So You Want to Be a VP of Sales
WMMM #093 - This week, I share a perspective for early growth.
Jeff Keplar Newsletter March 29, 2025 7 min read
At a tech startup.
It's first VP of Sales.
Do the Due Diligence - Know What the Data Says
Do you know what happens to most "first VPs of Sales" at tech startups?
They fail.
They are unlikely to make it past 12 months.
Ask around.
Find as many tech startups as possible that have reached $15M ARR.
Use Crunchbase or Pitchbook.
Identify the VPs of Sales.
How many predecessors do you find?
Now contemplate that for every startup that reaches $15M ARR, there are conservatively 50 that don't get there.
And many of those have hired at least one VP of Sales that failed.
Shame Shame
This is a shame because it can be so harmful for the startup.
It can cause such a loss in momentum.
It can cause doubt and confusion among the other employees.
It wastes precious time:
Time for competitors to catch up to any first-mover advantages it possessed
Time which delays the ability to advance past the initial traction phase.
Doubt creeps into the customer base.
Investors get antsy.
Time burns its precious capital:
Running out of money is the #1 cause of startup failures.
Why Do They Fail?
One reason the first VP of Sales fails is that the job is extremely difficult.
Another is the incorrect expectations of what they need to do.
Sometimes, the VP of Sales is hired too early.
Other times, the founder/CEO makes the wrong hire - they aren't looking in the right place or for the right skills.
In many cases, the person hired is missing skill(s) and doesn't have help to fill their gaps.
It's become popular to "copy and paste" from successful startups.
Many startups are advised that there is a cookie-cutter, rinse-and-repeat easy button for scaling sales.
Talent decisions are made from LinkedIn profiles or resumes.
When I see this, I suspect it's because those providing the advice or making the hiring decisions don't trust their ability to evaluate the candidate.
They may not know what to look for.
For such a difficult hire for such a crucial role, founder/CEOs could benefit from advice from someone with deep domain expertise in first-line sales management with enterprise sales teams.
I want to help by providing a perspective.
What should a good VP of Sales not be doing?
The VP of Sales should not be the first salesperson for the startup.
They may have been, and possibly still are, good at selling.
However, if they possess the recent sales leadership experience required for this role, they likely have not been an individual contributor for quite some time.
They have progressed to the next level, where they are "force multipliers."
They generate more revenue with the same or less effort.
They do this by making the sales reps they work with better at selling.
Their strength is no longer that of an individual contributor.
Their strengths in a sales cycle are now playing the role assigned to them by the sales rep in a "team selling" approach.
Their role is a bit part, requiring a fraction of their time.
In comparison, the sales reps invest an order of magnitude more time running the sales cycles.
Teaching the "team selling" approach is also a strength the sales leader possesses.
There are better answers for the need for the first sales rep than hiring a VP of Sales.
Ideally, the CEO/Founder has hired a couple of experienced startup sales reps to help them win the first 5-10 customers.
This phase is known as the Friends and Family approach.
There is no outbound (lead generation) system.
The founder, the Board of Directors, and investors source their networks for leads.
The experienced startup reps work these leads.
They are also skilled at lead generation and may have a personal outbound system to assist them.
I'll share the profile for these experienced enterprise sellers later.
This approach helps the startup establish a product-market fit.
As it approaches ten customers, it is building momentum.
The startup is ready to begin to scale.
Enter the VP of Sales with the following priorities.
1-Refine the Ideal Customer Profile and target market segment.
What was learned from the pursuit and implementation of the first ten clients?
What are the use cases?
What patterns appear?
How can they be applied to the larger market?
2- Capture the story the Founder/CEO tells about the vision that created the company.
Early clients have relied on this story, and to scale, it has to be communicated about the founder by others, not exclusively by the founder in sales cycles.
3-Recruit the best reps for selling into the target market.
Delivering revenue at this stage requires sales headcount.
You need leads.
And you need to convert them.
This can't be done with a founder and a couple of techs.
It can't be done with only a VP of Sales and a pre-sales resource.
You need a sales team.
And, once they have 4-6 reps, the best don't stop.
They keep recruiting.
Even with zero attrition, you have to have a path to your next 2-3 reps.
This task isn't easy, adding to the degree of difficulty for the VP of Sales.
The best reps are typically successful where they are.
They are making money.
They know that any time a salesperson makes a job change, it costs them money in the near term.
They must invest in the new firm to build a pipeline.
