General Partner
David Cautin is a two-time CEO, a board director to private-equity-backed companies, and a General Partner at Enjoy The Work, where he advises venture-backed founder-CEOs on the decisions that punish inexperience: raising capital, finding customers who stay, and hiring the people who will run the company. Thirty years of operating history sit behind the advice.
I’ve made these decisions before.
Most founders are making them for the first time.
Raise it, or sell it. Term sheets, diligence, investor dynamics, and the negotiation itself. The round you can raise is a function of the company you have built and the investors who actually exist.
Make the curve bend. Segmentation, positioning, lead generation, sales, and what happens after the sale. When growth stalls the cause is rarely effort; it is usually that the motion you have and the motion the market rewards are two different things.
Run it so the rest is winnable. Cadence, goals, board management, and hiring, with one coherent set of numbers from the financial model down to the individual contributor.
A few of the founder-CEOs he works with on capital markets, go-to-market, and scaling.
The first session is about the founder, not the company. How they learn, what gives them energy and what drains it, what they believe about their market that other smart people do not, and the one thing they are most afraid to tell him. Then the company in the same detail: how it makes money, where the go-to-market has already pivoted, cap table, board, burn, and the leadership gaps to fill inside a year. The session closes by imagining the year is over and it went extremely well, then asking why it did not. The gaps between the company they have and the company that goal requires are the work.
Boards don't lose faith because of bad news. They lose faith when the CEO can't explain what changed.
David Cautin, General Partner at Enjoy The Work
Alongside the advisory work, David sits on the boards of private-equity-backed companies, usually mid-market businesses between $100M and $500M in revenue, and usually in situations where the plan and the results have diverged.
4
exits
$1B+
raised in debt and equity
36+
companies bought or sold
Over thirty years David has served on the management team of two Fortune 500 companies and the leadership team of two venture-backed companies, co-founded his own startup, and been CEO of two private-equity-backed businesses, across B2B SaaS, healthcare, financial services, services, and consumer, in the United States and Europe. What matters more than the totals is the range: buying and selling are not the same skill, and they are usually learned separately. He has raised money and he has been the person deciding whether to give it, which is why he can tell a founder what the other side of the table is actually optimizing for.
David has been a partner at Enjoy The Work for more than five years. The base methodology is the firm's, built and refined across hundreds of companies, and he teaches it freely. What he adds is the operating history behind it.
