Executive Assistant to the Co-Founder

Title: Executive Assistant to the Co-Founder, Cherry Net Inc Greenpoint, Brooklyn, in-person 4 days/week $55-80K base + ESOP Cherry Net is a VC backed, fast growing B2B payments company serving the long-term care industry. The founder side is operationally stretched, and this role exists to fix that. Specifically: to take over the calendar, inbox, books, follow-ups, hiring coordination, and recurring admin so the founder can stay in the work only he can do. This is not a typical EA role. This is an EA role for someone who naturally takes ownership of outcomes. Calmer than the founder, more methodical, more comfortable with structure. Complementary, not similar. You exercise judgment about which problems deserve your intervention, which should stay lightweight, which are noise, and which belong to someone else. You triage with judgment and act with precision. You'll know you're the right fit if you read this and think: "I notice patterns, I pick up dropped balls before anyone sees them, I show up with draft solutions instead of problem reports, and I don't need to be told twice." What you'll do Run the founder's calendar and inbox. Shared inbox to start, drafting in his voice. Earn into his full inbox over time. Keep our internal corporate books clean and audit-ready in QuickBooks. Light weekly load, first-of-month billing takes a few hours. Absorb the recurring operational work that pulls the founder out of revenue: insurance issues, customer escalations, refund coordination, audit scheduling, and vendor follow-ups. Coordinate hiring end-to-end: job posts, resume screening, scheduling, reference checks, onboarding logistics. Build it into a reusable system as we go. Track commitments and own the follow-up loop on things the founder is responsible for. Document recurring workflows as you take them over, so the operational layer scales beyond your head. What I'm honest about up front I'm not a structured teacher. You'll get hands-on training in week one, but written playbooks aren't coming. This role works best for people who enjoy learning by extracting context in real time, asking sharp questions, taking notes, and bringing drafts back for me to verify. You'll get autonomy fast. Trust earns trust. Once pattern recognition is proven, I get out of your way. The role is operational first. Real exposure to how a B2B payments company runs comes with the seat, but the deliverable is execution, not strategy. What you bring 3-5 years administrative experience, ideally supporting a founder or operator at a small, fast-moving company. Fortune 500 or big-agency EA backgrounds are usually not the fit. Working QuickBooks fluency. Standard SMB books. You can run day-to-day cleanly and prep for an audit. Hands-on experience managing someone else's calendar and inbox, including drafting on their behalf. Clean precise writing. Your drafts go to customers, vendors, partners, and occasionally counsel. Steady under pressure. The role absorbs curveballs and you handle them without panicking or dropping the rest of your plate. Judgment and a backbone. Sometimes you'll be the first contact on requests that smell wrong. We need someone who slows down when something is unclear and doesn't bend to charm or urgency. AI as infrastructure, not novelty. You already use ChatGPT, Claude, or similar tools daily and reach for them as a first instinct. Trustworthy with confidential financial, HR, and security information. Background check and references mandatory. What we offer $60-80K base, depending on experience. ESOP participation. Real upside in the equity for people who join now. In-person 4 days/week in our Greenpoint, Brooklyn office, working directly alongside the founder. And Medical. How we hire Send your resume and a short note (under 200 words) telling us about a time you noticed a problem your boss didn't see yet, and what you did about it. Skip the cover letter. Skip the formality. The note is the screen. If you make it past the note, we do a 20-minute phone screen. The final stage is a working session built around real Cherry-style problems. References, offer. Pay: $55,202.90 - $80,000.00 per year Benefits Health insurance Paid time off Work Location: In person