Drop Everything Now…
WMMM #094 - This week, I share my observations for solving that early stage failure rate.
Jeff Keplar Newsletter April 19, 2025 10 min read
…and read this if you are hiring your first VP of Sales,
or if you want to be that VP of Sales.
Previously
In So You Want to Be a VP of Sales, we observed the failure frequency for a startup tech company's first VP of Sales.
This may be because they were hired too early.
Hiring managers had incorrect expectations for the role.
They weren't looking in the right places or for the right skills.
Decisions were made from LinkedIn profiles or resumes.
And it's a tough job.
There is no "easy button" for this challenge.
I offer my observations to help those leaders of startup tech companies and those would-be VPs of Sales.
Why not start with a couple of experienced enterprise tech sales reps before hiring that VP?
Use the Friends and Family approach to open doors.
Win your first five clients.
Establish product-market fit.
Then, hire the first two sales reps to help us get the next ten.
At that point, you are in a better position to utilize the skills of a VP of Sales and receive a much higher value from that hire.
I promised tips for hiring that VP of Sales in this edition.
I also prepared the profile for those first two sales reps.
But when proofing the newsletter, the reading time for this edition jumped to over 14 minutes.
I have learned my lesson about long newsletters.
Once bitten, twice shy.
Check out next week's edition for profiles on the two senior reps to start your sales org
For this week, I focus on selecting the VP of Sales.
That First VP of Sales
The ARR run rate after reaching ten customers should exceed $2M.
When the startup reaches 20 customers, their ARR should be at least $5M.
At some point between 10 and 20 clients, the startup can begin thinking about hiring a VP of Sales to scale the business.
This will involve hiring reps for direct sales and BDRs for outbound (leads.)
Most enterprise tech companies need pre-sales resources to pair with direct sales reps.
Add that to their list.
If a marketing department hasn't been built, now is the time for that too.
Marketing drives awareness and inbound traffic (leads.)
This task is often assigned to the VP of Sales.
Many also look to indirect channels to become Force Multipliers.
Add building an Alliances team to the VP of Sales duties.
Most enterprises consult industry analysts like Gartner and Forrester.
The VP of Sales will have to take on that role unless a Product Manager can, or they hire a resource for the analyst community.
The founder can't be everywhere.
The VP of Sales becomes the 2nd face of the company for industry conferences and social media interviews.
Progress with business development and updates on revenue growth are an important part of the job.
The VP of Sales must implement data-gathering systems to help them accurately track and report sales progress.
This role is much more than one person can do.
At scale, a mature sales organization will have a different person leading a team for each of these requirements.
Not so with a startup.
It is one person for the time being.
When is there time for "coaching up" each individual sales rep?
Are these sales reps immune from the need for motivation, skills development, role-playing, another set of eyes on the complex politics of an enterprise, qualification, critical thinking, storytelling, and active listening?
Of course they aren’t.
They are less effective without it.
What About The Founder?
Previously, in So You Want to Be a VP of Sales, we discussed the priorities for this role.
Additionally, we introduced the need for Force Multipliers.
Anything that helps us do more with the same or less effort.
An obvious Force Multiplier is more sales reps - a sales force.
Adding 4 performing heads to our 2 vets amplifies their effectiveness.
Automation tools like Hubspot and Apollo.io assist with outreach, follow-up, and lead scoring, reducing time spent on administrative tasks.
A well-defined sales process, an effective onboarding program, and skills development improve conversion rates, reduce sales cycle length, and increase average deal size.
Skilled reps close more deals with larger orders.
Most CEO/founders have never carried a bag.
That doesn't mean they can't sell.
They help convince investors when raising capital.
Their vision for creating the startup is intoxicating to early customers.
That's selling, right?
Yes, but…
Those early clients are traditionally friends and family.
That's a one-time proposition.
Sharing their vision in a sales cycle that a senior sales rep runs is but one out of hundreds of actions, reactions, and decisions in that sales cycle.
Penetrating an enterprise account without the help of relatives is a whole different proposition.
Doing it over and over again with a quota hanging over your head is not even in the same zip code.
Successfully achieving a quota in the enterprise tech space is much different than getting those first 5 clients.
Sales skills are required for both, but they are not the same.
