Salary
💰 $100,000 - $170,000 per year
About the role
- Pilot launched COO Services, a first-of-its-kind offering designed to provide hands-on operational support for early-stage startups and SMBs. This role will join our founding COO Services team and will be instrumental in delivering high-impact operational work while also helping shape the infrastructure, workflows, and automation that will define the product.\n
- As Principal COO Services, you’ll be responsible for directly working with customers, executing critical operational tasks (e.g., payroll, AP/AR, compliance, equity admin), and building scalable processes to make this a repeatable, high-value service offering.\n
- This position reports to Cole Levin (Head of Consulting Services) and will work closely with our internal teams to develop and refine COO Services into a scalable product. If successful, this role will evolve into a leadership position as the business line grows.\n
- Key Responsibilities:\n - Customer Operations Execution: Own day-to-day operational execution for early-stage startup and SMB customers, including payroll & benefits (Gusto, Rippling, Deel); Accounts Payable/Receivable; Equity Administration; Compliance & Tax Coordination; Bookkeeping & Financial Operations\n - Process & Product Development: Develop repeatable workflows, playbooks, and automation; identify AI opportunities; create internal docs; gather customer feedback; support scalability\n
- Who You Are: scrappy, execution-focused operator with a builder’s mindset; 6-8+ years in operational role; hands-on experience; customer-facing; strong process-building; tech-savvy; entrepreneurial; comfortable with ambiguity.\n
- Nice-to-Have: prior experience building internal infrastructure; familiarity with AI-driven tools; people management; expertise in HR/payroll/state compliance, expense management, audit-ready ops, quote-to-cash, cap table\n
- Why This Role: Pioneering opportunity; blend of execution & strategy; path to leadership; work directly with founders\n
- About Pilot: Pilot provides dedicated finance experts for small businesses; partners with Pilot Tax; extensive investors; etc.\n
Requirements
- 6-8+ years of experience in an operational role at a startup, SMB, or fast-growing business.\n
- Hands-on experience with payroll, AP/AR, equity administration, compliance, and financial operations.\n
- Customer-facing experience with the ability to interact with startup founders and SMB owners and serve as a trusted operational partner.\n
- Strong process-building and workflow automation skills – ability to turn ad hoc work into scalable, repeatable services.\n
- Tech-savvy with familiarity in tools like Gusto, Rippling, Carta, QuickBooks, Stripe, Zapier, Bill.com, Mercury, and Ramp.\n
- Highly entrepreneurial and an individual who thrives in ambiguity, takes ownership, and can execute with minimal direction.