Key Takeaways:

60-70% of VP of Sales hires fail within 18 months, costing companies $200,000-$500,000 in wasted investment.
The failure is usually not the VP's fault. It is a mismatch between what they were hired to do (scale) and what you needed (build).
Seven warning signs appear within the first 90 days that predict failure with 90% accuracy.
A Fractional Sales Leader can either rescue the situation by building the missing infrastructure or replace the VP cost-effectively.

The $250,000 Mistake You Cannot Afford to Make Twice

Three months ago, you were thrilled. You finally hired a VP of Sales.

She came from Salesforce. She has a great LinkedIn profile. She interviewed well. She had all the right buzzwords: "pipeline acceleration," "revenue operations," "go-to-market strategy."

You paid her $200,000 base salary plus equity. You gave her a corner office (metaphorically, since you are remote). You told the team she was going to "transform" the sales organization.

Today, you are terrified.

Nothing has changed. Revenue is flat. The pipeline is messy. The team is confused. And when you ask her what is happening, she gives you polished answers that sound smart but mean nothing.

You are three months and $50,000 into this hire, and you can feel it in your gut: This is not working.

But you cannot afford to fire her yet. You need to give it more time, right? The recruiter said it takes six months to ramp. Your board will ask tough questions if you fire another VP.

So you wait. And the bleeding continues.

Here's what I know: If you are seeing the warning signs, waiting will not fix them. You need to act now, or this $250,000 mistake will become a $500,000 disaster.

Let me show you the seven warning signs that predict sales VP failure. More importantly, what you can do to salvage the situation before it is too late.

Why VP of Sales Hires Fail (It Is Usually Not Their Fault)

Before we diagnose the problem, let's be clear about the root cause.

Most VP of Sales failures are not because the VP is incompetent. The failures because the founder hired a driver when they needed a builder.

Drivers vs. Builders

A Driver is someone who optimizes an existing machine. They take a functioning sales engine and make it 20% more efficient. They tweak the comp plan, refine the pitch, optimize the CRM workflows.

Drivers come from big companies where the infrastructure and endless support already exists: established CRM systems, documented playbooks, dedicated RevOps teams, marketing that generates qualified leads.

A Builder is someone who constructs the machine from scratch. They create the playbook, configure the CRM, hire the first reps, define the sales stages, and document everything so it can scale.

Builders come from early-stage companies where they had to figure things out with limited resources.

The Mismatch

Most $1M-$10M ARR companies need a Builder.

But when they go to hire, they get seduced by the "brand name" VP from Oracle or HubSpot. That person is a Driver.

The result: The Driver shows up expecting a machine to optimize. Instead, they find chaos. No documented process, incomplete CRM data, reps who "wing it," and a founder who has been the Super Closer for three years.

The Driver does not know how to build from zero. They freeze. They start asking for resources ("We need a full-time BDR team and a marketing automation platform") without fixing the fundamentals.

Three months pass. Six months. A year. And nothing improves.

The 7 Warning Signs Your VP of Sales Is About to Fail

These signs are predictive, not reactive. If you see 3 or more of these in the first 90 days, your sales VP hire will almost certainly fail without intervention.

Warning Sign #1: They Are Spending More Time on "Strategy" Than Execution

What It Looks Like:

Your VP is constantly in meetings. They are working on a "Go-to-Market Strategy Deck." They are researching "best practices." They are talking to consultants about "sales enablement platforms."

Meanwhile, your sales reps do not know what they are supposed to do differently.

Why It Is a Red Flag:

Strategy without execution is procrastination. At the $1M-$10M stage, you do not need a 40-slide PowerPoint on your Total Addressable Market. You need someone to:

Listen to call recordings and fix broken pitches
Run daily standups to move deals through the pipeline
Train reps on objection handling

If your VP is spending more than 20% of their time on strategy in the first 90 days, they are avoiding the hard work of execution because they do not know how to do it.

What You Should See Instead:

In the first 90 days, your VP should be in the trenches:

Listening to every sales call
Running weekly pipeline reviews
Rewriting email templates
Coaching reps in real-time

Strategy comes after you have stabilized the fundamentals.

Warning Sign #2: They Keep Asking for More Resources Before Fixing the Fundamentals

What It Looks Like:

"We need to hire three more BDRs."

"We need to invest in Outreach.io and ZoomInfo."

"We need a full-time Sales Ops person to clean up the CRM."