Accomplishing one does not mean you can do the other.
And neither are the same as what is required of that first VP of Sales.
I've gone out of my way to set up this critical observation.
Should the CEO/founder run sales if the objective is to scale out a direct sales force?
Many think they could if they could only clone themselves.
Is it reasonable to think they could do both jobs if given enough time?
Could this contribute to the errors made when hiring the first VP of Sales?
How could they know what the role requires or what it takes to perform it?
Could this cause them to look in the wrong places for the wrong things?
Don't they also receive advice from others?
Do they understand enough about the challenges to discern bad advice from good advice?
Besides, the CEO/founder's time is better spent on other requirements.
Many of these have a direct impact on the viability of the company.
A situation requiring the founder's immediate attention can present itself at any time on any day.
Some of these situations pose a significant risk to the startup's existence.
For example, a piece of product functionality isn't operating correctly under a particular set of conditions.
What if the founder architected this area in the system?
They are the best resource for determining the resolution.
Fixing a single line of code to remedy the problem is not always the best approach.
How does this change affect the hundreds of other conditions this code might encounter?
Does this compromise the architecture?
It could take the founder's undivided attention for hours.
They may have to pour through lines of code to recollect how they designed this area and why.
It may require thinking through the architecture to determine if this bug could reappear in another scenario.
It could take over a week to resolve this problem
This activity could be more critical to the company's future than anything else requiring the founder's time.
And this is only one example of dozens.
Meanwhile, a sales cycle can have hundreds of moments requiring the sales reps' attention.
Many of these are mundane, grind-it-out tasks requiring perseverance.
Some turn out to be one of those key moments where the correct action or response is key to winning.
Conversely, the wrong response could cause a loss.
To make matters worse, the sales rep can't just parachute in for one of those key moments.
They have to be the person who is also dealing with the hundreds of other moments.
Why?
Perspective.
It often requires context and perspective from multiple "moments" to make the right call - the appropriate response - for that key moment.
In either case, these moments in a sales cycle pose little risk to the startup's existence.
So, where should the founder be focused?
(Not on running a sales team or sales cycles.)
Where Do We Look and What Are We Looking For?
Successful Exits?
It is popular to copy and paste from those that made it.
This includes company strategy, processes, and people.
Many investors will advise their portfolio founders that they will place a VP of Sales from a company in their portfolio that had a successful exit (a monetization event) into the same role in their startup.
They have just reduced the risk in their minds.
Since this individual was with that company when it monetized, they must have what it takes and will replicate their success with this founder, right?
Really?
I'm serious when I share that, in many cases, the process doesn't go much deeper than that.
I once spoke with a partner in a private equity firm about this very topic.
He told me that he had been one of those that was placed in a VP of sales job.
His startup had been acquired by Oracle.
He told me that the VC firm would not consider anyone for that role that had not been part of a successful exit.
He also highlighted the flaws with that approach and provided example after example of where it had gone wrong.
He was authentic, the real deal.
I learned a lot from my conversation with him.
Taking this easy way out is a common bias.
Psychologists call this the halo effect.
It's a cognitive bias that elicits a shortcut to a decision in the human brain.
When we see something good in one area, we assume excellence in others, even when no evidence exists.
This bias is a rudimentary concept in influencing decisions, yet here it is.
I have observed many talented sales leaders experience a successful exit.
Many would be excellent candidates for that next startup's VP of Sales position.
But not solely because they held that role at the moment of monetization at another startup.
I have encountered just as many that would not be good candidates.
Here are some thoughts that might help us prevent the halo effect from making a bad decision.
How long did it take from winning the first client to a successful exit?
When did our candidate join the startup, and how long were they there?
I know a few examples where that sales leader joined just 6 months prior to the exit.
After 8 years of customer acquisition with a direct sales organization built by someone else, how much impact could they possibly have had?
To be fair, they may have provided a perspective in that short stay that made a difference in the monetization event.
Uncovering that requires several layers of questions by someone intimate with the role of a VP of Sales.
But, until we have the results from those layers of questions, the person joining as the VP of Sales in the final year prior to a successful exit was the beneficiary of timing.
It is highly unlikely that their actions led to the monetization event.
Put a dent in that halo.
Don't Do This and Don't Do That
At this point, all I am offering is what not to do.
