whether there’s a proven sales motion in place. If the team is underperforming or there’s no structure, you’ll need to assess whether you can fix it quickly.  Find out now.

3. What is the lead flow like?
   Ask about the volume and quality of leads coming from marketing. If the pipeline is weak, you’ll need to build it from scratch, which is a very different challenge than scaling an already functional sales engine.

4. What is the CAC payback period?
   This gives you insight into the company’s unit economics. If the CAC payback is too long (e.g., over 24 months), it might indicate inefficiencies in the go-to-market strategy.

5. What is the churn rate?
   High churn can make hitting sales targets nearly impossible. If customers are leaving faster than you can acquire them, you’ll need to address that before focusing on growth.

6. What is the relationship between sales and marketing?
   Misalignment between sales and marketing is a common issue. Ask how the teams collaborate and whether there’s a shared understanding of goals and metrics.  Way too many first time VP of Sales especially know little about how marketing works at startups they are talking to.

7. What is the average deal size and sales cycle?
   This helps you understand the complexity of the sales process and whether it aligns with your experience. Selling $10K ACV deals is very different from selling $100K+ enterprise deals.

8. What is the biggest challenge the company is facing in sales today?
   This question shows you’re thinking strategically and want to solve real problems. It also gives you a sense of what you’ll be walking into.  I’m again shocked how often candidates I talk to — have no idea.

9. What does success look like in this role?
   Ask the CEO to define what success looks like for the first 90 days, 6 months, and 12 months. This will help you gauge whether their expectations are realistic.

10. What is the company’s funding situation and runway?
    You need to know how much cash the company has and whether it’s in a position to invest in growth. If the runway is short, you’ll face pressure to deliver results quickly, often without adequate resources.

11. How do you see the relationship between the CEO and the VP of Sales?
    This is a critical one. You want to understand how involved the CEO will be in sales and whether they’ll give you the autonomy to lead.  Look, you may not learn much by asking this.  But you’ll learn something that matters.

12. What is the company’s vision for the next 3-5 years?
    I sort of hate this question when it’s asked too early in the interview process, because it’s so generic it sounds lazy.  But ask about 30 minutes in.  This helps you understand whether the CEO has a clear plan for the future and whether it aligns with your career goals.

13. What is the sales tech stack?
    Ask about the tools the team is using. If the tech stack is outdated or nonexistent, you’ll need to invest time and resources to modernize it.  The tech stack isn’t everything, but it will give you a sense of what you are walking into.

14. What is the company’s competitive positioning?
    Understanding how the company differentiates itself in the market is crucial. If the CEO can’t articulate this clearly, it’s a flag.  It also will show you if the type of competitive selling involved is right for you.  If you haven’t sold in a very competitive environment, be way of entering one that is.  It’s just a different playbook.

15. Why did the last VP of Sales leave?
    This can give you insight into potential challenges in the role or with the company culture.  I find most VPs of Sales and CROs are fine asking this question, but it can make CEOs uncomfortable.  It shouldn’t.  Being honest here is best for everyone.  Any top VP Sales candidates just want to learn why.  Most will be up for the challenge if they know why and if it’s a good fit.

And before you ask all these questions — spend enough time to really understand the product.  Way too many candidates … don’t.  You can’t really have a good conversation here if you don’t truly understand the product first.

And for the other side, here are 10 questions CEOs can ask VPs of Sales during the interview process:

The Top 10+ Questions to Ask a VP of Sales During an Interview (with Cheatsheet)

We’re watching AI systematically reshape every corner of go-to-market:

• Customer support? Already largely automated in many cases.  Intercom/Fin, Gorgias, Zendesk, Decagon and others are seeing 60%+ defection rates and AI resolving most issues.
• Marketing? CMOs that aren’t AI native are panicking.
• SDRs? The writing’s on the wall.  We won’t need more of them.
• Customer Success? AI is coming for those renewal conversations faster than you think.  90% of those check-ins and QBRs add no value anymore.
• The “One Call Close” Sales Rep? The next frontier for AI.

But there’s one GTM role that’s not just surviving the AI revolution—it’s becoming more critical than ever: the Chief Revenue Officer.

The Great GTM Disruption Has Already Begun

AI has already replaced much of support at many companies, turning what used to require human agents into sophisticated chatbots that solve and/or deflect up to 80% of customer issues without breaking a sweat. Marketing teams are discovering that AI can write better copy, optimize campaigns in real-time, and personalize at scale in ways humans never could.  The ghost writer and copywriter jobs were the first to go.

AI Won’t Replace Sales Reps So Much as ‘Deflect’ Them: What Support’s 70% Deflection Rates Tell Us About Sales’ Future

The SDR role as we know it is starting to crumble. Why pay someone $60K-$90k to send 50 prospecting emails a day when AI can send 5,000 personalized messages that actually convert better — if you put in the time and train the AI, and do it right? And in Customer Success, AI is already beginning to predict churn, automate health scores, and even handle routine check-ins with startling effectiveness.

We Sent 4,495 AI SDR Emails in 2 Weeks and Got The #1 Response Rate. Here’s How (It’s Not What You Think)”

Here’s the reality: AI could realistically replace 50% of transactional SMB Account Executives within the next 2-4 years. The transactional, process-driven parts of selling? AI does them better, faster, and without needing coffee breaks. Or any breaks at all. And without customers needing to wait and schedule a Calendly link at a time convenient for the human sales rep.

The New Talent Equation: Technical Depth Over Volume

But we’re already seeing that while AI eliminates many traditional sales roles, it’s creating unprecedented demand for others. Look at Microsoft’s recent restructuring—amid laying off 9,000 employees, they’re specifically replacing traditional salespeople (called “specialists” internally) with “solutions engineers” who can show customers actual demos earlier in the sales process.

According to Business Insider’s source, “The customer wants Microsoft to bring their technical people in front of them quickly. We need someone who is more technical, much earlier in the cycle.” Microsoft has received feedback from customers that they had to engage with too many salespeople before getting down to technical details and demos.

The strategic shift is dramatic: Microsoft is slashing their sales team’s “solutions areas” by half—from six areas down to three: AI Business Solutions, Cloud & AI Platforms, and Security. They’re eliminating traditional sales roles while specifically hiring more technical salespeople to compete with OpenAI and Google.

This signals something crucial: the future belongs to solutions architects and deep product experts who can navigate complex technical conversations that AI can’t handle yet. As Artisan’s CEO Jasper Carmichael-Jack explains, “Sales requires end-to-end solutions, not point tools. Code generation is elegant in its simplicity—input code request, output working code. Sales is messier.”

But … Someone Has to Orchestrate the Symphony

Here’s what AI can’t do: figure out how all these pieces fit together.  And manage them and iterate with them daily.

