The plays are the same — but the rules have changed. Here’s what actually matters now.
We’ve been writing about hiring VPs of Sales / CROs for 12+ years (!) at SaaStr. We’ve said — and it’s still true — that about 70% of first VP Sales hires don’t make it past 12 months. That the mis-hired VP of Sales / CRO is the #1 most common mishire in B2B, with a bullet. That getting it wrong costs you a full year, and for most startups, that’s the difference between life and death.
All of that remains true.
But here’s what’s changed: AI has fundamentally transformed what a great VP of Sales / CRO actually needs to do in 2025 and beyond.
We’re seeing 36% of companies decrease their SDR/BDR headcount — the highest reduction of any sales function. Meanwhile, AI SDRs are handling 15,000+ messages in 100 days with 5-7% response rates. The traditional sales playbook is being rewritten in real-time.
So what should you actually look for now?
#1. They Actually Understand AI Sales Tools — And Have Opinions
This isn’t optional anymore.
Ask your VP of Sales candidate: “What AI sales tools have you deployed? What worked? What was overhyped garbage?”
If they can’t fluently discuss AI SDRs platforms like Artisan or Qualified, conversation intelligence platforms like Gong, AI forecasting tools, or even when to use ChatGPT for research vs. when it’s a waste of time — they’re already behind.
The best candidates have battle scars. They’ve tried AI SDRs that sent embarrassingly wrong messages to existing customers. They know which tools actually drive pipeline and which ones just generate impressive-looking dashboards.
Red flag: If they only talk about “leveraging AI” in vague, buzzwordy terms, pass. If they can’t name specific tools they’ve implemented and the ROI they generated, they’re not hands-on enough for your stage.
Green flag: They can articulate exactly which AI tools they’d deploy in their first 90 days — and more importantly, which ones they wouldn’t use yet.
#2. They Can Build a Blended Human + AI Sales Team
Here’s the uncomfortable truth: The traditional SDR role is being decimated by automation.
Your next VP of Sales needs to understand how to architect a team where AI agents handle the volume — prospecting, initial qualification, email sequences, meeting scheduling — while humans focus on complex negotiations, relationship building, and strategic selling.
Ask them: “How would you structure a sales team that uses AI SDRs alongside human reps? Who does what?”
The right answer involves:
- AI agents handling 70%+ of initial outreach and qualification
- Human SDRs/BDRs evolving into “AI operators” who fine-tune messaging and handle edge cases
- AEs freed up from admin work to focus purely on closing
- Clear handoff protocols between AI and human touchpoints
Red flag: They’ve never managed a team using AI agents, or they dismiss AI as “not ready yet.” It’s ready. The question is whether they know how to deploy it.
Green flag: They can explain exactly how AI has changed their team’s productivity metrics — demos booked, response rates, time saved.
#3. They’re Data-Native, Not Just Data-Literate
This has always mattered, but AI raises the stakes exponentially.
AI tools are only as good as the data feeding them. A modern VP of Sales must understand data infrastructure, CRM hygiene, and how to build the foundation that makes AI actually work.
Ask: “Walk me through how you’d set up our CRM and data systems to maximize AI effectiveness.”
They should talk about:
- Clean data as a prerequisite for any AI deployment
- How bad data costs companies up to 25% of potential revenue
- Specific approaches to data enrichment and pipeline hygiene
- Integration architecture between AI tools and your existing stack
Red flag: They see data as “ops work” that someone else handles. In the age of AI, a VP of Sales who doesn’t deeply understand data is like a VP of Sales who doesn’t understand the sales process.
Green flag: They get excited about data infrastructure. They understand that AI forecasting can actually be accurate — if the inputs are right.
#4. They’ve Sold at Your Price Point (Still True, Now Even More Critical)
This classic SaaStr advice becomes more important in the age of AI, not less.
Why? Because AI tools are fantastic at automating transactional, high-velocity sales motions. But enterprise deals — $100K+ ACVs — still require the human judgment, relationship building, and strategic navigation that AI can’t replicate.
If your candidate has only sold $3K/year products, they likely over-relied on automation and may not know how to actually sell. If they’ve only sold $300K/year products, they may not understand how to leverage AI for efficiency at scale.
The question: Has this person actually closed deals at your approximate price point? Not managed people who did — done it themselves?
Red flag: Mismatch of more than 3-5x on deal size in either direction.
Green flag: Clear examples of personally closing deals at your ACV, with specific stories about deal dynamics.
#5. They Have 2-3 People Who Will Follow Them — Including AI-Savvy Execs
The classic SaaStr test: Can they bring anyone great with them?
But here’s the 2026 update: At least one of those people should be someone who actually knows how to run AI sales operations. You need an “AI-native” operator on the team from Day 1.
Ask: “Who would you bring with you? And does anyone on that list have specific experience deploying and optimizing AI sales tools?”
