Operating advisory for owner-led companies

I’ve made the mistakes.
You don’t have to.

I cofounded Billd, a fintech company, and helped grow it from zero to eight figures in a few years. I got a lot wrong and right along the way, and I bring those lessons to owners of growing companies, so you hire better, move faster and make fewer mistakes.

Sound familiar?

What owners tell me in the first meeting

What you sayWhat's usually going on
"I've made three bad hires in a row."No scorecard, unstructured interviews, and a role nobody defined. Usually the problem isn't the person. It's the seat.
"Everything runs through me."No second layer of leaders, and no clear owner for each part of the business.
"We're busy, but nothing moves."No short list of priorities, no weekly rhythm, and no one holding people to either.
"I don't know what next year looks like."No plan, or a plan that went in a drawer in February.

How it works

Start small. Keep what works.

  1. 01

    Hire Check or Truth Session

    A no-cost first look at one real problem: your last three hires, or your top three issues. You get a one-page memo on what each one costs and what to fix first.

  2. 02

    The Truth Audit

    I interview each of your leaders, profile how your team works, and hold your org chart up against your goals. You get a plain account of the gaps: the seats that are empty, the ones filled by the wrong person, and the ones nobody owns.

    Leader interviewsWork style profilesOrg chart reviewGap analysis
  3. 03

    Jester Rhythm

    An ongoing retainer. We meet for an hour every week. I run your hiring for one open role at a time, from the scorecard through the final debrief. Each quarter we spend a half day setting priorities, and you can reach me between meetings.

    Weekly owner meetingHiring supportQuarterly planningMonth to month
  4. 04

    The Year Plan

    A full day each fall to set the next year: a three-year picture, one-year goals, budget targets, and the org you'll need to hit them.

Planning 2027? From now through January, the Truth Session can be a 2027 planning session. Bring your numbers and your doubts.
Flat fees, never hourlyYou know the cost up front.
Month to monthNo long contracts.
Clear scopeWritten into the agreement.

Who it's for

Growing, owner-led, and feeling the strain

Usually

  • $3M to $50M in revenue, 10 to 150 people
  • Founder or second-generation owner, no COO yet
  • A leadership team of three to eight
  • Hiring five or more roles a year

Often right after

  • Crossing $5M or $10M
  • Losing a key person, or a bad hire
  • Hiring a first GM or COO
  • Getting ready to sell, or a family handoff

About

An operator, not a career consultant

Jesse Weissburg

At Billd, I've made the hires, run the leadership meetings, and lived with the mistakes. We ran EOS, then rebuilt it into a leaner system that fit a company our size.

Most people who advise owners have never been the one making the call. I have, and I still am. Jester is how I bring that to a small number of owners outside my own company. I keep it to a few clients at a time, so you work with me directly.

Jesse WeissburgFounder, Jester · Annapolis, Maryland
The jester was the only one in court who could tell the king the truth.

Owners are surrounded by people who report to them. I don't. My job is to tell you what your team won't, while it's still cheap to fix.

Next step

Tell me what's hard right now.

Thirty minutes, no pitch. If I'm not the right fit, I'll say so and point you to someone who is.