Due Diligence Before You Take the VP Sales Role: A Framework

Eighteen months. That's the average tenure for a VP Sales. Not because VP Sales leaders are uniquely bad at their jobs. Because the role is uniquely dependent on factors that exist before you walk in the door. The pipeline you inherit. The team you didn't hire. The quota the board set without your input. The founder who says they want a sales leader but actually wants someone to execute their playbook without questioning it.

Most VPs who flame out at the 12-to-18-month mark didn't fail at selling. They failed at due diligence. They took a role based on the pitch deck version of the company rather than the operating reality. They got excited about the title, the comp package, the equity story. They didn't ask hard questions. Or they asked and accepted vague answers.

I've been tracking executive sales job postings weekly since 2025. The dataset now covers 1,298 postings across Healthcare (720), Tech/Software (719), Education (626), and Financial Services (589). Of those, 636 are VP-level roles with disclosed compensation. The patterns in this data are useful for anyone evaluating a VP Sales opportunity. Some of those patterns are warning signs hiding in plain sight inside the job posting itself.

This is a framework for doing proper due diligence before you accept. Six steps. Each one covers a specific dimension of risk that most candidates don't evaluate until they're already three months in and realizing the job they accepted isn't the job they interviewed for.

Step 1: Financial Health

Before you evaluate the role, evaluate the company's ability to support it. A VP Sales without budget, runway, or a product that converts is an expensive individual contributor with a nice title.

Burn Rate and Runway

Ask directly: what's your current monthly burn rate, and how many months of runway do you have? Eighteen months of runway is the minimum you should be comfortable with. Anything less and you're signing up for a company that will be fundraising during your first year. Leadership attention will be split between your sales plan and investor meetings. Your hiring budget may get frozen mid-quarter. The strategic priorities you were hired to execute will shift based on what investors want to hear.

If the company is pre-revenue or early-revenue, burn rate tells you how fast the clock is ticking. A company burning $800K/month with $12M in the bank has 15 months. You won't even be fully ramped before they need to raise again. That's a fundamentally different risk profile than a company burning $400K/month with $18M in the bank.

For later-stage companies, the question shifts from runway to unit economics. What's the burn multiple? How many dollars does the company burn for every dollar of new ARR? A burn multiple above 2x at Series B or later means the go-to-market engine isn't working efficiently. You're being hired to fix something that may be structurally broken at the product or market level, not just the sales level.

Revenue Trajectory

Ask for the revenue trajectory over the last 12 months. Not the projections. Not the board deck. The actuals. Month by month, what did the company close? If they're growing 15% quarter-over-quarter, that's a conversation about acceleration. If they've been flat for six months and are hiring a VP Sales to "unlock the next phase," that's a conversation about whether the problem is actually solvable by a sales hire.

Flat or declining revenue before a VP Sales hire often means the company needs someone to blame when things don't turn around. That's pattern recognition from watching hundreds of these roles turn over. It doesn't mean you shouldn't take the job. It means you should negotiate your ramp timeline, guarantee your first two quarters of variable comp, and set explicit performance milestones that account for the state of the business when you arrived.

Funding Stage Context

The funding stage tells you what you're walking into. Our data tracks roles across every stage, and the VP Sales role changes fundamentally at each one.

Funding Stage	VP Base Range	What You're Building
Seed / Series A	$193K - $260K	Sales motion from scratch
Series B / C	$180K - $270K	Scaling existing motion
Enterprise / Public	$168K - $266K	Optimizing and managing at scale

Seed/Series A VPs in our data average $193K-$260K in base. That's actually the highest VP base range by stage, which might seem counterintuitive until you realize these companies are competing for experienced leaders willing to take startup risk. The comp has to offset the uncertainty. If a seed-stage company offers you $150K and says the equity makes up the difference, run the math on what that equity needs to be worth. Usually the equity story doesn't hold up unless the company reaches a $500M+ outcome, and the probability of that at seed stage is below 10%.

Enterprise and public company VPs average $168K-$266K in base. Lower floor, but the package includes RSUs, guaranteed bonus structures, and the stability of a company that won't disappear in 18 months. The risk-adjusted total comp often beats the startup offer.

Step 2: Predecessor Intel

The single most predictive data point for your success in a VP Sales role is what happened to the person who held it before you. And the person before them.

Why Did the Last VP Sales Leave?

There are three scenarios, and each tells you something different:

• They were promoted or moved to a bigger opportunity. Good sign. The role served as a launching pad. The company supports career growth. The sales org was left in decent shape for you to build on.
• They were let go for performance. This is where nuance matters. Were they genuinely underperforming, or did they inherit an impossible situation? Did the board set unrealistic targets? Did the product change mid-year? A VP who "missed quota" at a company where nobody has ever hit quota isn't a performance issue. That's a company issue you're about to inherit.
• They quit. Find out why. Burnout? Culture conflict with the CEO? A strategic disagreement about market focus? A VP Sales who quits inside of a year almost always has a story, and that story is directly relevant to your decision.