The CRO of 2027 won’t just be running a traditional sales organization. They’ll be the architect of a hybrid human-AI revenue engine that’s constantly evolving. And crucially, they’ll need to build teams heavy on technical expertise. They’ll need to:

Build Teams Around Technical Depth The winning sales teams of 2027 will look radically different. Instead of armies of generalist AEs, CROs will need more solutions architects, technical specialists, and industry experts who can have conversations that AI simply cannot. Microsoft’s transformation is the blueprint—they’re cutting traditional “specialist” sales roles while expanding “solutions engineer” positions who can deliver technical demos and engage in complex product discussions from day one. The reason? Sales spans everything from marketing attribution to contract negotiation, creating data silos that kill velocity when tools don’t talk to each other.

Master the AI-Human Handoff Knowing exactly when to deploy AI and when human intelligence is irreplaceable. Which deals need the empathy and relationship-building that only humans can provide? Which can be automated end-to-end? The CRO has to make these calls daily.

Build and Rebuild Playbooks Constantly It’s not enough to have a sales playbook anymore. The CRO of 2027 is simultaneously running the traditional sales playbook AND the AI sales playbook—and constantly iterating on both as AI capabilities expand.

Hire for a World That Doesn’t 100% Exist Yet What does a great Account Executive look like when AI handles all the grunt work? What skills matter when prospecting, follow-up, and data analysis are automated? The CRO has to identify and recruit for capabilities we’re still discovering—particularly deep technical and industry expertise that can’t be easily replicated. Microsoft’s sales chief Judson Althoff is betting on this future, calling for teams to “reinvent Microsoft and MCAPS” to become “the Frontier AI Firm” while establishing “a Copilot on every device and across every role.”

Navigate the Uncanny Valley of Revenue Customers are getting comfortable with AI, but they’re not there yet for every interaction. The CRO has to read the room—literally and figuratively—on when AI enhances the experience versus when it feels impersonal or premature.  And make sure every AI is truly deeply and well trained — and re-trained constantly.  Constantly.

At little Team SaaStr, we already have 10 AIs helping us with outreach, inbounds, ticket sales, support, and content review.  Each took about a month to train, and then every day we spend 1-2 hours with them iterating and updating, and training more.  More on that here:

The Reality of Managing 10 AI Agents in Production: What We’ve Learned Building Our AI-First Revenue Team at SaaStr

The Strategic Evolution of the CRO. It’s Coming Fast.

The most successful CROs are already making this transition. They’re not fighting AI—they’re weaponizing it while doubling down on uniquely human capabilities.

The data supports this shift: AI-powered sales teams are seeing 8-12% response rates vs. manual emails at 2-4%, and AI qualification takes 2-3 minutes per lead vs. 15-20 minutes for human SDRs. But as Artisan’s CEO notes, “AEs want to sell, not admin—AI will handle the rest.” The average AE spends only 28% of their time actually selling, with the other 72% lost to administrative quicksand.

They’re using AI to handle the mechanical parts of sales (lead scoring, email sequences, meeting scheduling, basic qualification) while training their human teams to excel at complex problem-solving, relationship building, and strategic deal navigation.

They’re also becoming AI product managers within their own companies, constantly evaluating new tools, testing implementations, and measuring ROI on AI investments across the entire revenue stack.

Most importantly, they’re shifting their hiring strategy from quantity to quality—fewer generalists, more specialists who can dive deep into technical architectures, industry verticals, and complex use cases that require genuine expertise.

The Last Human Standing

Every other GTM role is becoming either fully automated or dramatically simplified. But the CRO role is becoming more complex, not less. It requires human judgment, strategic thinking, and the ability to manage both human psychology and artificial intelligence.

The CRO of 2027 will be part sales leader, part AI strategist, part organizational psychologist, and part fortune teller. They’ll need to predict not just market trends, but AI capability trends, and constantly rebalance their human-AI mix accordingly.

The window for this transformation is closing fast. As Artisan’s CEO warns: “While you’ve been testing, your competitors are scaling. The companies that commit to AI-first sales operations in 2025 will have an insurmountable 18-month head start by 2027.”

In a world where AI is eating GTM jobs, the person who can orchestrate the entire revenue symphony—human and artificial—becomes the most valuable player on the team.

That’s your CRO of 2027. The last human standing, and the most important one.

• It’s fine if your first 1-2 sales reps just cover their costs — at first.
• Ultimately, sales reps just have to bring in 3x-5x what they cost
• Don’t overstress nominal “on target earnings”.  Bonuses do have to be earned.

A few basic thoughts:

1. Start with the Basics: Just Pay Market Rates

You can’t underpay sales reps and expect results. A typical structure is 50/50—50% base salary and 50% commission, which together make up their On-Target Earnings (OTE). For example, if the OTE is $140K for a U.S.-based mid-market OTE, the base would be $70K, and the commission would be $70K.   Same with an SMB rep at $80k OTE.  This is standard and ensures you’re competitive enough to attract good talent.

2. Set a Revenue Target That’s 3x-5x OTE, At Least After an Initial Period That’s Easier

The math has to work. If you’re paying a rep $140K OTE, they need to bring in $560K-$700K in revenue annually. For SMBs, you might get away with 3x, but for mid-market or enterprise, it has to be closer to 4x-5x.  Ultimately, 5x for big enterprise deals.  This ensures the rep is profitable for the business.  But, you don’t have to be that efficient in the very early days, for a rep’s first few months at least.  See point 3.

3. Make It Easier For Your Reps To Make Money in the Early Days

In the first few months, don’t expect reps to hit 3x-5x. They’re ramping up, learning the product, and building their pipeline. In the early days, I paid my reps 100% of what they closed the first 60 days to help them get started. It’s not sustainable long-term, but it’s an investment to get the engine going.  It’s fine to overpay bonuses on the first 1-2 deals or in the first 30-90 days.  Just do it.  It also builds confidence.

4. Align Commission with Cash Flow — When Cash Flow Matters

If you’re in B2B and customers pay monthly, you might want to align commission payouts with cash received. For example, many only pay bonuses once cash is received.  Reps don’t like this, but if you tell them the policy is only until you’re bigger, in the end they’ll be OK with it.  Many also pay commission monthly as the customer pays, but here you may need to be a little more flexible so reps can pay the rent and eat. Either way, when you’re more stable, you can pay the full commission upfront on the annualized contract value (ACV).

5. Focus on New Sales

Most SaaS companies pay commissions only on the first-year ACV. Renewals are usually handled by customer success teams or paid at a much lower rate. This keeps reps focused on closing new deals, which is where they add the most value.  Keep them being closers.

