One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. I updated it in 2025. I’m updating it again for 2026, because the world has changed even more.
We’re now in a world where AI agents handle a meaningful chunk of the pipeline. Where reps are measured against an AI baseline, not just last year’s plan. Where the best VPs of Sales are running hybrid human-plus-agent teams, and the worst ones don’t even know what Clay or Artisan or Qualified actually do. Title inflation is worse than ever (every VP wants to be a CRO, every CRO wants $500K base). And capital is still finite for almost all of you.
So the original questions still hold. But the bar is higher. And you have to screen for AI fluency, not just sales fluency.
Before You Hire a VP of Sales: Prove the Motion First
Same advice as always, with one 2026 twist:
- Hire 1-2 sales reps before you hire a VP of Sales. Make them successful first. Both hitting quota.
- Or, in 2026, get to $1M-$2M ARR with founder-led sales plus AI SDRs. Artisan, Monaco, Clay-built agents, whatever you use. If you’ve proven the motion works with you closing and agents prospecting, that counts now too.
- Either way, don’t outsource figuring it out. A VP of Sales’ job is to scale sales. Not to figure it out from scratch. Not usually.
If you skip this step, you’ll fire whoever you hire in 9 months. Every single time. I’ve seen it 100 times. There are no exceptions.
OK. Now if you’re ready, here are 15 screening questions to see whether you have a real VP of Sales candidate in hand, or not.
The 15 Questions
These questions mostly don’t have right or wrong answers. They’re designed to create dialogue and surface whether you have a real VP candidate or someone who just has the title on LinkedIn.
Give the candidate enough data ahead of time (ARR, growth rate, headcount, motion, current AI stack) so they can answer with substance. If they didn’t do the homework before the interview? That’s your answer right there.
1. How big a team do you think we need right now, given what you know?
If they can’t answer, right or wrong, pass. They should at least be in the range.
In 2026, the right answer is often smaller than it would have been in 2023. If they’re pitching you 20 SDRs when 4 SDRs plus an Artisan deployment would do the same job, that’s a tell. They’re playing the old playbook.
2. What deal sizes have you sold to, on average and range?
If it’s not a similar fit to you, probably pass. If they can’t answer fluidly, pass.
A $500K ACV closer is rarely going to thrive in a $15K ACV velocity motion. And vice versa. The motions are different. The skills are different. The hiring profiles are different. Don’t fight physics here.
3. Tell me about the teams you’ve directly managed, and how you built them.
If they can’t describe how they built and recruited at least a small team, pass. 50% of the job of VP of Sales is recruiting. This has not changed in 2026. AI doesn’t recruit your reps for you. Your VP does.
If they only describe a team they inherited, that’s not the same thing. Ask specifically about the reps they hired, and where they found them.
4. What sales tools have you used? What’s worked? What hasn’t?
This was always important. In 2026 it’s a critical filter, not a soft one.
If they don’t have strong opinions on Clay, Apollo, Gong, Outreach, Salesloft, Artisan, Qualified, Salesforce, HubSpot, and whatever else you use, they’re not hands-on enough. If everything they describe is pre-2024 and pre-AI, be worried. Very worried.
The right candidate should be able to walk you through their current stack, what they killed, what they added, and why. If they can’t, they’re not actually running sales today. They’re managing reports about sales.
5. How are you using AI agents in your current sales motion? (NEW)
This is the most important new question on the list. If they hedge, pass. If they say “we’re exploring it,” pass. If they say “I leave that to ops,” pass.
The right answer in 2026 sounds like: “We run Artisan for outbound at the top of funnel, Qualified for inbound chat, Gong for call analytics, Clay for enrichment, and we just deployed an Agentforce win-back agent that’s running 72% open rates. Here’s what’s worked and here’s what hasn’t.”
If your candidate isn’t fluent here, they’re going to be an expensive observer of what your competitors are doing. And your competitors are not waiting.