Knowing what not to do is sometimes more than half the battle.
It will save you from wasting time.
Another "not" is looking for a title with “VP.”
Does anyone fact-check what people put in their LinkedIn profiles?
No.
How about their resumes?
I'd eliminate LinkedIn profiles and resumes from your decision process.
LinkedIn comes in handy for other reasons, which I highlight later.
The VP title is not a requirement.
What they or their employer call them is less important than their verifiable behaviors while performing their job.
Sales Manager, Sales Director, Regional Manager, and Regional Director are all okay.
A first-line sales manager is the most challenging job in a sales organization by a longshot.
I won't go into detail about why here, but anyone who has worked in the profession knows this to be true.
A candidate must be a current or former first-line sales manager.
If they were promoted to a mid-level sales management position that may be even better.
They have managed sales managers.
We are looking for coaching sales managers who are also coachable.
Do they know what "good" looks like at scale?
Any higher in a large sales organization, for example, an Executive Vice President, and I would use caution.
There can be ideal candidates in those executive positions, but the job to be done in the startup is far from what those individuals do today.
Another way of saying this is that it's been a long time since those folks did what the startup needs to do right now.
Get in Position to “See” your next Leader
Have you ever heard the saying that it's hard to describe, but we know when we see it?
Say you want to find someone that is considerate of others.
Someone who thinks of others in every facet of their life.
It's not a conscious effort.
They do it as a habit.
How would you prescribe how one would go about finding such a person?
But what if you asked an acquaintance of theirs if they were considerate?
The acquaintance tells you the story of when they lent this person their truck.
The tank was only half full of gas, but that was okay because they weren't going very far.
And when that person returned the truck, the gas tank was full, and there was a 6-pack of their favorite Shiner Bock in the front seat.
We know it when we see it.
Look For Someone Like This
For the first VP of Sales at an enterprise tech startup, here are some observations for finding those who can do the job.
First, we will need help finding these folks, so seek help.
Look for former sales leaders and recruiters now in business to advise startups.
They will find a group of suspects.
The suspects will have sales management experience.
Preferably, they have received professional training in sales, coaching, and leadership.
They are coachable.
They have a decade's worth of experience and a track record of success.
Once we have a list, find the individual contributors that have worked for them.
(LinkedIn is a good tool for doing this.)
These people are a much better source of data than the suspect's superiors.
Here are some suggested questions.
What did you learn from them while working together?
Did your sales skills improve?
Did your results improve?
Did they care about your success?
How do you know?
When they hired new people, what were the results?
Who would you take if you had an opportunity to take someone on a sales call with you?
Why or why not them?
Do you consider them a coach?
Did you feel your job was more rewarding or less when they were around?
Did they make things easier, in general?
Did you change your behavior as a result of something you saw them do or heard them say?
Did they have a playbook for you and their team?
What about a process?
What kinds of questions did they ask during deal reviews?
How often did you interact with them on a weekly basis?
Would you work for them again?
These questions should generate enough discussion to create many follow-up questions, doubling what I have shared here.
The more time we spend speaking with the sales reps who worked with a sales manager, the better the chance we will identify our next sales leader.
No one promised this was easy.
But it is positively doable.
We might ask ourselves: Why do we frequently see startups approaching the problem in the very way that I advise against?
That is a fair question.
How is that working out for them?
See "Most first VPs of Sales fail" in: So You Want to Be a VP of Sales.
It takes courage to try something different.
The odds are that by continuing to do as the others do, the startup is doomed to fail with its hire of a VP of Sales.
I have offered my observations for why this happens in an effort to help.
There is no sure thing with a challenge like this one.
Based on my experience, using a different approach is reasonable and logical.
Different Approach = This approach.
We must first admit to ourselves that we must change and need help to do so.
Lessons Learned
1) Resist the halo effect - CEO/founders should get help to identify the right VP of Sales.
2) With the overwhelming evidence, breaking from the current approach isn’t as risky as we might think.
3) The most reliable information comes from those who worked for the candidate - invest your time with them.
Thank you for reading,
Jeff
When you think “sales leader,” I hope you think of me.
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I offer my help to investors, founders, sales leaders, and their teams.
I possess the skills identified in this article and share them as part of my service.
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