Part 4 of 6: Applying The Ultimate Sales Machine to a Career in Institutional Finance and Digital Assets
I’ve built and managed Sales and Business Development teams in both small FinTech companies and in hypergrowth Digital Assets companies. From low-touch, automated sales processes to sales cycles that ran 18 months and the average deal touched six decision-makers before closing. I’ve also reported to multiple VP of Sales people whose main function in life is to run a pipe crawl, and find ways to intermediate reporting processes while adding zero value to sales processes. That’s why this section from Chet Holmes’ The Ultimate Sales Machine has always been so important to me. Chet Holmes is blunt about this: most sales training doesn’t work. Not because the content is bad, but because of how it’s delivered. A two-day offsite, a motivational speaker, a new methodology rollout…. then everyone goes back to doing exactly what they were doing before. Holmes calls this the “event” model of training, and he’s right that it’s largely theater.
His alternative is simple and uncomfortable: train your team on a small number of core skills, repeatedly, forever. Not a new curriculum every quarter. The same things, drilled until they become automatic. He argues that most salespeople know what to do but they just don’t do it consistently under pressure. The gap isn’t knowledge. It’s execution. And execution is built through repetition, not revelation. This goes back to Holmes’ “pig-headed determination” characteristic he looks for in hires.
WHY THIS IS HARDER THAN IT SOUNDS
There is an assumption that smart people selling sophisticated products just need to know the material deeply enough, and the rest will follow.
It doesn’t follow. I’ve watched brilliant people who understood the product thoroughly lose deals they should have won because they couldn’t read the room, or couldn’t handle a tough objection without getting defensive, or couldn’t structure a conversation to move a skeptical CIO from interested to committed. Those are skills. They are learnable. But sales people don’t learn from a one-time workshop.
Holmes’ prescription is consistent, focused weekly training sessions. Not to introduce new concepts, but to practice the ones that matter most. Objection handling, discovery questioning, the opening of a pitch, how to follow up without being annoying. The same scenarios run over and over, until the response becomes instinctive rather than effortful. And there is a key part of these training sessions that everyone cringes at, but is ultimately powerful…role playing. Assign roles, prep skeptical questions, and then pick your sales person. Let this play out in a small group. And those not part of the role playing need to take notes as they will be asked to dissect and analyze the process as if presenting a case study in front of an 8am MBA class.
WHAT THIS LOOKS LIKE AT A DIGITAL ASSETS FIRM TODAY
The digital assets sales environment is uniquely challenging right now because you’re often selling to buyers who are simultaneously interested and skeptical. These are institutional counterparties who have board-level pressure to have a digital asset strategy but significant personal career risk if they move too early or pick the wrong partner.
That dynamic requires a specific set of skills that are different from standard enterprise sales. You need to know how to validate a buyer’s caution without letting it kill momentum. You need to know how to handle the objection “we’re watching but not ready”. This is often code for “help me find a reason to move now.” You need to be able to translate highly technical infrastructure questions into risk-adjusted business decisions that a CFO or CRO can actually act on. And you need to be able to speak with the many different departments, many of whom have zero incentive to make a change. The Operations & Admin team at a large scale asset manager are going to have many objections to creating an entirely new set of processes and associated security changes to support any form of new technology.
None of that comes from a product training deck. It comes from practicing those specific conversations, getting feedback, and doing it again. A team that runs through the “we’re watching but not ready” objection every week for three months will handle it completely differently than a team that covered it once in an onboarding session.
THE COMPETENCY HOLMES FOCUSES ON MOST
Holmes identified twelve competencies of what he calls a “master salesperson”, including rapport-building, follow-through, and the ability to handle rejection without losing momentum. The specific list matters less than the underlying principle: great salespeople have identifiable, trainable skills, not just personality traits or product knowledge.
This reframe matters because it changes how you hire, how you onboard, and how you manage. If sales performance is purely about talent and fit, you can’t do much when someone underperforms except replace them. If it’s about trainable skills, you have something to work with.
Time for an anecdote: During my time at Circle I was given a team of 8 sales people who had been hired by a former VP, who had been terminated, to sell a product that had been discontinued. In my initial interview of each of them, I asked for their thoughts on who Circle was competing with, and what we were selling. Only one of them answered my questions to my satisfaction. I then asked for each to send me 1 USDC. Again only one of them had a digital assets wallet on their mobile and could execute. After two months of weekly training in group settings and 1:1 follow ups, I had let 5 of them go. The skills and interests they had were not compatible with the rapidly evolving market for stablecoins and the ancillary services Circle was providing; they were not trainable.
In my experience, the firms that build durable sales cultures are the ones that treat training as infrastructure, not overhead. It’s not something you do when numbers are down or when a new product launches. It’s something that happens every week, regardless of what else is going on, because that consistency is exactly what separates a team that executes reliably from one that performs unpredictably.
Holmes built this insight from actually managing sales teams, not theorizing about them. That’s why it still holds. The tools have changed. The platforms have changed. Human beings under pressure in a sales conversation have not.