6. How has your ideal rep profile changed in the last three years? (NEW)
Listen for evolution.
The best VPs have moved their hiring bar. They’re hiring fewer SDRs (because agents handle a lot of prospecting). They’re hiring AEs who can run their own AI workflows. They’re cutting the bottom 20% faster because AI raises the floor on what an average rep can produce.
If they describe the same rep they hired in 2022, they haven’t been paying attention. The profile has to change. The reps you need now are not the reps you needed in 2022.
7. Who do you know right now that would join you on our sales team? If things progress, can I talk to them? [They just have to pass this test]
All good candidates should have names in mind. Tell me about them, by background if not name.
If they don’t have a single person they’d recruit, they’re not a real leader. They’re a manager who got promoted into something they don’t actually do. Real VPs build a bench wherever they go. Fake VPs are just looking for the next title.
Bonus: ask if any of those people will hop on a call with you. Real VPs say yes. Fake VPs find a reason to delay.
8. How should sales and post sales work together?
This will ferret out how well they understand the true customer lifecycle.
For 2026, add: how do you think about FDEs or other humans ensuring AI Agents and AI products are rolled out properly?
9. How do you think about SEs, FDEs, and CS as three distinct roles in an AI sales motion?
This is the single most important technical-org question in 2026, and most VP Sales candidates will fumble it.
A real VP Sales today understands these are three different jobs, not one blob:
- SE (Sales Engineer): Pre-sale. Demos, technical Q&A, security review, RFP responses, proof-of-concept design. A lot of the traditional SE workload (demo prep, ROI modeling, proposal generation, technical Q&A) is being done by AI agents in 2026, so the SE team is smaller than it used to be but more senior. Real SEs in 2026 are architects, not demo monkeys.
- FDE (Forward Deployed Engineer): This is the role most 2022-era VP Sales candidates have never managed and don’t understand. FDEs are engineers who embed with the customer post-sale to actually deploy the product, write integration code, build custom workflows, tune the agents on real customer data, and make the deal go live in production. Palantir invented the model. Every serious AI-native B2B company (OpenAI, Anthropic, Sierra, Glean, Hebbia, Decagon, Crescendo, Harvey, and on and on) runs FDEs now. They are the reason those companies are winning enterprise deals at speed. Without an FDE motion, complex AI deals stall at the pilot stage. Forever. The pilot never goes to production. The deal never expands. The renewal is at risk. FDEs are how you actually land AI deals in 2026, period.
- CS (Customer Success): Post-deployment. Adoption, expansion, renewal, relationship management, QBR cadence. CS is not the same as FDE. CS is not writing integration code. CS is not tuning agents. CS is not building custom workflows. If a VP Sales conflates the two, they don’t understand the modern motion.
Ask the candidate specifically: “When does an FDE get involved in a deal? Who owns the FDE team, sales or product or services? How are FDEs comped? When do they hand off to CS? What’s the FDE-to-AE ratio in your org?” If they don’t have crisp answers, they have not run an AI sales motion. They’ve run a 2022 sales motion. Pass.
Bonus filter: ask if they’ve ever lost a deal, or watched a pilot die, because the FDE motion broke down. Anyone who has actually shipped real AI products has stories here. If they don’t, they were not in the room where it happened.
10. How do you deal with FUD in the marketplace?
Especially relevant in 2026 with so much AI category confusion. Buyers are fatigued. Everyone claims to be “AI-powered” or “AI-native.” Half the time those claims are nonsense.
How does the candidate cut through? If their answer is generic, their reps will lose the close. If they have a real framework (proof, references, pilots, ROI math), they can compete.
11. Do you work with forward deployed engineers, sales engineers and sales support? What role do they play at this stage when capital is finite?
This will ferret out whether they can play at an early-stage B2B startup successfully, and whether they understand how to scale once you scale.
So many candidates can’t actually run a demo or answer the harder technical questions themselves. They need a five-person support cast just to do a pitch. At your stage, that’s a non-starter.