Every conversation with your VP ends with them asking for more budget, more headcount, more tools.

Why It Is a Red Flag:

Throwing resources at a broken system does not fix it. It just makes the problem more expensive.

A great VP will say: "Before we hire anyone else, let me fix the process with the team we have. Once I prove the model works, then we will scale."

If they are asking for resources without first demonstrating that they can improve outcomes with the current team, they are either incompetent or trying to deflect blame.

What You Should See Instead:

A great VP identifies quick wins with existing resources:

"I am going to rewrite the discovery call script and train the team on it this week."
"I am cleaning up the CRM stages so we can actually forecast accurately."
"I am implementing a weekly pipeline review cadence starting Monday."

Resource requests should come AFTER they have proven they can execute, not before.

Warning Sign #3: The Team Does Not Respect Them (Turnover Increases)

What It Looks Like:

Your top rep starts interviewing elsewhere. Your SDR tells you in a 1:1 that "the new sales VP does not get it." Team morale drops.

Voluntary turnover in the first six months of a VP hire is the clearest leading indicator of failure.

Why It Is a Red Flag:

Sales teams smell weakness. If your VP is not respected, reps will not follow their direction.

Lack of respect usually comes from one of two sources:

Incompetence: The VP does not understand the product, the market, or the sales process
Inauthenticity: The VP talks a big game but does not follow through

Either way, once the team loses confidence, it is nearly impossible to regain.

What You Should See Instead:

A great VP earns respect by demonstrating competence immediately:

They join sales calls and close deals alongside the team
They give specific, actionable coaching (not generic advice)
They protect the team from unrealistic founder expectations

If reps are saying "I am learning so much from the new sales VP," you made a good hire. If they are rolling their eyes, you did not.

Warning Sign #4: CRM Data Quality Is Getting Worse, Not Better

What It Looks Like:

You check the CRM three months after your VP started. It is still a mess.

Deals are stuck in the same stage for weeks
Notes are incomplete or missing
Forecasting is still wildly inaccurate
Reps are not following the process

Why It Is a Red Flag:

The CRM is the operating system of your sales team. If your VP has not fixed it in 90 days, they either do not understand how to configure CRM workflows (incompetence), or do not believe CRM hygiene matters (wrong priorities). Both are fatal.

What You Should See Instead:

A great VP makes CRM optimization their first priority:

Week 1: Audit the current state and identify the problems
Week 2-4: Redesign the pipeline stages and train the team on new workflows
Week 5+: Enforce discipline through daily reviews and accountability

By Day 60, your CRM should be a source of truth, not a garbage dump.

Warning Sign #5: They Blame the Product, Not the Process

What It Looks Like:

Every time you ask why revenue is not growing, your sales VP points to external factors:

"The product is not competitive."
"Marketing is not generating enough leads."
"The market is saturated."
"Our price is too high."

They never say: "I am testing a new outbound cadence" or "I am retraining the team on discovery calls."

Why It Is a Red Flag:

Blame is the language of failure. Great leaders take ownership. Weak leaders deflect.

Yes, sometimes the product or pricing is the problem. But if your VP is blaming everything except their own execution, they are not going to fix anything.

What You Should See Instead:

A great VP says:

"Here is what is not working in our process, and here is my plan to fix it."
"I tested three different email sequences. Here are the results."
"Our discovery calls are weak. I am rewriting the script and coaching the team."

Ownership, experimentation, accountability. That is what great VPs sound like.

Warning Sign #6: No Documented Playbook After 90 Days

What It Looks Like:

You ask your sales VP: "Do we have a Sales Playbook yet?"

They say: "I am working on it" or "It is almost done" or "I am still gathering input."

It's been three months. There is no playbook.

Why It Is a Red Flag:

The Sales Playbook is the foundational deliverable for any sales leader. If it does not exist after 90 days, it means one of two things:

They do not know how to build one (they have only worked at companies where it already existed), or
They do not think it is important (they believe sales is only an art, and not a science, as well)

Either way, you are in trouble.

What You Should See Instead:

A great sales VP delivers a V1 playbook within 30-60 days. It does not need to be perfect. It needs to exist.

The playbook should include:

Ideal Customer Profile (ICP) definition
Sales stages with entry/exit criteria
Discovery call framework
Objection handling scripts
Pricing and negotiation guardrails

Version 1 is better than waiting for perfection.

