Principal COO Services

The Role

Pilot is launching COO Services, a first-of-its-kind offering designed to provide hands-on operational support for early-stage startups and SMBs. This role is our first hire for COO Services and will be instrumental in delivering high-impact operational work while also helping shape the infrastructure, workflows, and automation that will define the product.

As Senior Manager, 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.

This position reports to Hudson Bova (Head of CFO 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.

Key Responsibilities

This is a high-impact, high-autonomy role that combines hands-on execution, process-building, and productization:

Customer Operations Execution

Own day-to-day operational execution for early-stage startup and SMB customers, including:

• Payroll & Benefits: Setup and management using providers like Gusto, Rippling, Deel.
• Accounts Payable/Receivable: Defining and executing efficient AP/AR workflows.
• Equity Administration: Managing cap tables, equity grants, and vesting schedules via Carta or Pulley.
• Compliance & Tax Coordination: Working with Pilot Tax and partners like Mosey to ensure regulatory compliance.
• Bookkeeping & Financial Operations Support: Integrating with Pilot’s core bookkeeping product.

Process & Product Development

• Develop repeatable workflows, playbooks, and automation to streamline service delivery.
• Identify opportunities for AI and automation to reduce manual work and improve efficiency.
• Create internal documentation and build scalable service infrastructure.
• Gather feedback from customers to help shape the future roadmap of COO Services.
• Support long-term scalability by identifying operational bottlenecks and implementing solutions.

Who You Are

We are looking for a scrappy, execution-focused operator with a builder’s mindset. The ideal candidate has hands-on operational experience in early-stage startups or SMBs and is excited by the challenge of both doing the work and building the playbook for scaling it.

Must-Have Qualifications

• 6-8+ years of experience in an operational role at a startup, SMB, or fast-growing business.
• Hands-on experience with payroll, AP/AR, equity administration, compliance, and financial operations.
• Customer-facing experience with the ability to interact with startup founders and SMB owners and serve as a trusted operational partner.
• Strong process-building and workflow automation skills – ability to turn ad hoc work into scalable, repeatable services.
• Tech-savvy with familiarity in tools like Gusto, Rippling, Carta, QuickBooks, Stripe, Zapier, Notion, Airtable.
• Highly entrepreneurial and an individual who thrives in ambiguity, takes ownership, and can execute with minimal direction.

Nice-to-Have Qualifications

• Prior experience building internal infrastructure for an early-stage business.
• Familiarity with AI-driven operational tools and automation.
• Previous people management experience (or interest in growing into a leadership role as the team scales).

Why This Role?

• Pioneering Opportunity: You’re the first hire for a new service line, with a direct impact on shaping how it operates and scales.
• Blend of Execution & Strategy: You get to do the work, while also building the playbook and productizing the service.
• Path to Leadership: If COO Services scales, you’ll have the opportunity to grow into a leadership role.
• Work Directly with Founders: Gain firsthand experience working with early-stage startup leaders, solving their operational challenges.