Introducing the Star of the Show…
WMMM #095 - This week, I share a vital skill in team selling.
Jeff Keplar Newsletter April 26, 2025 8 min read
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.
What if we delayed that hire?
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.
Those First Two Reps
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.
First, we will need help finding these folks, so seek help.
Look for former sales leaders and recruiters who are now in business to advise startups.
They will find a group of suspects.
The suspects will have over a decade of experience and a track record of success.
I have worked with enough of them to develop a profile combining my observations for each.
In other words, there may not be one person that fits all of my observations.
These are people who have routinely exceeded their quota throughout their careers.
They have earned considerable commissions doing so.
While not independently wealthy, they are not dependent on a paycheck.
It is common to find a blip in their careers where they try something different, like starting a business or purchasing and running one.
They are confident in their ability to succeed and are willing to work at an early-stage startup because they want the highest financial leverage for the investment of their time.
The startup will need to pay more than the industry norm to employ these types.
Commission rates may exceed 3X of those norms.
In my experience, they are worth it.
Getting the first ten clients outside the friends and family circle is tough and extremely valuable to the startup.
Because of their skills, track record, and accumulated wealth, they are sometimes difficult to manage.
They have little patience for anything that gets in the way of them doing their job.
They can do their own product demonstrations.
They have a network of pre-sales technical professionals who would be great candidates as this startup grows.
They will write the script for BDRs to use in outbound efforts to get them leads.
They can do their own outbound - not depend on qualified leads for their success.
They develop competitive positioning strategies.
They will help the CEO/founder develop answers to "Why Buy Anything?" and "Why Buy from Us?"
They will quickly define the Ideal Customer Profile.
They will know the persona in the enterprise who cares about the problem their product solves.
They engage in conversations at multiple levels in an enterprise.
They learn the areas of PAIN, even if it wanders far from the solution they are paid to sell.
They will find the area in the enterprise where there is a need it is willing to spend money to resolve.
They are problem-solvers.
Early-stage software is often not an exact fit for a problem in the market.
This does not bother these reps.
They are able to sell a consulting engagement, if need be, that will deliver an improved product (for the customer and the startup) as an outcome.
They are typically good storytellers.
They know how an enterprise buys.
They are stalwart customer advocates.
They are typically outspoken.
They are great teammates and ideal resources for the next 4-6 reps hired.
They are loyal to those who show them respect and understand and appreciate what they do.
It is not uncommon to find them in pairs.
Theirs is a small world, and they enjoy working with those with matching skills.
They also know that their success rate is higher if there is another like them performing the same role at the same time.
We will need help to find them.
Most professionals who understand this subject know a few of these sales vets.
Once we know a few, we can find more.
They have extensive networks to tap into, so it becomes a small world.
Combining networks enables us to find enough candidates to fill two slots.
It isn't easy, but it's doable.
Care and Feeding
A 4-year run with these two is considered a success by both parties.
These reps typically receive their fully vested stock options by that fourth year.
With industry-average base salaries and highly leveraged commission plans, the startup is unlikely to feel the need to continue to pay that rate for new sales after they have more than 40 clients.
It will be watching its customer acquisition cost (CAC).
It will have a VP of Sales in place by that time.
It will have grown the sales organization, and the industry norms will be the playbook.
It is not an accident that I have omitted training in a particular sales methodology.
With these two, we are above a level where discussing a sales process is meaningful.
However, they know the value of having and using a sales process and do so.
(Sales skills training should come with hiring a VP of sales and scaling the distribution channel.)
This strategy works much better if these two work with ("report to") someone they respect.
Someone who understands what is communicated here.
Since hiring these two is preferable when beginning a sales organization, they typically report to the CEO/founder.
At this stage the founder is involved in the pursuit of every new customer.
They are working side-by-side with the veteran reps to win clients.
They witness first-hand how these reps approach their business.
It is common for the CEO/founder to become enamored with this type of rep,
This can set the CEO/founder's standards too high for subsequent sales hires.
It is just as common to see a conflict between these veteran reps and the CEO/founder.
They are no-nonsense types with egos likely to clash with a strong tech founder over matters of sales strategy and product feedback from early clients.
One way to solve this is for the investors or CEO/founder to bring in a "buffer."
Insert someone between these reps and the founder.
This is a temporary solution to a temporary problem.
The buffer provides advice to the CEO/founder and investors and manages/coaches the two veteran reps.
Depending on the timing, the startup could choose to find that buffer first and add recruiting the first two reps to their duties.
With this approach, the CEO/founder receives a confidant.
The two sales vets get an experienced sales leader to buffer most of the administration and "noise," enabling them to operate optimally.
We have avoided a potential problem at a critical time with a simple but uncommon move.
The Star of the Show
A vital skill of these sales vets is creating and delivering the talk track that introduces the startup founder.
The CEO/founder is the star of the show.
The objective is to positively influence the prospect's emotion(s) toward your startup.