Warning Sign #7: They Are Networking More Than Managing

What It Looks Like:

Your VP is on LinkedIn a lot. They are attending conferences. They are taking calls with recruiters.

They are not in pipeline reviews. They are not coaching reps. They are not closing deals.

Why It Is a Red Flag:

When a sales VP is spending more time "building their brand" than building your sales team, they have mentally checked out. They are either:

A. Positioning for their next job (because they know this one is not working), or

B. Avoiding the hard work of execution by hiding behind "strategic" activities

Either way, you are paying for their job search, not their output.

What You Should See Instead:

A great sales VP is obsessed with the team's performance:

They are in Slack constantly, answering rep questions
They review every lost deal to identify patterns
They spend evenings listening to call recordings

If your sales VP is hard to reach because they are "at a conference," that is a problem.

The Cost of Waiting: Why You Cannot Afford to Hope It Gets Better

Let's run the numbers on what happens if you wait.

The Direct Costs

Salary: $200,000/year = $16,666/month
Recruiter fee: 20-25% of first-year salary = $40,000-$50,000 (already paid, sunk cost)
Equity grant: Typically 0.5-1.5% depending on stage

If you wait six more months hoping it improves, you have spent an additional $100,000 in salary.

The Indirect Costs

But the real damage is not the salary. It is what you are NOT getting:

Lost Revenue:

Your revenue should be growing 20-30% quarter-over-quarter if you have the right sales leader. Instead, it is flat.

If you are at $4M ARR, that is $800,000 to $1.2M in lost growth over six months.

Team Attrition:

Your top rep quits because they are frustrated with the lack of direction. Replacing them costs $50,000 in recruiting and 6-9 months of ramp time (another $100,000+ in lost productivity).

Founder Burnout:

You step back into sales because your sales VP is not executing. You are back to being the bottleneck. All the CEO-level work you should be doing (fundraising, partnerships, product strategy) gets delayed.

Board Confidence:

Your board starts to question your judgment. "This is the second sales VP you have hired. Why do they keep failing?" This makes it harder to fundraise and recruit top talent.

Total Cost of Waiting Six Months:

Direct: $100,000 (salary)
Indirect: $1,000,000+ (lost revenue, attrition, opportunity cost)

Total: $1,100,000

Waiting is not patience. It is financial malpractice.

How to Salvage the Situation: The Two-Path Decision

If you are seeing 3+ warning signs, you have two options:

Option 1: Build the Infrastructure Your Sales VP Needs to Succeed

Sometimes the sales VP is salvageable. They are competent, but they have never built systems from scratch. They need scaffolding.

Solution: Bring in a Fractional Sales Leader to build the infrastructure.

The Fractional Leader does not replace the VP. We work immediately before, or alongside them for 90-120 days to:

Build the Sales Playbook they should have built
Configure the CRM workflows
Train the team on the new process
Implement weekly cadences (pipeline reviews, training sessions)

Once the infrastructure exists, the VP can do what they are good at: optimizing and scaling.

This works if:

The VP is coachable and willing to admit they need help
The team still respects them (no major trust breakdown)
The founder believes the VP has the right strategic vision, just lacks execution ability

Option 2: Replace the VP with a Fractional Sales Leader

If the VP is not salvageable (team has lost respect, they are not coachable, or they are actively destructive), cut your losses.

Solution: Fire the sales VP, bring in a Fractional Sales Leader to stabilize, then decide if you need a full-time sales VP later.

This approach:

Costs 60-70% less than keeping a failing VP
De-risks the role (if the Fractional Leader does not work out, it is easier to exit)
Buys you time to make a better hiring decision later

The Fractional Leader will:

Take over sales management immediately (no ramp time)
Build the playbook and infrastructure you should have had
Stabilize the team and restore confidence
Hire and train new reps if needed
Prepare the organization for a future full-time VP (if you need one)

Example:

One of my clients fired their VP after six months of poor performance. I came in as the Fractional Sales Leader, rebuilt the pipeline process, and trained the team. Revenue grew 40% over the next 12 months. We eventually hired a full-time Sales Manager (not a VP), and the founder now has a scalable system.

As one client said:

"Louie came in and helped bring together all our sales efforts into a system with a Sales Playbook, realistic pipeline, and defined roles. We are better off from having Louie here." — Systems Engineer - eCommerce company

The Diagnostic Framework: Should You Save or Replace?