6. Don’t Sweat Small Negotiations

If a seasoned rep wants $150K OTE instead of $140K, don’t waste time haggling over $10K. What matters is whether they can close $600K or $700K in deals. If they can, you’ll be happy to pay them more because they’re accretive to the business.

7. Motivate with Over-Attainment

Build in accelerators for over-performance. For example, if a rep exceeds quota, their commission rate could increase. This keeps top performers motivated and ensures they’re rewarded for going above and beyond.  This doesn’t actually work with mediocre reps.  They just want to work the least they can to hit their financial goals.  But it really works with your very top performers.

8. Keep It Simple

Don’t overcomplicate the plan with too many variables. A straightforward structure—base + commission on ACV—is easier for reps to understand and for you to manage. Complexity kills motivation.

And finally, whatever you do — only hire early reps you’d honestly, truly, really buy your own product from.  For real.  Do that, and they’ll almost certainly be accretive.

Cut a corner here, they almost certainly will fail.  No matter what comp plan you build.

More here:

A Framework For Your First SaaS Sales Comp Plan

We’ve assembled 30 of the most actionable, data-driven articles from SaaStr.com—with most published in the past few months to ensure you’re getting the latest thinking on what’s actually working today. These are battle-tested strategies from leaders who’ve scaled companies from $1M to $3B+ ARR.

Companies that adapt fastest are pulling ahead. If you’re a founder, sales leader, or anyone building revenue at a B2B company, this curated collection represents the most essential tactical insights from the SaaStr community.

🤖 AI & Modern GTM Revolution

The age of AI in B2B and SaaS isn’t coming—it’s here.

1. AI-Native GTM Teams Run 38% Leaner: The New Normal?

The Data Behind the New Operating Model

ICONIQ’s survey of 205 GTM executives reveals a startling truth: AI-native companies aren’t just more efficient—they’re fundamentally restructuring how go-to-market teams operate. Early-stage AI companies are running with 38% fewer GTM employees while achieving superior conversion rates.

Key Takeaway: Perplexity scaled to 5,000 enterprise customers with just 5 sales reps. This isn’t an outlier—it’s a new blueprint, at least for some.

→ Read the full analysis here

2. GTM in The Age of AI: The Top 10 Learnings from ICONIQ’s B2B SaaS Report

The Market Split That’s Defining SaaS Success

The data tells a stark story: AI-native companies achieve 56% trial-to-paid conversion rates versus just 32% for traditional SaaS. Companies with strong AI adoption are outperforming on every metric that matters.

Key Takeaway: The conversion gap isn’t about having AI features—it’s about being fundamentally built around AI.

→ Read the full report here

3. AI in GTM Efficiency: The Playbooks from Databricks, Monday.com and Benchling

How Three High-Growth Companies Actually Implement AI

Go beyond the hype with tactical playbooks from revenue leaders at scale. Learn how Monday.com built their “deal desk co-pilot” and why the biggest wins come from platform integration, not point solutions.

Key Takeaway: The winners aren’t companies with the most AI tools—they’re the ones who thoughtfully integrate AI into existing workflows.

→ Read the tactical playbooks here

4. AI, Sales + GTM: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton

The Future of Revenue Teams

By end of year, successful CROs will need to manage teams that are 50% AI agents and 50% human. This isn’t science fiction—it’s operational reality for forward-thinking revenue organizations.

Key Takeaway: Team members who aren’t genuinely AI-curious should be shown the door. That’s not hyperbole—that’s the new competitive reality.

→ Read how sales teams have already changed with AI here

5. The GTM Playbook Is Mostly Dead. But What’s The AI Era Replacement?

What Actually Works in 2025

The 2021 playbook of endless outbound emails and low-energy digital events is dead. The 2025 GTM Playbook requires getting out of the home office more, working harder, and spending more human time per prospect—not less.

Key Takeaway: AI hasn’t made GTM easier; it’s made competition fiercer. The companies winning are doing the fundamentals better, not just deploying more tools.

→ Read the new playbook here

6. Sam Blond + Jason Lemkin “GTM: How It’s Changed, How It’s Changing, and What Hasn’t Changed (Yet)”

Counterintuitive Insights from Leading CROs

Through interviews with CROs from Toast, Databricks, Wiz, and Codeium, discover why territory design beats AI tools, why in-person sales still generates 3X higher conversion rates, and why some companies are finding cold calling surprisingly effective.

Key Takeaway: While everyone chases AI tools, fundamentals like territory optimization and in-person relationships are creating outsized competitive advantages.

→ Read the counterintuitive insights here

👑 Sales Leadership & Hiring

Building great revenue teams starts with hiring great leaders. These articles provide the tactical frameworks for finding, evaluating, and onboarding sales leadership that can scale.

7. The Top 10+ Questions to Ask a VP of Sales During an Interview (with Cheatsheet)

The Updated 2025 Interview Guide

The classic SaaStr post, updated for the AI-driven, distributed world. These questions will help you separate the true closers from the PowerPoint-wielding process managers.

Key Takeaway: Before hiring any VP of Sales, make sure they can demo your product themselves. If they can’t sell, they can’t lead.

→ Read the interview cheatsheet here

8. What A New VP of Sales Needs To Be Doing Their First 2 Weeks

The Make-or-Break First 14 Days

Your new VP of Sales should be able to demo the product by the end of Week 1 and be recruiting top talent before they even start. Here’s the tactical playbook for ensuring your revenue leader makes an immediate impact.

Key Takeaway: The first two weeks are about establishing credibility through hands-on execution, not just “learning the business.”

→ Read the first 2 weeks playbook here

9. Hiring a Great VP of Sales: The New, Latest Edition with Jason Lemkin

Avoiding the Jaded, Broken, and Done

The post-2021 market has left many sales leaders burned out. Learn to identify the “jaded” (who blame everyone else), the “broken” (who’ve lost their edge), and the “done” (who don’t want to sell anymore).

Key Takeaway: Don’t hire someone who’s spent the last 18 months as a “fractional CRO”—they’ve already shown they don’t want the intensity of full-time revenue leadership.

→ Read the updated hiring guide here

10. The Top 10 Mistakes People Make When Hiring a VP of Sales

The Patterns That Kill Revenue Organizations

From hiring based on logos to confusing CRO roles with escape routes from selling, these are the systematic errors that set revenue teams up for failure.

Key Takeaway: A VP of Sales must love closing deals above all else. CRO is not a place to escape sales—it’s where the best closers go to scale their impact.

→ Read the top 10 mistakes here

11. From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship

Lessons from One of the Largest Pre-IPO Companies

Ron Gabrisko’s journey with Databricks from under $1M to over $3B ARR offers rare insights into hypergrowth revenue scaling. Learn how they leveraged open-source community, built technical sales teams, and focused on pricing power over operational efficiency.