How to Find Out

LinkedIn is your first stop. Find the previous VP Sales. Look at their tenure. See where they went. A lateral move to a similar-stage company suggests they were pushed out or hit a ceiling. A step up to a CRO role suggests natural progression. A move to a completely different industry or function suggests burnout or a desire to escape a bad situation.

Reach out directly. Most former VPs will talk candidly, especially if they left on bad terms. They have no incentive to protect the company. Buy them coffee. Ask open-ended questions. Let them talk.

Also talk to people who reported to the previous VP. AEs and directors who stayed through the leadership transition have a ground-level view of what went wrong and what the company is actually like to sell for. If you can get a current AE on the phone before you accept, do it. The way a company reacts to that request is itself a data point.

The Revolving Door Test

Ask the company directly: how many VP Sales have you had in the last five years? If the answer is three or more, you're looking at a systemic problem. The issue isn't the individual leaders. It's the role, the expectations, or the leadership above you. Companies with high VP Sales turnover typically have one of three problems: a CEO who won't let go of sales decisions, a board that sets fantasy quotas, or a product that doesn't sell as well as the pitch deck suggests.

Two VPs in five years is normal. Three is a yellow flag. Four or more is a pattern you should assume will repeat with you unless something fundamental has changed, and "we hired you" is not a fundamental change.

Step 3: Board Composition

The board sets your quota, approves your budget, and decides whether you stay or go. Understanding who sits on that board and what they know about building a sales organization is survival information.

Sales DNA on the Board

Look up every board member. Check their backgrounds. How many have ever carried a bag, managed a sales team, or built a go-to-market org? If the answer is zero, you'll spend a meaningful portion of your time educating the board on how sales works. That's time you won't spend building pipeline or coaching your team.

A board with at least one member who has direct sales leadership experience will give you more realistic targets, more appropriate timelines, and more useful strategic guidance. A board of engineers and finance operators will judge your performance through frameworks that don't always apply to commercial functions. They'll expect linear growth curves. They'll question why deals slip. They'll compare your conversion rates to benchmarks from a blog post without understanding your market dynamics.

Check the investor profiles too. Some VC firms have operating partners with go-to-market expertise who sit on boards or advise portfolio companies. Knowing whether your board investor has that kind of support system matters.

Founder-Led Sales History

At Seed and Series A companies, ask whether the founders have been doing the selling. If they have, understand what that means for you. Founder-led sales creates a specific set of expectations that are often unrealistic for a hired VP. Founders close deals based on vision, personal relationships, and the ability to make product commitments on the spot. You won't have that leverage. Your close rates will be different. Your deal cycle will be different. Your average contract value will be different.

If the founders haven't been selling and they're hiring you to start the function from nothing, that's a different challenge. You're building a repeatable motion without proof points. Ask what evidence exists that the product sells. Customer conversations? Inbound interest? LOIs? Design partners paying anything? A VP Sales hire with zero sales traction is a bet on the product, and you need to believe in that bet with the same conviction you'd have if you were investing your own money. Because you are: your time, your reputation, and your next 18 months.

How the CEO Thinks About Sales

The CEO-VP Sales relationship is the most important dynamic in the company for your success. During the interview process, assess how the CEO views sales as a function. Do they see it as strategic or as a cost center? Do they understand that building a sales org takes time, or do they expect revenue on your second Monday?

Ask the CEO directly: "When we disagree on go-to-market strategy, how do you see that playing out?" The answer reveals whether you'll have actual authority or just a title and a quota.

Step 4: Sales Org Reality

There's a massive difference between inheriting a functional sales org and building one from scratch. Both are valid VP Sales jobs. They require different skills, different timelines, and different comp structures. Make sure you know which one you're walking into before you sign.

Building vs. Inheriting

If you're building: What's the hiring budget for year one? What's the expected timeline for your first hire to be productive? What sales tools and infrastructure exist? Who has been handling sales until now, and what does the handoff look like?

If you're inheriting: What's the current team size and structure? What's the average tenure of the existing AEs? How many are above plan, at plan, and below plan right now? Have there been any departures in the last 90 days you should know about?

Inheriting a team sounds easier than building one. Sometimes it is. But inheriting a team built by someone with a different philosophy, different hiring standards, or different performance expectations can be harder than starting fresh. You may need to make changes, and the company's appetite for turnover in the sales org will determine how quickly you can move.

Quota Attainment History

This is the most important operational data point you can ask for. What percentage of the sales team hit quota last year? And the year before?

