The Crew · Nov 4, 2026
Growing From Founder to 34 People Without Losing the Team You Built
Every winery that outgrows the founder-does-everything stage hits the same wall: the practices that kept five people loyal do not automatically scale to thirty. Here is how to decide which of your informal perks become written policy before your next hiring push.
Drea Helfer built DH Wine Compliance into what Wine Industry Advisor describes as the largest alcohol compliance consulting firm in the country, now at 34 employees. She talked through her family-forward management practices on the Small Fortune podcast with host Carol Collison. The number worth sitting with is 34, because that is roughly where most beverage businesses stop being a crew and start being a company.
You know the stage. At six or eight people, flexibility is a handshake. Someone needs to leave at 2 for a kid's game, you say yes, everybody understands. Nobody writes it down. At 25 or 30, the same handshake becomes a fairness problem, because now there are people who do not have your cell number and do not know what was promised to whom.
You have three options, and none of them are free.
- Keep it informal. Cheapest, fastest, and it works until two people compare notes and one of them feels cheated. Risk goes up with headcount.
- Write the practices down as policy. Costs you a few days and some handbook help, and it removes your discretion. The upside is that a new tasting room hire in month one gets the same deal as your ten-year cellar lead.
- Formalize selectively. Put scheduling flexibility, time-off approval, and shift-swap rules in writing. Leave bonuses and one-off help as case-by-case so you keep room to be generous.
I'd take the third. Write down what people compare against each other, keep flexibility on the rest.
One caution: when informal practices become written policy, you can create wage and hour obligations you did not intend, particularly around flexible hours, on-call time, and whether a role is exempt. Have employment counsel in your state review the language before you hand it out. Pay benchmarks for this kind of role were not in the source, so do not treat any of this as a compensation guide.
Block 90 minutes this week and list every informal promise you have made to a staff member in the last year. That list is your handbook draft.