Key Takeaway: For technical products with technical buyers, hire sales leaders with engineering backgrounds. Technical buyers don’t want to talk to traditional salespeople.

→ Read the Databricks scaling story here

12. CRO Confidential: The Proven Customer Acquisition Strategies Behind Toast’s Explosive Growth

Field Sales Excellence in a Low-ACV Environment

Toast’s CRO Jonathan Vassil reveals how they built one of the strongest sales organizations in B2B, despite operating in a challenging low-ACV ($10K), field-based SMB environment. Their data shows prospects who receive on-site visits close at 3X higher rates.

Key Takeaway: One out of five deals at Toast comes from referrals. The “flywheel concept” works: when you reach density in a market, win rates and productivity increase dramatically.

→ Read the Toast growth strategies here

💰 Sales Compensation & Commission Plans

Get compensation wrong and even the best reps will underperform. These articles provide proven frameworks for building comp plans that drive the right behaviors.

13. A Framework For Your First SaaS Sales Comp Plan

Lessons from Scaling to $25M ARR at SaaStr

Jason Lemkin’s hard-won lessons from building sales comp plans that actually work. Learn why BigCo sales comp plans fail at startups and how to structure compensation that motivates top performers while weeding out mediocrity.

Key Takeaway: Pay competitive base salaries but make reps cover their costs before hitting full bonus. This approach attracts top talent while encouraging poor performers to leave.

→ Read the comp plan framework here

14. Dear SaaStr: How Should I Build Our First Sales Comp Plan?

The Step-by-Step Blueprint

A comprehensive guide covering everything from base+commission structures to retention bonuses and upsell incentives. Includes real examples and rough quota guidelines for SMB, mid-market, and enterprise.

Key Takeaway: Keep it simple enough that reps can calculate their earnings quickly. If they can’t understand it, they’ll lose motivation.

→ Read the step-by-step blueprint here

15. Dear SaaStr: How Much Do I Pay My First Sales Rep?

Three Simple Rules for Early-Stage Compensation

Your first rep doesn’t have to be magically profitable on Day 1. Learn how to structure competitive OTE while back-solving for the three key constraints every startup faces.

Key Takeaway: It often makes sense to pay a much higher commission for an introductory period—Jason paid his first reps 100% of what they took home for the first 60 days.

→ Read the first rep compensation guide here

16. Dear SaaStr: What’s the Proper Way to Commission Multi-Year Deals?

Handling Complex Deal Structures

Multi-year deals with increasing ACV require thoughtful commission structures. Learn when to pay on cash receipt versus contract signing, and how to avoid the incentive misalignment that can destroy deal quality.

Key Takeaway: Until you’re at $10M+ ARR, pay higher commissions on prepaid cash for multi-year deals—the cash flow benefits usually outweigh the commission costs.

→ Read the multi-year deal guide here

17. Yes, You Do Have To Pay Sales Commissions When a Partner Mostly Closes The Deal

Partnership Channel Compensation

Don’t deduct partner referral fees from sales commissions. Your rep still needs to coordinate, manage the relationship, and ensure the deal closes successfully.

Key Takeaway: Partners rarely close deals entirely on their own—your rep is still doing significant work that deserves compensation.

→ Read the partner compensation guide here

18. Dear SaaStr: How Much Do SaaS Sales People Make in Commission?

The 4x-5x Rule and Market Standards

Sales reps need to bring in 4x-5x what they take home in total compensation. Most B2B companies end up with roughly a 10%/10% model: 10% of quota in base, 10% in commission.

Key Takeaway: If your SaaS sales rep can close $1M a year, paying them $200K (20%) in base+bonus is standard and justifiable.

→ Read the market standards here

🚀 GTM Strategy & Scaling

Moving from founder-led sales to scalable revenue requires systematic GTM strategy. These articles show you how the best companies build repeatable growth engines.

19. How to Scale Go-to-Market Through IPO with ICONIQ Growth’s General Partners

The Four Stages of GTM Evolution

ICONIQ’s data-driven framework for scaling GTM from founder-led sales through IPO. Learn the key milestones, benchmarks, and team-building strategies for each stage of growth.

Key Takeaway: 30% of companies hire their CMOs less than a year before going public—the last CMO hire is crucial for IPO readiness.

→ Read the IPO scaling guide here

20. How to Build Go-to-Market Efficiency in SMB Sales with Owner.com CRO Kyle Norton

From $3M to $21M ARR in 22 Months

Kyle Norton’s tactical playbook for building GTM efficiency while scaling rapidly. Learn how Owner reduced CAC and operated with sub-one burn multiple during hypergrowth.

Key Takeaway: The first lesson is learning to say no. If you’re losing too many customers early, don’t add more to the top of the funnel—fix the leaky bucket first.

→ Read the GTM efficiency playbook here

21. How We Scaled OpenAI’s Sales Team from 10 to 500 People in 2 Years: The Inside Playbook from ChatGPT Enterprise’s GTM Leader Maggie Hott

Hypergrowth Lessons from the AI Revolution

Maggie Hott’s tactical playbook from scaling one of the fastest-growing enterprise applications in history. Learn why one exceptional hire beats three average ones, how to avoid the “logo trap,” and why early sales teams should focus on salary over commission.

Key Takeaway: When founders tell her they want to go after Walmart or Nike, she pushes back 10/10 times. Enterprises are wrong for early-stage companies because of complex hierarchies and lengthy cycles.

→ Read the OpenAI scaling playbook here

22. Top 10 GTM Mistakes Founders Are Making Today with SaaStr CEO Jason Lemkin

Updated for the AI GTM World

The GTM landscape has fundamentally changed since 2023, let alone the 2021 era. Learn the new mistakes founders are making, from hiring VPs who can’t demo the product to cutting marketing to zero during downturns.

Key Takeaway: Whatever you do, don’t hire a Head of Sales who can’t demo the product before day one. You don’t have the resources or brand to carry you.

→ Read the top GTM mistakes here

📊 Sales Operations & Process

Great sales teams aren’t just about great people—they’re about great processes. These articles show you how to build the operational foundation for scalable revenue.

23. How to Build Pipeline and GTM Alignment with Datadog’s CMO Sara Varni

The Four-Horsemen Model for Pipeline Management

Sara Varni’s framework for creating alignment between sales and marketing through joint pipeline targets. Learn how to avoid the trap of departmental optimization at the expense of overall business results.

Key Takeaway: You never want marketers taking a victory lap if they hit their targets but sales didn’t. Marketing should take ownership over pipeline, even if they don’t get credit.