If less than 40% of the team hit quota, the quota is wrong, the team is wrong, or the product-market fit isn't there. Whatever the cause, you're walking into a situation where the existing playbook doesn't work. Rebuilding it takes time. Make sure the company has built a realistic ramp timeline into your performance expectations and is willing to guarantee your variable comp while you make changes.

If 60-80% hit quota, you're looking at a healthy org. Your job is to optimize: get the bottom performers up or out, protect the top performers, and find the operational leverage that takes the team from good to exceptional. That's a manageable mandate with a clear path to hitting your own number.

If nobody has ever hit quota at this company, you need to ask why they think hiring you changes that.

Tech Stack and Process Maturity

The sales tech stack reveals how mature the operation is. A company running Salesforce with defined pipeline stages, activity tracking, and forecasting reports has invested in sales infrastructure. A company tracking deals in a spreadsheet has not. Neither is inherently bad, but they represent very different starting points and very different amounts of foundational work for your first 90 days.

Ask about the current stack. CRM, engagement platform, conversation intelligence, forecasting tools. More importantly, ask who selected those tools and whether the team uses them. A $200K/year Salesforce instance with 30% adoption is worse than a well-configured HubSpot that everyone lives in.

Step 5: Comp Analysis

You can't evaluate a VP Sales offer without market data. Gut feeling and "what my friend got at that Series B" aren't benchmarks. Here's what the data shows across 636 VP-level roles with disclosed compensation.

VP Sales Base Salary Benchmarks

The average VP Sales base salary in our dataset ranges from $167K to $251K. That's a wide band because "VP Sales" covers everything from a first sales hire at a seed company to a VP running a 100-person org at a public company.

Metric	Low End	High End
Avg VP Sales Base	$167K	$251K
Seed / Series A VP	$193K	$260K
Enterprise / Public VP	$168K	$266K

The top-paying VP Sales roles in our data are significant outliers worth noting. Fieldwire posted a Seed/Series A VP role at $400K-$600K. HPE listed an Enterprise VP at $305K-$652K. Thomson Reuters came in at $322K-$598K. These are real postings, but they represent the extreme top of market. Don't use them as your baseline. They're useful for understanding the ceiling, not the floor.

Only 54.8% of all postings in our dataset disclose salary. The other 45.2% hide behind "competitive compensation" or "commensurate with experience." That non-disclosure is a signal. Companies paying at or above market lead with their numbers because it's a recruiting advantage. Companies that don't disclose are, on average, paying less.

What to Negotiate Beyond Base

Base salary gets the most attention, but three other components deserve equal scrutiny:

• Variable comp structure. Is it commission on team bookings, MBO-based bonus, or a hybrid? The structure tells you what the company values. Heavy MBO weighting means they want a strategic operator. Heavy commission weighting means they want a number. Ask what the average VP-level payout was as a percentage of target last year. If it was 60%, your OTE isn't really your OTE.
• Equity details. Vesting schedule, strike price, exercise window, acceleration on change of control. A 90-day post-termination exercise window at a pre-IPO company means your equity evaporates if you leave or get pushed out. Ask about extended exercise windows. Some companies now offer 5-10 years. That's real value.
• Guaranteed variable for the first two quarters. If you're starting with no pipeline and a 90-day sales cycle, your first two quarters of variable should be guaranteed at plan. Any company that pushes back on this is expecting you to inherit pipeline that doesn't exist or close deals faster than the cycle allows. Neither of those things is realistic, and their unwillingness to guarantee tells you something about how they think about the ramp.

Step 6: Red Flags in the Job Posting

The job posting is the company's first communication with you. What they say, and what they leave out, is diagnostic. We've analyzed language patterns across 1,298 executive sales postings. Certain phrases appear repeatedly in roles that correlate with higher turnover and less organizational support for the sales leader.

Red Flag Phrase	Frequency	What It Usually Means
"Fast-paced environment"	248 mentions	Organizational chaos, shifting priorities
"Competitive compensation"	198 mentions	Below-market pay, no disclosed range
"Self-starter"	85 mentions	No existing sales infrastructure or support
Travel 50%+	45 mentions	Territory gaps, no inside sales motion
"Scrappy"	8 mentions	Under-resourced, no budget for the team
"Wear many hats"	4 mentions	Undefined role scope, no support functions

"Fast-Paced Environment" (248 Mentions)

This is the most common red flag phrase in our dataset, appearing in 248 of 1,298 postings. Nearly one in five. At the individual contributor level, "fast-paced" might just mean the company moves quickly. At the VP level, it signals something more specific: shifting priorities, reactive leadership, and an expectation that you'll absorb chaos rather than having the space to build systematically.