Red flag: They plan to “hire recruiters” to find their first people. Or they don’t have anyone AI-literate in their network.
Green flag: They can name 2-3 specific people — at least one of whom has hands-on AI sales ops experience — and you can verify these people would actually come.
#6. They Still Want to Actually Sell
This one hasn’t changed. In fact, it’s gotten worse.
With all the talk about AI and automation and process, I see more VP of Sales candidates who just want to build dashboards and manage systems. They’ve forgotten that the job is ultimately about winning customers.
Ask them: “What do you want to do your first two weeks on the job?”
If their answer isn’t “meet with customers and understand how we win deals,” pass. Immediately.
The best VP of Sales / CRO candidates in 2026 are excited about using AI to free them up to sell more — not to avoid selling entirely.
Red flag: They talk primarily about “process” and “systems” and “enablement.” They want to observe before engaging with customers.
Green flag: They’re already asking about your top prospects. They want to shadow calls before their start date. They’re itching to get in front of customers.
#7. They Understand the New Economics of AI-Augmented Sales
The math is changing.
A traditional SDR costs ~$90K/year fully loaded. An AI SDR costs $1K-$5K/month and can handle 10x the volume. AI users report being 47% more productive and saving 12+ hours per week.
Your VP of Sales needs to understand these economics and be ready to make hard decisions about team composition.
Ask: “If you had to hit [your quota] with half the traditional headcount but unlimited AI tools budget, how would you do it?”
This isn’t a theoretical question anymore. The best teams are already running 3-4x more efficient than traditional sales orgs.
Red flag: They’ve never done this math. They still think the answer is always “hire more reps.”
Green flag: They can walk through specific scenarios where AI investment replaces headcount investment — and where it doesn’t.
#8. They’ve Built Teams Before (Not Just Managed Inherited Teams)
Still the #1 requirement: Have they hired at least 2-3 reps that performed well?
In the age of AI, this means understanding how to hire for a fundamentally different skill set. The AE of 2020-2024 is not the AE of 2026. Today’s best sales hires need to be:
- Comfortable working alongside AI agents
- Able to focus on high-value activities like relationship building and complex negotiations
- Data-literate enough to understand and act on AI-generated insights
- Adaptable as the technology continues to evolve
Ask: “How has your hiring criteria changed in the last 2 years given AI advances?”
Red flag: They’re still hiring for the same profile they used in 2019.
Green flag: They can articulate specific competencies they now screen for that they didn’t before — and why.
#9. They’re Not Jaded, Broken, or Done
Over the last four years, so much change has happened. The AI disruption is creating a new category of burned-out sales leaders.
They tried AI tools that failed. Their SDR team was cut. They got blamed for not “moving fast enough” on automation. Or they went all-in on AI hype and it didn’t work out.
Now they’re jaded. They dismiss AI as “overhyped.” Or they’re so scarred by failed implementations that they’re paralyzed.
The test: Four minutes into an interview, do they complain about how the CEO/VC/last company “didn’t get it” on AI? Do they seem exhausted by the pace of change?
Don’t hire these people. You need someone who’s energized by the transformation happening in sales — not defeated by it.
Red flag: They blame failures on “the AI tools weren’t ready” or “leadership didn’t support the initiative.”
Green flag: They talk about AI experiments that failed AND what they learned AND what they’d do differently.
#10. They Will Carry a Quota Themselves (At First)
Always true. Even more true now.
With AI handling so much of the sales motion, it’s tempting for a VP of Sales to become a pure “systems architect” — designing workflows, optimizing AI agents, managing dashboards.
But at your stage, you need a player-coach. Someone who will personally close deals while building the infrastructure.
Ask: “Are you willing to carry a quota your first 6 months? What percentage of your time will you spend actually selling?”
The right answer is some version of: “I expect to personally close 20-30% of the deals while I’m building the team and systems.”
Red flag: They’re reluctant to get their hands dirty. They want to “assess” before selling.
Green flag: They’re already calculating how many deals they’d need to close personally to hit the number.
The Bar Has Gone Up, The Teams Have Changed
The best VP of Sales / CRO in 2026 isn’t someone who’s either “a great traditional sales leader” OR “an AI expert.”
They’re someone who:
- Deeply understands traditional sales fundamentals (team building, deal mechanics, customer relationships)
- AND has real, battle-tested experience deploying AI tools that actually work
- AND is energized — not exhausted — by the transformation happening
These people exist. They’re rare. And if you find one, you need to move fast.
Because here’s what hasn’t changed: 8 out of 10 first VP Sales hires still fail. The consequences of getting it wrong — losing a year of your startup’s life — are still devastating.
But what has changed is this: Get it right with an AI-savvy VP of Sales, and you can build a sales engine that operates at 3-4x the efficiency of your competitors.
The stakes have never been higher. Neither has the upside.