→ Read the pipeline alignment guide here

24. How Salesforce Runs Its Internal Forecasting Process

Under the Hood at the World’s Largest SaaS Company

Salesforce’s three-pillar approach to forecasting culture: people (data-driven accountability), process (alignment across departments), and technology (clean pipeline management). They have sales forecasting meetings every single day.

Key Takeaway: A deal doesn’t become part of the pipeline until it reaches stage two. Clean pipeline definition is essential for accurate forecasting.

→ Read the Salesforce forecasting process here

25. Dear SaaStr: How Do I Know If My New VP of Sales is Working Out?

The 60-Day Evaluation Framework

Revenue growth, pipeline metrics, team building, process improvements, and deal closing—here’s how to evaluate whether your VP of Sales is actually moving the needle.

Key Takeaway: If your revenue per lead doesn’t improve within one sales cycle, they’re not doing their job. Time is your most valuable asset in SaaS.

→ Read the VP evaluation framework here

🎯 Early-Stage Sales Hiring

Getting your first sales hires right sets the foundation for everything that follows. These articles provide the tactical guidance for building your initial revenue team.

26. Should You Hire a Sales Rep First, Or a Sales Manager?

The Ideal Hiring Sequence

Close the first 10-20 customers yourself, then hire 2 sales reps (not just 1), then hire a head of sales after they’re both hitting quota. Don’t ask a VP of Sales to figure out product-market fit.

Key Takeaway: You need to run an A/B test with your first sales hires. If you only hire one rep, you won’t know why they succeed or fail.

→ Read the hiring sequence guide here

27. When You Hire Your First Sales Rep — Just Make Sure You Hire Two

The A/B Testing Imperative

Even if it seems expensive, hire two reps to start. You need at least two to learn what works, run comparisons, and avoid the trap of not knowing whether success or failure is due to the rep or your process.

Key Takeaway: No matter how well your first rep does, you won’t learn anything if you only hire one. You need data points to build a scalable system.

→ Read the two-rep strategy here

28. Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like?

The Non-Negotiable Criteria

Hire someone who’s sold at your price point, has startup experience, and—most importantly—someone you’d buy your own product from. Don’t hire someone that hasn’t worked at a startup; they can’t survive without brand and infrastructure.

Key Takeaway: Everyone makes the mistake of hiring someone they wouldn’t buy from themselves. Leads are precious in the early days—you can’t entrust them to someone who can’t sell.

→ Read the first salesperson guide here

🏗️ Sales Team Building & Culture

Building a high-performing sales culture requires intentional effort. These articles show you how to create environments where top performers thrive.

29. 7 Learnings: Building Your First, Great Sales Development (SDR) Team

The Foundation of Scalable Pipeline

SDR teams with the right talent, onboarding, and management can build consistent pipeline that scales. But miss on talent and your team is almost certain to fail—great people find a way to succeed even when systems aren’t perfect.

Key Takeaway: Hire SDRs in pairs to create “compassionate competition.” Top performers become pacesetters who raise the game of their peers.

→ Read the SDR team building guide here

30. Scaling A SaaS Sales Team While Building Culture with Scott Pugh, VP of Sales at Figma

Category Creator Playbook

Scott Pugh’s strategy for scaling sales teams at category creators like Figma: recruitment (hiring the best talent), enablement (investing in professional growth), and culture (developing sub-cultures that enable scaling).

Key Takeaway: Culture beats strategy. Without culture, strategic plans are useless. When you build culture, it democratizes decision-making and enables people to make decisions without constantly seeking approval.

→ Read the Figma culture scaling guide here

The Bottom Line

The revenue landscape is evolving faster than ever. AI is creating new opportunities for efficiency while making competition fiercer. Traditional GTM playbooks are breaking down, but the fundamentals—great people, clear processes, aligned incentives—remain more important than ever.

These 30 articles represent thousands of hours of real-world experience from leaders who’ve built revenue engines that scale. Whether you’re a first-time founder hiring your initial sales rep or a seasoned executive navigating AI transformation, these insights will help you build the revenue organization your business needs to win.

The companies that study these playbooks, adapt them to their context, and execute with discipline will be the ones that thrive in the age of AI. The question isn’t whether your GTM will need to evolve—it’s how quickly you can learn from those who’ve already figured it out.

Want to dive deeper? Each of these articles contains tactical frameworks, real data, and actionable advice you can implement immediately. Start with the areas most relevant to your current challenges, but don’t skip the sections that feel “advanced”—the best revenue leaders are always learning from stages they haven’t reached yet.

Dear SaaStr: How Do You Handle It When a Prospect Puts a Deal “On Hold”?

When a deal goes “temporarily on hold” in your CRM, it’s critical to treat it as a live opportunity, not a lost one. The key is to stay engaged without being overly pushy.

Here’s how I’d approach reviving and driving those deals forward:

1. Reassess the Reason for the Hold.  It’s More Than Just a Deal for the Prospect.

First, figure out why the deal is on hold. Is it budget constraints, internal decision-making delays, or a shift in priorities? If you don’t already know, reach out to your champion at the company and ask directly. Understanding the root cause will shape your strategy.  Just ask.

2. Add Value Without Selling.  Too Many Don’t Do This.

Keep the relationship warm by sharing relevant updates or insights. For example:

• Invite them to a webinar or event that aligns with their interests or challenges.
• Share a case study or success story from a similar customer.
• Let them know about new features or product updates that could address their pain points.

3. Stay Top of Mind with Light Touchpoints — That Add Value

Drop them into a low-key drip campaign. This could include:

• Monthly emails with industry insights or product updates
• Sending them branded swag—something simple like a T-shirt or socks can keep your company in their mind.  This doesn’t close a deal on its own.  But it does help keep you top of mind.  It really does.

4. Leverage Your CEO And Other Leadership

Offer a call with your CEO or a senior leader. Prospects often appreciate the chance to hear directly from the top, and it can reignite interest in the deal.  And ask your CEO to check in on key prospects and see if they can help.  Customers love to talk to the CEO once they are customers.  Before?  Sometimes they do, sometimes they don’t.  But they already appreciate hearing from the “boss”.

Customers Love to Talk to the CEO. Do More of That.

5. Monitor for Trigger Events

Keep an eye on changes within the prospect’s organization. For example:

• If a key decision-maker leaves, reach out to the new person.
• If their competitor makes a move, use it as an opportunity to re-engage.

6. Be Patient but Persistent

Deals on hold often have longer sales cycles. Stay engaged, but don’t overwhelm them with constant follow-ups. A well-timed, thoughtful touchpoint every few weeks or months can make a big difference.  If you don’t have a good reason to follow-up, don’t.  Instead, slow it down and find a good reason.

