Sam Jacobs has spent most of his career inside the machinery that turns an early-stage company into an actual business.
He led revenue organizations across B2B technology, founded Pavilion for go-to-market leaders, co-hosts the Topline podcast, and wrote Kind Folks Finish First. His work sits at the intersection of sales, company building, and the increasingly complicated bargain between operators and owners.
I knew Pavilion before I knew Sam. I was part of the community when I was still in tech, and I saw the value of having peers who understood a job that gets less secure as the title gets more senior. That problem is only becoming more relevant as AI makes work faster, noisier, and less personal.
This conversation started with sales compensation, but it became a much more useful discussion about time horizons. What should you do if you want to maximize cash over five years? What changes if you are willing to think in 20-year increments? And when does a great income become the thing that makes it harder to leave?
Here are the parts worth your time.
The operator can create the value and still miss the upside
Sam built Pavilion around a problem revenue leaders know well: the average CRO tenure at a fast-growing technology company is roughly 18 months, according to the range he sees in the market.
That matters because the most valuable part of the job often happens early. A company doing $500,000 or $1 million in recurring revenue may still be closer to a project than a durable business. The operator who helps take it to $10 million is building repeatability, installing systems, and removing existential risk.
Sam's rough math was that the one-to-ten journey can create $50 million to $100 million of enterprise value. The executive doing that work may receive around 1% of the company, then leave well before liquidity. Even if the option grant looks valuable on paper, dilution, exercise costs, and a tax bill can turn ownership into a very expensive bet on an asset the employee cannot sell.
That is the disconnect: the builder can materially de-risk the company and still be gone when the asset finally trades.
There is no new math for AI
The market can assign radically different prices to businesses that look similar on an operating basis. An AI narrative may attract a premium while a slower-growth software company is treated as if it has little value.
Sam's answer was blunt: there is no old math and new math. There is just math.
A company still needs to acquire customers profitably, serve them at a good margin, and retain them. The multiple may change. The voting machine may become unusually enthusiastic. But the operating requirements do not disappear because the product has an AI label.
I would add the financing point. A company's balance-sheet strategy is part of the business strategy. A founder with outside investors pushing for speed has a different set of options than a bootstrapped owner who can grow more slowly and keep control. Two companies with similar products can make very different decisions because the ownership underneath them is different.
High income becomes a cost basis
If the goal is to maximize cash over the next five years, Sam's advice was straightforward: join one of the fastest-growing companies, stay close to the sale, and become one of the top enterprise reps.
The harder part begins after the income arrives.
Salespeople can move from ordinary earnings to $300,000, $500,000, or more remarkably quickly. Then the apartment improves. The vacations get better. Private school, a second home, clubs, help at home, and an expensive social circle all begin to feel normal. The break-even point rises with the W-2.
I lived a version of the other path. My income climbed quickly in sales, but I kept my lifestyle closer to the lower number and invested the difference. Replacing $100,000 of annual spending is a very different problem from replacing $500,000. The lower fixed cost gave me room to leave corporate work and build something else.
The number on the compensation statement matters. The number your life requires matters more.
A lump sum changes behavior in a way salary rarely does
Sam made a useful distinction about equity. The advantage is not that equity is morally superior to cash, or that every startup option grant is secretly valuable. Most are uncertain, illiquid, and structurally difficult for employees to hold.
The advantage is the shape of the payoff.
If someone lives on a $300,000 income and receives $10 million in one transaction, the asset base is disproportionate to the lifestyle built around it. That gap creates room for compounding. Salary usually works the other way: as recurring income rises, recurring consumption finds it.
Sam applied the same logic to commissions. If a seller can live on the base salary and treat a large annual commission as capital rather than spending money, the payment begins to resemble a small liquidity event. It is not the same tax treatment and it is not guaranteed, but the behavioral mechanism is similar.
The point is not to wait a year for money if the company may not pay. The point is to create distance between what comes in and what your life automatically consumes.
The ownership equation changes with the clock
For a five-year plan, cash can be rational. For a 20-year plan, Sam would rather own the asset.
His cleanest example was simple: 1% of a $100 million company is $1 million. Owning 80% of a $5 million business is $4 million. Building the smaller company may still be hard, but the ownership math is easier to understand and the owner controls more of the outcome.
That does not mean everybody should quit and become a founder. Sam explicitly qualified it. Entrepreneurship comes with years when the corporate job would have paid more, and the operator has to tolerate being bad at a new craft long enough to learn it.
But the lesson survives the qualification. If the objective is meaningful wealth rather than maximum near-term income, percentage ownership and time in the asset matter more than the headline valuation.
Career security comes from a portfolio of hard experiences
Sam also pushed back on treating every career decision as a one-year compensation optimization.
If you only want to make money now, diligence the team. Do not anchor on one superstar rep. Look for several sellers hitting quota, meet them, and verify that the company already has product-market fit. A strong market can make a capable rep very well paid.
If the horizon is 10 or 15 years, the answer changes. Spend time at a company with real training. Spend time where the product is difficult and every meeting has to be earned. Learn what selling feels like when marketing is not handing you demand all day.
Early success can hide a weak foundation. A longer career benefits from knowing whether the result came from skill, market timing, or a product that was already pulling itself through the funnel.
AI raises the value of being unmistakably human
Sam is optimistic about AI, including its effect on sales. His point was not that no job will change. It was that companies still want to grow, complex buyers still want to speak with people, and new tools can make good operators more productive.
Nobody is casually buying a complicated $100,000 solution without human involvement. The systems may improve. Research, preparation, and follow-up may become faster. But trust, judgment, and the ability to understand another person's incentives remain part of the transaction.
That connects back to Pavilion. Sam wants to build an enduring institution that produces predictable cash flow and helps operators navigate a world that may become much more disorienting over the next decade. The more automated work becomes, the more useful a trusted group of actual people may be.
Give the full episode a listen. Sam connects compensation, ownership, career design, and AI with the kind of operator-level math that is easy to ignore until a high income has already narrowed your choices.
- Sam Silverman
Silverman Capital
