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CHIEF OF Staff

Pear VC

Job TitleThis is not an EA role, and not a strategy role — it's a hands-on generalist operator who owns the business, legal, and people infrastructure that lets a small team move fast without breaking.You'll be the person who makes sure the company runs: contracts get signed, people get paid, compliance holds up, and nothing critical falls through the cracks. You'll work directly with the founders and build the operational backbone from close to zero.Legal, HR, accounting, payroll, compliance, and day-to-day operations all sit on the founders' plates today, alongside product and engineering. In a healthcare company, this surface area is heavier than usual — BAAs, HIPAA and state privacy obligations, and customer contracts can't be an afterthought. We need one person to own all of it end to end: not just execute tasks, but build the systems, vendor relationships, and processes so these functions run reliably as we scale.Legal & contracts — manage outside counsel, own the contract lifecycle (customer agreements, BAAs, NDAs, vendor and consulting agreements), and keep corporate housekeeping in order: cap table administration, board and investor documents, entity and state registrationsCompliance — own the operational side of HIPAA and state privacy compliance, coordinate audits and security certifications (e.g. SOC 2) as they come up, and maintain the policies, records, and vendor due-diligence that customers and regulators expectHR & people ops — run onboarding/offboarding, offer letters, benefits and PEO administration, immigration/visa support for the team, and keep employee policies and records clean and currentAccounting & payroll — own bookkeeping oversight with our accountants, run payroll and contractor payments, manage AP/AR, expenses, banking, and the monthly closeEveryday operations — manage vendors, software and tooling, insurance, and the logistics of a fast-growing team; be the default owner for the operational thing no one else is holdingFounder leverage — take ambiguous operational problems off the founders' plates, structure them, and drive them to doneA generalist who's comfortable owning many unrelated functions at once and context-switching cleanly between themStrong execution and follow-through — you close loops and things don't slipHighly organized and detail-oriented, with good judgment about what's genuinely important vs. merely urgentOperates in ambiguity and builds process where none exists, without waiting for perfect instructionsTrustworthy with sensitive legal, financial, and personnel informationWilling to do unglamorous, high-value workFast learner with genuine interest in the operational and regulatory side of a healthcare companyPrior chief-of-staff, business ops, or startup operations experienceExposure to legal, HR, finance, or compliance functionsFamiliarity with healthcare compliance (HIPAA, BAAs) or other regulated environmentsExperience standing up processes and vendors at an early-stage companyDirect, daily work with the founders, plus exposure to board and investor conversationsTrue zero-to-one scope — building the operational foundation of the company, not executing a fixed playbookCompetitive salary and meaningful equity

Vacancy posted 1 day ago
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