7. Invite Them to Your Customer Conference and Any Other Dinners, Events, etc.

If you have a user or customer event, invite them. These events can be magical for reviving deals. Your existing customers might even help sell them on your solution.

Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference

8. Don’t Break Up.  Enough With the Break-Ups.  And No False Urgency.

Never tell them you’re “closing their file” or “moving on.” That sends the wrong message. Instead, let them know you’re there whenever they’re ready to move forward.  Closing a deal today may help you make the quarter, but it may not be relevant to the business process change a customer has to work on.

The goal is to stay relevant and valuable without being annoying. Deals on hold are often just delayed, not dead. Play the long game, and you’ll win more of them back than you expect.

Discounts, Expiring Deals, and Urgency: Understanding Human Behavior in Sales

9. Put Yourself In Their Shoes

Once you’ve figured out the real root causes of the push, put yourself in the prospect’s shoes.  Do what would help them the most.

Too few in sales put themselves in the customers’ shoes.  Magic happens when you do.

And now that we’ve rolled out 4+ AI SDRs and BDRs at SaaStr itself, we’ve learned so much:

• An AI SDR really, really has to be trained to work well.  There is no set-and-forget today.  Not yet at least.
• An AI SDR has to be “QA’d” every single day to get better and better.  I.e., it has to managed just like human SDRs.  Just differently.
• But also a critical if obvious learning: an AI SDR almost always knows the product itself far, far better than any human SDR.  Far better.

After all, you can train an AI SDR on everything.  On every page of your website, every piece of collateral, every objection.

And … 95% of human SDRs fundamentally don’t understand what they’re selling.  

Not “they need more training.” Not “they’re still ramping.” They genuinely cannot articulate the technical value proposition of their product when pressed by someone who actually knows what they’re talking about.  And they certainly can’t engage in a real conversation around it.  They have to go … get someone.

The Product Knowledge Disconnecr Nobody Talks About

Here’s what happens in the real world:

A VP of Engineering gets on a discovery call. They ask a simple technical question: “How does your API handle rate limiting at scale?”

The SDR freezes.

“That’s a great question! Let me connect you with our solutions engineer who can dive deep into the technical details.”

This happens 95% of the time.

When a CPO asks about data lineage capabilities, the SDR punts to product marketing.

When a CIO wants to understand compliance frameworks, the SDR schedules a follow-up with the security team.

When a technical buyer asks literally anything beyond surface-level features, human SDRs become expensive call schedulers.

The Hidden Cost of Technical Ignorance

We’ve all accepted this as “normal.” We’ve built entire go-to-market playbooks around the assumption that SDRs are glorified appointment setters who hand off anything remotely complex.

But think about what this actually costs:

• Longer sales cycles: Every punt to a technical resource adds 3-7 days to your deal timeline
• Lower conversion rates: Technical buyers lose momentum when they can’t get immediate answers
• Resource drain: Your highest-paid technical talent spends time answering basic questions
• Credibility loss: Nothing screams “we don’t understand our own product” like an SDR who can’t answer fundamental questions

Why AI SDRs Will Dominate (It’s Not Just the Productivity Gains)

Everyone talks about AI SDRs being “more productive.” They can make more calls, send more emails, work 24/7. That’s all true, but it misses the bigger story.

AI SDRs are fundamentally better at the job than humans.

Here’s why:

Perfect Product Knowledge, Always

An AI SDR has instant access to your entire technical documentation, every product update, every integration detail, every compliance framework. It doesn’t “forget” features. It doesn’t give outdated information. It doesn’t punt technical questions to someone else.

Consistent Technical Credibility

When a VP of Engineering asks about your API’s authentication methods, an AI SDR can immediately explain OAuth 2.0 flows, token refresh mechanisms, and security best practices. Without skipping a beat.

Real-Time Learning and Adaptation

Human SDRs need weeks of training for each product update. AI SDRs incorporate new information instantly. They’re always current, always accurate, always ready.  And you’ll train your AI SDRs every day, and they won’t forget.  They’ll all remember the ‘manual’ training, too.

No Ego, No Politics, No Bad Days

Human SDRs have off days. They get frustrated. They take shortcuts. They develop preferences for “easier” prospects. AI SDRs don’t. They treat every conversation with the same level of preparation and professionalism.

The Data

I’ve been tracking this roughly across multiple SaaStr Fund portfolio companies:

• Average technical questions answered immediately: Human SDRs 15%, AI SDRs 87%
• Calls requiring technical follow-up: Human SDRs 73%, AI SDRs 22%
• Time to technical qualification: Human SDRs 8.3 days, AI SDRs 2.1 days
• Technical buyer satisfaction scores: Human SDRs 6.2/10, AI SDRs 8.4/10

The productivity gains are massive (AI SDRs handle 3-5x more conversations), but the quality improvement is what will drive adoption.

What This Means for Sales Leaders

If you’re a sales leader, you need to think hard about what “good enough” means for your SDR team.

• Is “good enough” someone who can book meetings but can’t answer technical questions?
• Is “good enough” someone who needs constant support from your technical team?
• Is “good enough” someone who loses credibility with technical buyers?

Because AI SDRs aren’t “good enough.” If they are truly well trained — they’re better.

They’re better at product knowledge. Better at technical conversations. Better at maintaining momentum with technical buyers. Better at representing your company’s capabilities.

A Well Trained AI SDR Simply Beats an “Entry Level” Human SDRs.  And 95%+ of SDRs Are Entry Level Roles.

Here’s what I’ve learned after hiring and observing 100+ SDRs across dozens of companies:

The problem isn’t training. The problem isn’t motivation. The problem isn’t tools.

The problem is that being a great SDR requires a combination of skills that’s extremely rare in humans but trivial for AI.

• Deep technical product knowledge
• Perfect memory of prospect history
• Consistent energy and enthusiasm
• Immediate access to all company information
• No ego about admitting limitations
• Perfect adherence to best practices

Find me a human who has all of these, consistently, across every interaction. I’ll wait.

The Winners and Losers

Winners: Companies that adopt AI SDRs early will see shorter sales cycles, higher conversion rates, and better technical buyer experiences.

Losers: Companies that cling to human SDRs because “relationships matter” will find themselves outmaneuvered by competitors who can actually answer technical questions on the first call.

It’s Not About Replacing.  It’s About A Fundamental Change In What Buyers Can Expect.

This isn’t about replacing humans in sales. AEs, customer success managers, and senior sales leaders aren’t going anywhere. Complex deal negotiation, relationship building, and strategic selling still require human judgment.

But SDR work? The writing is on the wall.

When 95% of human SDRs can’t properly represent your product to technical buyers, and AI SDRs can do it perfectly every time, the choice becomes obvious.