Use this decision tree:

Save the VP if:

✅ They are coachable and admit they need help
✅ The team still respects them
✅ They have strong strategic vision (just weak on execution)
✅ The relationship with the founder is still intact

Replace the VP if:

❌ The team has lost respect (turnover is happening)
❌ They blame everyone but themselves
❌ They are defensive or resistant to feedback
❌ The founder has lost confidence in them

When in doubt, replace. The cost of keeping the wrong person is always higher than the cost of starting over.

How to Have the Conversation (If You Decide to Replace)

Firing a VP is hard. Here is how to do it professionally:

Step 1: Be Direct and Respectful

"This is not working. I do not think this is the right fit for where we are as a company. I am going to make a change."

Do not sugarcoat it. Do not make it ambiguous. Be clear.

Step 2: Offer a Generous Severance

If you can afford it, offer 2-3 months of severance. This buys goodwill and reduces legal risk.

Step 3: Transition Quickly

Do not drag it out. Once you make the decision, act within a week. Announce it to the team clearly and positively.

"We have decided to part ways with [VP Name]. I am bringing in [Fractional Sales Leader] to lead the team while we figure out our next steps."

Step 4: Rebuild Morale

Your team is watching. If you handle this poorly, they will panic.

If you handle it well ("We are investing in better infrastructure and leadership"), they will feel relieved.

Preventing This in the Future: Hire a Builder, Not a Driver

If you do hire a full-time VP in the future, use this framework to avoid another mismatch:

Question #1: "Describe a time you built a sales process from scratch."

If they talk about optimizing an existing process, they are a Driver.

If they talk about creating stage definitions, writing the first playbook, and hiring the first reps, they are a Builder.

Question #2: "What will you do in your first 90 days?"

Red flag answers:

"I will develop a comprehensive go-to-market strategy."
"I will assess the team and make recommendations."

Great answers:

"I will shadow every sales call and rewrite the scripts."
"I will audit the CRM and fix the pipeline stages."
"I will run daily standups and coach the team in real-time."

Question #3: "Have you ever worked at a company under $10M ARR?"

If the answer is no, proceed with extreme caution. They may not understand the resource constraints and scrappiness required.

You Do Not Have to Do This Alone

If you are in this situation right now — three months into a VP hire that is not working — you are not alone.

This happens to 60-70% of companies in your stage. It is not a reflection of your judgment. It is a predictable outcome of a structural mismatch.

But you cannot wait it out. The longer you delay, the more expensive this gets.

Frequently Asked Questions (FAQs)

Q: How quickly should I expect to see results from a new VP of Sales?

A: You should see process improvements within 30 days (CRM cleanup, new scripts, training sessions) and early revenue impact within 90 days (improved close rates, faster pipeline velocity). If you see nothing changing by Day 60, that is a major red flag.

Q: What if my sales VP says they need six months to "ramp up"?

A: That is a red flag. Six months is far too long. A competent sales VP should be making visible progress within 30-60 days. "Ramp time" is an excuse weak VPs use to avoid accountability.

Q: Can I demote a failing VP to a lower role instead of firing them?

A: Rarely works. Once someone has been given a sales VP title and fails, demoting them destroys their credibility with the team. It is kinder to both parties to make a clean break and offer severance.

Q: Should I tell my board that the sales VP hire is not working?

A: Yes. Be proactive, not reactive. If you wait until the board asks, you look incompetent. If you bring it up first with a clear plan (e.g., "I am bringing in a Fractional Sales Leader to build infrastructure and stabilize the team"), you look decisive.

Q: How do I avoid making this same mistake again?

A: Use a Fractional Sales Leader to build the infrastructure first. Once you have a documented playbook, a clean CRM, and a team that is hitting quota, THEN hire a full-time VP to scale what already works. Never hire a VP to build from zero again.

Take Action Now — Before It Gets Worse

If you recognized your situation in this article, do not wait another month hoping things improve.

They will not.

The warning signs do not go away. They compound.

You have two choices:

Bring in help to build the infrastructure your VP needs (if they are salvageable).
Replace them with a Fractional Sales Leader who knows how to build from zero.

Either way, act now.

Schedule a 30-minute consultation call to discuss your specific situation and get a plan.

About the Author

Louie Bernstein is a Fractional Sales Leader with 50 years of sales experience helping $1M-$10M ARR companies recover from failed VP hires and build scalable sales systems. He founded MindIQ (INC 500 company) and has helped dozens of founders navigate the painful transition from founder-led sales to professional sales leadership.

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