They will evaluate the lead generation system in place and the size of the funnel they have to work with.
They will evaluate the incentive compensation plan and their ability to make more than they do today.
Depending on the sales cycle length, it will take at least 3-6 months before they are making sales.
4-Build an Outbound System
No lead generation system?
The best reps are comparing our startup against their current environment and other startups.
They are assessing their ability to make money.
So, the VP of Sales has to build an outbound system to attract the best talent.
They should plan on doing so simultaneously with recruiting the best talent.
For clarity, the founder posting on LinkedIn or speaking at industry conferences is not an outbound system.
Software like Apollo.io, SalesLoft, and Hubspot facilitate a repeatable, scalable outbound system.
Who creates the leads?
What is the role of the sales rep in this area?
Are they performing the cold calling, sending emails, and prospecting on LinkedIn?
Conventional wisdom has concluded that hiring experienced sales pros will have a better ROI if you use a less experienced resource to generate leads.
The VP of Sales must build a team of business development reps (BDRs.)
Unless that VP of Sales has experience with this part of the business, they will likely hire a BDR Manager to build this team and the Outbound system.
As it is with most "wisdom," there are exceptions.
The one that comes to mind is when the target market is tiny, accompanied by a lengthy average sales cycle time, and a 7-figure-plus average deal size.
For example, the best market for what you sell is the six U.S. financial institutions classified as TBTF (too big to fail.)
In this case, an experienced enterprise sales rep with domain expertise in banking is a better choice for their own lead generation.
Of course, they must be trained in the skills required to perform outbound.
Most experienced sales candidates in larger organizations have had BDRs doing the outbound.
If they need outbound skills, this reduces the size of the candidate pool.
However, for most situations, having BDRs to create leads and experienced sales reps to qualify and run the sales cycles is optimal.
When working in the same territory, the BDR and sales rep will form a tight team.
For this reason, it is best to plan to match the number of BDRs with the number of sales heads.
In order to get the best to leave where they are, the VP of Sales has to possess their trust.
This can only happen when there are many of these successful reps who have worked with the VP of Sales and trust them as a leader they want to follow.
More on this when I share the hiring profile for the VP of Sales later.
5-Help the Team Sell
I've frequently heard it said that the VP of Sales's role is to close deals.
I do not agree.
Especially in the enterprise space.
When done properly, it doesn't work that way.
"The Close" is anticlimactic - merely the end of a carefully choreographed process.
The role is to use their experience to make each individual better.
It's observing each rep and noting what they do well and areas they can improve.
It's communicating the positive behaviors witnessed.
It's about leading by example.
This helps instill confidence and trust.
It's about coaching them in the areas where they can do better.
These are tasks that happen daily.
They are constant and never-ending.
A good VP of Sales can see around corners, reducing errors and improving execution.
6-Capture Data and Communicate
When the entire company depends on one department's success, communicating results is important.
To enable this, the VP of Sales must implement processes that capture data and facilitate timely and accurate communication of the business.
Sales is like oxygen for a startup.
In that regard, the role of the VP of Sales is to do whatever it takes to get revenue in the door.
Headcount costs the startup precious operating capital.
Sales reps, BDRs, and the VP of Sales cost money.
The quicker it can cover those costs with a predictable revenue stream, the better.
But that does not mean that the role of the VP of Sales is to open doors, create opportunities, and close business themselves.
I intentionally left this off of the VP of Sales' priorities.
They won't create enough sales quickly enough.
They have to be force multipliers.
It's like applying the wrong tool for the job.
This is a common reason that the first VPs of Sales fail.
It is one of the reasons that startups fail so frequently.
It's okay to try and fail.
That's how we learn.
A smooth sea never made a skilled sailor.
"Success is a lousy teacher.
It seduces smart people into thinking they can't lose."
Bill Gates
But isn't it preferable to learn from others' failures?
"Those who do not learn history are doomed to repeat it."
In next week's edition, I'll discuss the hiring profiles for the experienced startup sales rep and the first VP of Sales.
Lessons Learned
1) Don't hire our VP of Sales to be our first sales rep.
2) Don't hire our VP of Sales too early.
3) Founder/CEOs could benefit with help from those with deep sales leadership expertise.
4) There isn't an "easy button" recipe for scaling sales.
5) With so much failure, there are plenty of examples of what not to do.
Thank you for reading,
Jeff
When you think “sales leader,” I hope you think of me.
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