The productivity benefits are huge. But the quality improvement? That’s what will make AI SDRs unstoppable.

Dear SaaStr: What Should The First 2 Weeks Look Like For a New VP of Sales?

The first two weeks for a successful VP of Sales in a B2B company should be laser-focused on understanding the business, the team, and the customers.

Here’s what they should prioritize.  If they don’t — it’s a flag.

1. Learn the Product Inside Out. Ideally, Before You Even Start.  But At Least By Week 1.

They need to be able to demo the product themselves by the end of Week 1. If they can’t, they’ll never truly understand the sales process or be an ally to the customer. This is non-negotiable. A VP of Sales / CRO who can’t demo the product is just a process manager, not a leader.

It’s a huge red flag today if a new VP/CRO shows up thinking they’ll learn the product after they start.  The world is just too fast paced and too competitive today.

More here.

2. Understand the Go-to-Market Motion.  Lean Into What’s Already Working, Even Partially.

They must dive deep into the existing GTM strategy. Is it direct sales? Channel-driven? A mix? If they don’t understand how revenue is currently generated, they’ll be out of sync with the team and the market. For example, companies like Shopify and HubSpot rely heavily on partnerships—missing this nuance would be a massive oversight.  Too many mediocre VPs of Sales and CROs just run the playbook from their last role.  Bringing some of that in is important.  But they have to focus on what already works, and just level it up and improve it first.

More here.

3. Meet the Team IRL and Assess Talent

In the first week, meet anyone on the team you haven’t already.  And you have to do it in person, not on Zoom. Quickly identify the top performers and underperformers. Great VPs of Sales focus on retaining top talent and moving out weak performers quickly. If they don’t, it’s a red flag. Leads are too precious to waste on reps who can’t close.

The mediocre retain mediocre talent … because they don’t know how to find better talent.

More here.

4. Talk to Customers.  Yes, Your First Week.  As Many As You Can.

They should spend significant time talking to customers directly. This helps them understand the value proposition, objections, and the competitive landscape. A VP of Sales / CRO who doesn’t engage with customers in the first two weeks is setting themselves up for failure.

If they bring up themselves immediately meeting customers when they start — pass.

More here.

5. Recruit Top Talent.  Even Before You Start.

Ideally, bring in 1-2 great reps within the first 30 days, but the groundwork for this starts immediately. If a new CRO / VP of Sales hasn’t started recruiting top talent before they start — they’re not the right fit.  Saying “I’ll hire recruiters” is not good enough.  In fact, it’s a sign of almost 100% failure to come.

The best revenue leaders are constantly building their bullpen.  Not just for their current role, but for the next one too.  Because they’ll always need a team of high performers.  That’s the job.

What Makes a Great VP of Sales and How to Hire One: The Complete Guide

6. Analyze the Pipeline and Metrics.  And Be In All The Top Deals Yourself.

They need to dig into the pipeline, lead flow, and conversion rates. Are there enough leads to hit the plan? If not, they need to address this with the CEO immediately. Signing up for an impossible plan is a recipe for disaster.

And any new VP of Sales / CRO needs to be in deals themselves week 1.  Not just talking about them with the reps in those deals.

More here.

7. Set the Tone and Build Trust

The first two weeks are about establishing credibility, not just “learning”. They need to show the team they’re hands-on, knowledgeable, and ready to lead. This includes being visible, accessible, and decisive.  And it generally includes carrying a bag and selling yourself.  Nothing builds trust more quickly than when a new VP of Sales / CRO closes deals themselves when they start.  Even if later, they mainly coach and support the team.

More here.

If a VP of Sales / CRO doesn’t hit these marks in the first two weeks, it’s a sign they might not be the right fit.

It’s not a strategy and playbook role.  Not at least until $30m, $50m+ ARR.  That’s just a small part of it, the “playbooks”.

The best VPs of Sales and CROs make an impact immediately—not by magic, but by focusing on the fundamentals.

Dear SaaStr: What’s a Good Comp Plan for Our First SDRs?

A good SDR compensation structure should be simple, motivating, and aligned with your business goals. Here’s how I’d structure it:

1. Base Salary + Variable Compensation:  60/40 Or So

SDRs typically have a base salary that makes up 60-80% of their On-Target Earnings (OTE), with the remaining 20-40% tied to performance bonuses. For example, if the OTE is $85k-$95k, the base might be $55k-$70k, and the bonus $20k-$40k, depending on your market and stage.

2. Performance Metrics:  Pick One KPI They Can Control

Bonuses should be tied to metrics SDRs can control, like the number of qualified meetings or sales-qualified leads (SQLs) they generate. For early-stage companies, focus on quantity—getting enough opportunities into the funnel. Over time, as you learn more about your business, you can shift to incentivizing pipeline quality or even revenue sourced

3. Frequent Payouts: Don’t Make Them Wait

Pay bonuses quarterly or even monthly. This timeframe is long enough to smooth out fluctuations but short enough to keep SDRs motivated.  SDRs want quick wins, and pay them quickly.  Without it, it can lead to burnout or disengagement.

4. Clear and Simple Goals.  The Clearer, The Better

The compensation plan should be easy to understand. For example, “Schedule 20 qualified demos per month, completed by an AE partner.” If an SDR can’t explain their comp plan in one sentence, it’s too complicated.

5. Accelerators for Overperformance:  The Best Will Care

Include accelerators for exceeding quota. For example, if the quota is 20 SQLs/month, offer a higher commission rate for every SQL beyond that. This motivates top performers and rewards them for going above and beyond.  It won’t motivate everyone, but it will motivate the best.

6.  Generally, Avoid Tying Bonuses to Closed Revenue — Unless Sales Cycle is Short

SDRs should feel in control of their earnings. Tying bonuses to closed deals can be demotivating since they don’t control whether AEs close the deals. Instead, focus on metrics they directly influence, like SQLs or pipeline generated.  But if the sales cycle is very short (< 30 days), tying to close revenue can work well.

7. Ramp Period: 2-3 Months Is Enough.  It Has To Be

Give new SDRs a 2-3 month ramp period to hit full quota. During this time, they should still earn their base salary and a prorated bonus to keep them motivated while they learn the ropes.

This structure ensures SDRs are fairly compensated, motivated to perform, and aligned with your company’s growth goals. If you’re in a Tier 1 city like SF or NYC, expect to pay 5-20% higher OTEs, and adjust accordingly for remote or international teams.

And a great deep dive on how Rippling does outbound here:

Selling to developers and engineers isn’t like selling to any other buyer. They’re skeptical of salespeople, they value technical depth over flashy demos, and they can smell BS from a mile away. Most startups get this completely wrong.