A VP Sales needs stability to build process, hire well, and let a sales motion mature. "Fast-paced" at the executive level often means the company won't provide that stability. Ask during interviews: "How many strategic priorities has the company had in the last 12 months? How many of those changed mid-year?" The answers will tell you whether "fast-paced" means high-growth velocity or organizational whiplash.

"Competitive Compensation" (198 Mentions)

198 postings used the phrase "competitive compensation" without disclosing a salary range. That's 15% of all postings in our dataset. Meanwhile, 54.8% of postings do disclose salary. The ones that don't are actively choosing opacity.

Companies paying at or above market want you to know it. The salary number is itself a recruiting tool. When a posting says "competitive" without a number, it's usually because the number wouldn't compete. Ask for the range early in the process. If they won't provide it after the first conversation, they're either below market or haven't defined the level of hire they're looking for. Both are problems.

"Self-Starter" (85 Mentions)

Every VP Sales is a self-starter. When companies include it in a VP-level posting, they're signaling something else: there's no existing infrastructure for you to build on. No sales playbook. No onboarding process. No CRM workflows. Minimal marketing-generated pipeline. You're building from zero with limited support.

That can be the right job if you want it and the company has priced that difficulty into the comp. But if "self-starter" appears alongside a below-market base and no equity disclosure, you're being asked to take on founding-level difficulty for middle-management compensation.

Travel 50%+ (45 Mentions)

Forty-five postings required travel above 50%. For a VP Sales, heavy travel requirements usually mean one of three things: the company lacks an inside sales motion and needs the VP in the field closing deals, the customer base is geographically scattered without regional coverage, or the company conflates the VP Sales role with a senior account executive role.

If the travel requirement exists because you're expected to be the top closer, ask yourself whether that's really a VP role or an IC role with a VP title. Your job should be building and managing the team. If travel is about strategic customer relationships and market presence at the executive level, that's appropriate and potentially valuable.

"Scrappy" and "Wear Many Hats" (12 Combined)

"Scrappy" appeared 8 times. "Wear many hats" appeared 4 times. Both signal the same thing: under-resourced, and the VP Sales is expected to fill multiple roles simultaneously. VP, first AE, sales ops, SDR manager, and possibly enablement lead. All at once.

At a seed-stage company with fewer than 20 employees, that might be expected and priced into the comp. At Series B or later, these phrases suggest the company hasn't invested in go-to-market infrastructure despite having the funding to do so. That's a strategic choice that tells you how leadership values the sales function.

The Questions to Ask

Here's the consolidated checklist. Not all of these belong in a single conversation, but over the course of an interview process you should have answers to all of them before you sign anything.

Financial Health

• What's your current monthly burn rate?
• How many months of runway do you have at current burn?
• What's the revenue trajectory over the last 12 months, actuals not projections?
• When do you expect to raise again, and at what terms?
• What's the current ARR and net revenue retention rate?

Predecessor and History

• How many VP Sales have you had in the last five years?
• What happened with the last one? And the one before that?
• What's the average tenure of your executive team?
• Can I speak with the previous VP Sales?

Board and Leadership

• Who on the board has direct sales or go-to-market experience?
• Who sets the annual sales targets, and what's the methodology?
• How frequently does the board review pipeline and bookings?
• When we disagree on sales strategy, how does that get resolved?

Sales Org and Operations

• What's the current team size and structure?
• What percentage of the team hit quota last year?
• What's the current sales tech stack, and what's the adoption rate?
• What does pipeline generation look like? Inbound vs. outbound split?
• Can I talk to two or three current AEs before I accept?
• What's the average deal size, cycle length, and win rate?

Compensation and Expectations

• What's the base salary range for this role?
• What's the variable structure, and what did the average VP-level payout look like last year?
• What's the equity grant, the current 409A valuation, and total shares outstanding?
• What's the expected ramp timeline before you evaluate my performance against quota?
• What does success look like at 6 months, 12 months, and 18 months?

Putting It Together

No company passes all six areas perfectly. That's not the point. The point is knowing where the risks are before you accept, so you can negotiate around them, build your 90-day plan to address them, or walk away informed rather than blindsided at month four.

A company with shaky financials but a strong board and realistic expectations might be worth the risk. A company with great funding but three VPs of Sales in two years has a structural problem that money won't fix. A company that checks every box but won't disclose comp is telling you something about how they value the sales function relative to other functions.

The framework isn't pass/fail. It's a way to see the full picture before you commit. Most candidates do extensive diligence on the company's product, market, and competitive positioning. Fewer do diligence on the operating environment they're about to step into. The operating environment is what determines your success or failure as a VP Sales.

Eighteen months. That's the average. Every VP Sales who got pushed out at month 14 thought they'd be the exception. Some of them were right about the opportunity and wrong about the operating environment. The due diligence is how you avoid becoming that cautionary tale on someone else's LinkedIn feed.