If you were a sports fan in the 1990s, this may be familiar to you:
“From North Carolina…at guard…number 23…MICHAEL JORDAN!"
Those words are not the secret; the delivery is.
Using a specific, dramatic, long rising inflection, they were punctuated with a powerful, emphatic crescendo.
Do you remember the announcer's name?
It doesn't matter if you do.
The star of the show was Michael Jordan.
Yet, the announcer's introduction, lasting only 15 seconds, was electric.
The way he built suspense before saying Jordan's name sent the stadium crowd into a frenzy.
That Chicago Bulls PA announcer's name was Ray Clay.
What about: "Heeere's Johnny!"?
This one's iconic.
Does it need an explanation?
For thirty years spanning the 1960s, 70s, and 80s, Ed McMahon uttered one of the most legendary introductions in television history.
It was booming, joyful simplicity, filling a studio and national television audience with anticipation for what they were about to experience.
The star, of course, was comedian Johnny Carson, pioneer and king of late-night television.
I saved arguably the best for last as it relates to influencing emotions.
It is the ninth inning of a home game for the San Diego Padres, a Major League Baseball team.
It's a close game.
The Padres hold a lead over the visiting team of no more than three runs.
The stadium lights dim.
The opening bell tolls from AC/DC's "Hells Bells" echo around the ballpark.
In a heavy, serious tone, barely audible over the music, the Padre's PA announcer calls out:
"Now entering the game for the Padres…number 51…Trevor Hoffman!"
The music does most of the intimidation work.
The bell tolls and rising guitar riffs build the crowd's energy.
Hoffman enters the field from the bullpen and jogs to the pitcher's mound.
It created one of the most legendary and theatrical entrances in baseball history.
A funeral march for opposing teams.
Hoffman's entrance meant church for the visitors.
The announcer's name was Frank Anthony.
Laying The Foundation
How the information is presented - the delivery - changes how we interpret it.
For example, the star is our CEO/founder.
They have been remarkable since their youth.
Their accomplishments in school rank in the top 0.5%.
They have made a brilliant transition from academia to the business world.
They possess a specific vision for how technology can solve a current business problem that leapfrogs today's state-of-the-art.
Our prospective customer could learn about our founder through researching public data.
But without an introduction, specifically, someone to lay the foundation (LTF) in advance, our prospect's first encounter with the star of our startup might go like this:
(Founders, forgive the unfair characterization. It is necessary to make a point that you know all too well.)
Hi, I'm the founder.
Our stuff solves this, that, and the other.
But we don't have "the other."
Oh, but you will, and if you don't have our stuff, all of these bad things will happen to you.
How do you know that?
Because I'm an expert in X, Y, and Z.
I advise heads to state worldwide in X, Y, and Z.
How are you able to do that?
I have advanced degrees from Harvard and Stanford.
I sit on the Boards of ABC and DEF companies.
I wrote the code that brought the Apollo 13 astronauts back home.
I was valedictorian at my high school and captain of the swim team.
I was the lead in both Annie and Wicked on Broadway before pivoting to software.
Wow, that's impressive. What do you do with your spare time?
I'm an organ donor.
I volunteer in a soup kitchen every Sunday evening.
I'm an NFL season ticket holder, but I give my tickets to military veterans.
I, I, I.
Me, me, me.
Does that sound a little self-serving?
We call that virtue-signaling now.
Even if all of that was 100% true, delivering the content in this manner doesn't elicit the positive emotions we want.
Shame on any salesperson if they put the star of the show in a position where they have to credential themselves.
Those two experienced sales vets would never allow this to happen.
They are great at building up others.
One of their strongest points is positioning the star of the show.
Laying the foundation before the prospect ever encounters the founder.
They combine the theater, the choice of words, the voice inflection, the hypnotic subtlety, and the enthusiasm of Frank Anthony, Ray Clay, and Ed McMahon.
They provide an element of credibility and trust themselves, which only adds to the buildup.
LTF is based on Science
How information is presented changes how we interpret it. (The Framing Effect)
Social Proof: When we see others endorsing or speaking highly of someone, we are more likely to believe that person is valuable or talented simply because others seem to think so.
The trustworthiness and expertise of the person delivering the information strongly influence how believable and positive the information seems. (Source Credibility Effect)
Authority Bias: We tend to attribute greater accuracy and value to the opinion of an authority figure - even if we know little about the subject ourselves.
Lessons Learned
1) The star of any startup is the CEO/founder.
2) Do not put the star in a position of credentialing themselves for a client.
3) The first sales hires - highly experienced reps - are very good at laying the foundation.
4) There is something to be learned from Trevor Hoffman's entrance into a baseball game.
Thank you for reading,
Jeff
When you think “sales leader,” I hope you think of me.
If you like what you read, please share this with a friend.
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.
In my weekly newsletter, Win More, Make More, I provide tips, techniques, best practices, and real-life stories to help you improve your craft.
