About Hum Capital

Hum Capital is an intelligent capital markets and structured lending platform. We have invested in 65+ companies through our direct lending franchise, deploying capital across software, services, healthcare, and asset-heavy operating businesses. Over the past decade we have built more than $65M of proprietary technology — origination, underwriting, servicing, and now agentic AI tooling — that gives us an information and execution advantage no other lender in our segment has.

Our mission is to make growth capital equitable, efficient, and accessible — and to create real alpha for our LPs by being the most useful capital provider our borrowers have ever worked with.

The Role

This is not a traditional Chief of Staff seat. You will not be running Blair's calendar.

You will be the person Hum sends in when a portfolio company breaks. You will drop into a borrower in Portland, or Tampa, or Phoenix, sit down next to the CEO, and fix the thing that is broken — usually within days or weeks, not months or quarters. Then you will move to the next one.

The thesis is straightforward: Hum has invested in 65 great teams running mostly profitable, mostly unsexy businesses. Many are not yet AI-native. There is real, measurable alpha to be unlocked by dropping a high-agency operator with modern tooling directly into the seat next to the CEO. Firms like Shore Capital have proven the playbook in healthcare services (we recommend the Justin Ishbia interview on Invest Like the Best — it should genuinely excite you). AI tooling has compressed the timeline and widened the spread. Our portfolio is the proving ground.

You will work hand-in-hand with Blair Silverberg, Hum's founder and chairman. This is a mentor / mentee relationship by design. If you do this job well, the next step is yours to choose: run one of these companies, found your own, or lead an investment strategy inside Hum.

What You'll Actually Do

• Drop into a portfolio company — typically 2 to 8 weeks at a time — and work directly with the CEO to diagnose and fix a specific, named problem. Examples we have run recently: a stalled collections function, a broken sales motion, a CFO transition, a botched ERP migration, a pricing system that is leaving 8 points of margin on the table.
• Build, in days, what the company's team thought would take a quarter. We expect you to be on the frontier of applying modern AI tooling — Claude, Claude Code, agentic systems, modern data stacks — to compress the timeline of every operating problem you touch.
• Ship measurable impact. Every engagement ends with a number: cash collected, margin recovered, cycle time cut, headcount avoided, revenue unlocked. If you cannot point to the number at the end, the engagement did not happen.
• Light a fire under the existing team. The teams at these companies are competent — that is why we invested. Your job is not to replace them. It is to show them what is possible with a modern operating posture, hand them the playbook, and move on.
• Sit next to Blair on the deals where the situation is most urgent or the lever is most concentrated. Co-author the workout strategy. Co-author the board memo. Carry the meeting when Blair is in the next one.
• Build the value-creation playbook. The first three or four engagements are the foundation; by engagement eight you should be writing the SOP that the next person on this team runs.
• Finally, sometimes it's better to sell than to fix a company. In these situations, you'll be responsible for identifying and securing the appropriate banker, overseeing their process, and ultimately ensuring sale and liquidity at the best price the market can offer within our timeframe.

Who You Are

• Energetic and have enough operating or investing reps that you are not learning the basics on our dime, but early enough in your career that you still think in days, not quarters.
• Demonstrably on the frontier of applying AI to real business problems. We will ask you, in detail, what you have built. "I use ChatGPT a lot" is not an answer. "I shipped an agentic workflow that replaced three FTEs of work at my last company" is.