Talent Goes Where Talent Wants
WMMM #099 - This week, I share more lessons from the outstanding sales leaders in my career.
Jeff Keplar Newsletter May 31, 2025 3 min read
We were in a growth phase, and our segment of the industry was highly competitive, with multiple well-funded entrants.
The market was ever-changing, with a new “capability” becoming table stakes for each entrant seemingly every ninety days.
Hey, those of us selling AI or cybersecurity today: Does this sound familiar?
We Aren’t Always Going to Have “It”
While we had some significant technical advantages in our Product, there is no way we could always be first and best with each new feature every quarter.
If our sales strategy relies on product superiority, there will always be a new capability—a feature or API—that a competitor will have before us.
Moreover, it is unknown and unpredictable how long it might be before we catch up.
How long will it be until we have “it,” whatever “it” is?
It doesn’t matter how inconsequential in the overall value proposition “it” may be.
We don’t have it.
“Talent Goes Where Talent Wants” was spoken in the context of building a great sales team.
An excellent leader was speaking at a company event.
Most of the Company was in the audience.
Our leader knew what others might not.
We cannot rely on product superiority to win business.
It is not sustainable.
There are a lot of smart folks out there, and innovation is occurring at an increasingly rapid pace.
We can enjoy product superiority one minute and find ourselves temporarily behind the next.
Time for the Sales Team to Step Up
No matter how good our engineering team is, there are few options available to us to avoid this phenomenon.
A world-class sales organization is one of them.
It can overcome a temporary gap in features and functions.
It knows how to turn a weakness into a strength.
It understands competitive positioning.
It recognizes that with all enterprise software decisions, multiple stakeholders are involved.
There is always a “game within the game.”
Our leader knew this and was making a point as he spoke to the Company.
Product releases between industry leaders, causing perceived technical leadership to ping-pong back and forth, is a common occurrence.
He was not about to allow this to prevent the Company from meeting its revenue objectives.
He would not allow Engineering to absorb one ounce of the responsibility that rightfully falls with Sales.
“We never lose to demo.”
He had excelled during one of the most competitive periods in the history of the enterprise software industry.
That period included entrants such as SAP, Peoplesoft, Oracle, Siebel Systems, and JD Edwards.
The stakes were high.
Most deals involved multi-million dollar commitments.
Each competitor had certain features that evaluators found differentiating.
Our leader led an organization whose Product’s strength was its architecture, and its perceived weakness was the user interface (UI).
He famously came up with “we never lose to demo” as a mantra.
If his weakness was UI, why would he allow his sales organization to make a product demo meaningful to the buyer’s decision process?
At the same time, he eliminated the win/loss responsibility from the pre-sales team and placed it squarely on the sales team.
It was brilliant.
It was classic sales leadership.
He knew he was asking the sales team to find a way to win.
Compete with the odds stacked against them.
Fight with one arm tied behind their backs.
But isn’t that the expectation of professional salespeople?
The best always find a way.
Others learn from the best.
The rest wash out of sales eventually.
Our leader’s sales team learned to develop a strategy to win that did not rely on the Product UI.
The rest of the story is now enterprise software history.
What Does Talent Want?
“Talent Goes Where Talent Wants” begs the question: “Where does talent ‘want’ to go?”
And the answer is the point our leader was making.
Talent wants to go where their skills make a difference.
They want to go where their contributions are recognized.
They want to work for someone who understands and appreciates what they do.
They want to work where they can be their best.
They want to work for a leader.
They want to make money.
They want to go where they can have a multi-year run.
Our leader’s message was that the Company needed to continue to up its game in order to attract and keep sales talent.
Lessons Learned
1) The value of having an excellent sales team.
2) Attracting and keeping sales talent.
3) Be worthy of being considered “talent.”
4) The best always find a way to win.
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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