Ron Gabrisco knows what it takes to get it right. As CRO of Databricks, he’s built one of the most successful developer-focused sales organizations in the world. Here are the 10 biggest mistakes he sees startups make when selling to technical buyers—and how to fix them.

1. Hiring Non-Technical Sales Leaders for Technical Products

The Mistake: Founders think great sales skills translate to any market. They hire proven enterprise sellers without technical backgrounds to lead technical sales.

Why It Fails: “Technical buyers don’t really love talking with salespeople,” Gabrisco explains. “They want salespeople who can add value on the technical front. They don’t even necessarily trust all salespeople.”

The Fix: For technical products with technical buyers, hire sales leaders with engineering backgrounds. At Databricks, most salespeople are technical enough to code, run POCs, and do pilots—not just demos. “Having a technical CRO for a technical company is really important,” says Gabrisco, who has both an MBA and a master’s in engineering from Stanford.

Bottom Line: When founders have PhDs from Berkeley (like Databricks), your sales team needs to speak their language.

2. Trying to Educate Instead of Adding Value

The Mistake: Sales teams think their job is to teach developers about their product through traditional demos and presentations.

The Reality: “What does a salesperson do? They teach your customers how to get value out of your product,” Gabrisco notes. “If you’re not technical enough to understand the product and how it works, it’s hard to teach customers how to get value from it.”

The Fix: Your sales team should understand the technology deeply enough to guide implementation, not just explain features. They should be able to show practical applications and help solve real technical problems during the sales process.

3. Ignoring the Open Source Advantage

The Mistake: Treating open source as a competitor instead of a customer acquisition channel.

The Databricks Way: The founders created Spark, one of the most popular open source projects in the world. Instead of fighting this, they leveraged it. “A lot of our early customers were just open-source free users that we developed relationships with that needed things in the product or needed additional support.”

The Strategy: Build relationships with your open source community first. Understand what they’d pay for. Let adoption drive monetization, not the other way around. “The founding team focused on getting the adoption model right first, not the revenue model,” Gabrisco explains.

4. Underestimating the Power of Technical Founders

The Mistake: Keeping technical founders away from sales conversations because they’re “not sales-oriented.”

The Opportunity: Technical founders are often celebrities in developer communities. Gabrisco tells a story about setting up meetings with Wall Street CIOs: “I would tell them I’m bringing the creators of Spark, and I’d get meetings with CIOs next week—that never happens. We’d show up and 100 people would show up wanting to sign autographs with the founders.”

The Takeaway: Your technical founders might be your best sales asset. Don’t delegate those high-value meetings—do them yourself and bring the founders.

5. Starting with Complex Pricing Models

The Mistake: Trying to capture every dollar with complex pricing from day one.

The Databricks Evolution: “We started with really simple pricing—maybe two SKUs and then an add-on. Now we have fairly complex pricing because we have lots of products.”

The Lesson: Start simple, then evolve. “The tradeoff is: do you make your pricing super simple and make it easier for customers to buy, or do you make it super complex and try to capture every dollar?”

Best Practice: Follow industry standards where possible. Databricks used consumption-based pricing because that’s what AWS, Google, and Microsoft used—it made sense to customers who were already buying cloud services that way.

6. Neglecting Community Building

The Mistake: Focusing only on individual customer relationships instead of building community among users.

The Community Advantage: “Your best selling mechanism is having a really happy customer sell to a prospect,” Gabrisco emphasizes. Databricks leveraged Spark Summit (now Data and AI Summit) to bring thousands of users and customers together.

Early Stage Tactics:

• Product advisory boards
• Industry roundtables
• User meetups
• Customer-to-prospect introductions

Why It Works: Customers want to feel special and be part of the rocket ship. They also want to learn from each other, which creates natural selling opportunities.

7. Underinvesting When You Have Product-Market Fit

The Mistake: Being too conservative with hiring when early signals show strong demand.

Ron’s Regret: “If I had to give myself advice, it would have been invest even more early. I think we could have grown even faster.”

The Signal: When Gabrisco saw the demand from his early enterprise meetings, he hired 40 salespeople in his first quarter. But he wishes he’d hired even more.

The Principle: “When you see you’ve got product-market fit, step on the gas.” Look 12-24 months out based on ramp times and hire accordingly.

8. Not Leveraging VC Networks Effectively

The Mistake: Sending generic asks to investors like “Do you know any CIOs you can introduce me to?”

The Right Way: Make it specific and easy. Instead of broad requests, send targeted emails: “I see you invested in Rippling. Would you mind introducing me to Parker? You can forward this email with a quick blurb about what we do.”

The Databricks Example: A16Z’s Ben Horowitz helped set up enterprise forums where Gabrisco could present to large companies. “Those programs are incredibly valuable. If I can get access to Apple or Capital One’s CIO and their whole staff for 20 minutes, I want to do that myself.”

9. Choosing Wrong Between Inside vs. Field Sales

The Mistake: Thinking you have to choose one model or the other.

The Databricks Approach: “We decided to do both because we saw the opportunity in both.” They built inside sales teams in the bullpen concept (together for energy and learning) while also building enterprise field teams for bigger deals.

The Decision Framework:

• Is your product a big-ticket item needing customization? → Field sales
• Can you start with volume and standardization? → Inside sales
• Can you do both profitably? → Do both

10. Forgetting That Culture Scales Revenue

The Mistake: Focusing only on processes and metrics while neglecting team culture.

Ron’s Top Advice: “Hire the best, inspire them, motivate them, mentor them. Establish your culture early. Hard work beats talent, tons of grit in early days.”

Why Culture Matters: “You need to adapt at each stage if you want to move to the next stage—different leadership, different processes. But the foundation of great people working together stays constant.”

Early Stage Reality: “Getting from zero to 10 million is going to be different than 10 to 100, different than 100 to billion. Early days, it’s a lot of grit and prospecting and pipeline building. Pipeline equals effort.”

The Meta-Lesson: Play to Your Unique Strengths

The biggest takeaway from Databricks’ success isn’t to copy their exact playbook—it’s to identify and leverage your unique advantages.

For Databricks, it was having famous technical founders, a massive open source community, and strong VC connections. For your startup, it might be being Y Combinator alums, having domain expertise in a specific vertical, or having early customers who are influential in their space.

“Take advantage of the unique advantages that you have as a business,” Gabrisco advises. “Figure out what that thing is for your business and really play to your strengths.”

The companies that succeed at selling to developers don’t just hire better salespeople—they build entirely different go-to-market motions that respect how technical buyers actually want to buy.

Ron Gabrisco joined Databricks as CRO when the company had less than $1M ARR and has helped scale it to become one of the largest pre-IPO companies in the world. This post is based on his conversation on his deep dive on the CRO Confidential podcast with Sam Blond.