Summary

At Pilot, we ingest over 7,000,000 transactions per year across more than 700 platforms — powered by a combination of expert human bookkeepers and AI agents working together. To support our fast-growing customer base, it's more important than ever to ensure that both our people and our automated systems can reliably access the data needed to produce accurate, high-quality financial reports.

We are hiring a Program Manager to support the Customer Operations teams. At Pilot, Customer Operations is responsible for delivering a high-value customer experience, producing high-quality month-end close accounting deliverables, and continuously improving processes through emerging technologies — including agentic AI.

This Program Manager is the key owner of all platform and financial data access processes at Pilot, for both human and AI-driven workflows. This person is process-oriented and thrives in problem-solving environments. You will work cross-functionally with our operations departments and with external platform partners to unblock access problems, document customer onboarding processes, and provide clear guidance to our operations team and AI systems on how to onboard customers and connect institutions to Pilot.

Key Responsibilities

• Manage admin console accounts and platform credentials, ensuring seamless access for both human operators and AI agents
• Work with external platforms to resolve access and integration issues across manual and automated workflows
• Produce and maintain accurate onboarding instructions for our customers
• Create and update internal documentation covering access provisioning, sync processes, and risk mitigation
• Maintain access- and platform-related ticketing queues, identifying patterns that could be resolved through automation
• Develop workflows and guardrails for accessing new institutions in compliance with Pilot guidelines
• Support and expand automation for platform onboarding, partnering with engineering and AI teams to reduce manual steps over time

About You

• Bachelor's degree or equivalent experience and 5+ years of relevant work experience in accounting/finance platform management, customer success, customer onboarding, or program management
• Systems thinker who can independently carry out rigorous, actionable analysis — and translate findings into processes that work for humans and machines alike
• Research-focused, with the ability to dive deep into complex platform access and integration problems
• Exceptional communication skills, with the ability to create clear, easy-to-follow processes for customers, internal users, and technical teams building AI tooling
• Genuine curiosity about AI and automation, with a willingness to actively experiment with agentic workflows — not just observe them
• Comfortable navigating ambiguity in a fast-paced, rapidly evolving environment where the line between human and AI work is shifting

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 3,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock.  Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene.  Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including wellness benefits such as Modern Health, Headspace, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

The base pay range target for the role seniority described in this job description is $62,000- $84,000 in Nashville, TN. Final offer amounts depend on multiple factors such as candidate experience and expertise, geographic location, total compensation, and market data. In addition to cash pay, full-time regular positions are eligible for equity, 401(k), health benefits, and other benefits; some of these benefits may be available for part-time or temporary positions.

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, information about requesting a reasonable accommodation in the job application process, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.