For 2026: also ask if they think technical sellers can replace traditional SEs at certain ACV levels. The good candidates have thought about this and have a real answer.
12. What will my revenues look like 120 days after I hire you?
Have them walk you through it. There’s no correct answer. But there are many wrong answers.
“We’ll see” is a wrong answer. “I’ll know after my first 60 days” is a wrong answer. “I never give numbers in interviews” is a wrong answer.
They should be able to construct a plausible scenario. They should ask clarifying questions. They should show you they’ve thought about ramp time, the existing pipeline, and the realistic outputs of the team they’d inherit plus whoever they’d hire.
13. How should sales and marketing work together at our phase?
This will ferret out if they understand lead generation and lead funnel mechanics. Most candidates don’t, unless they were really a VP of Sales before. Believe it or not.
For 2026: also ask how they’d integrate marketing’s AI agents (Qualified, Clay enrichment, Common Room signals, etc.) into the sales motion. The line between marketing and sales agents is now blurry. The best VPs know how to run that seam. The worst ones still think marketing is just a vendor to sales.
14. What would you do your first two weeks on the job?
Really listen here. If they say, unprompted, that they’ll go visit customers? That’s great. That’s what you want. That’s the answer.
If all they talk about is process, dashboards, RevOps tooling, and “building the foundation”? You’re not ready for that hire. You may never be ready, in fact. The candidates who lead with process and not customers are the ones who get fired in year two. Every time.
15. Are you still willing to sell yourself? (UPDATED, NOW CRITICAL)
This was always on the list. In 2026 it’s existential.
Look, your VP of Sales can’t be a quota-carrying rep forever. But way too many VPs now want to manage from a strategic altitude. They want to “build the team,” “set the strategy,” and “enable the reps.” They don’t want to take a call. They don’t want to run a close. They certainly don’t want to do a demo.
That hire fails. Every time.
Especially in a world where your AI agents are doing more of the volume, your humans need to do the highest-value stuff. That includes your VP being in the biggest deals, every quarter, forever. The best VPs of Sales I know still personally close the biggest renewal and the biggest new logo. Every single quarter.
If they balk at the question, pass. If they say “of course,” and then describe specific deals they’re personally closing right now? You may have a real one.
What These Questions Will Surface
None of these questions are particularly profound in isolation. Hopefully they’re kind of obvious.
But together, they create the right dialogue. From the dialogue, you’ll be able to determine:
- Whether this candidate is for real, or not
- Whether they can be a true leader and take you to the next level, or not
- Whether they’re a fit for your company, your space, and the 2026 economic reality
If any of the answers aren’t good enough, trust me, just pass. If any don’t make sense, pass. And if you know more about any of these questions than the candidate does, pass.
Your VP of Sales needs to be smarter than you in sales, sales processes, AI-augmented selling, recruiting, and building and scaling a team. If they aren’t, they’re not your VP. They’re an expensive seat-warmer with the title.
The 2026 Cheat Sheet
Quick reference for screening calls. Print this out:
- How big a team do we need right now?
- What deal sizes have you sold to?
- Tell me about the teams you’ve built and how you recruited them.
- What sales tools have you used, what worked, what didn’t?
- How are you using AI agents in your sales motion today?
- How has your ideal rep profile changed in the last three years?
- Who do you know that would join you on our sales team?
- How should sales and customer success work together?
- Tell me about deals you’ve lost to competitors.
- How do you deal with FUD in the marketplace?
- How should FDEs, SEs and sales support work at our stage?
- What does revenue look like 120 days in?
- How should sales and marketing work together?
- What would you do your first two weeks on the job?
- Are you still willing to personally sell?
Use this. It works. And in 2026, the cost of getting this hire wrong is higher than it’s ever been. The right VP of Sales is a force multiplier on top of your AI agents. The wrong one is an expensive layer of management that slows you down.
Pick carefully.
More on why these matter here:
