Pilot is building a first-of-its-kind, hybrid software/service solution to tackle the financial back office (bookkeeping, tax, CFO, etc.) so founders and business owners can focus on building and running their businesses. We work with thousands of customers in the tech startup and SMB sectors, and we're growing quickly.
Customer Operations is made up of 150+ employees who partner with our customers to manage their financial back office and support their business goals. This is an individual contributor role reporting into the Head of Business Operations, working closely with Customer Operations service delivery teams, cross-functional partners, and peer Business Operations Managers.This role sits at the center of how we plan, allocate, and forecast work across the organization, and increasingly, how we automate that work. Pilot is moving fast toward agentic, AI-assisted operations, and this person will build and own the systems, models, and reporting that make that shift possible: work orchestration, KPI reporting, resource forecasting, and billing. This isn't a role for someone who wants to build one dashboard and maintain it. It's for someone who wants to keep building better systems as the work itself changes.
The role requires real fluency with data and automation tools (Excel/Sheets at an expert level, plus a builder's instinct for where AI and scripts can replace manual work), sharp attention to detail, and good judgment about what results imply for our strategy and performance. This person works directly with senior leadership.This is a hybrid in-office role based in either our San Francisco or Nashville office.
- Work Orchestration: Own the systems and processes that plan and allocate work across the organization. Build and maintain the models that route work efficiently as volume, team capacity, and service lines change.
- KPI Reporting: Build and maintain reporting that gives leadership a clear, accurate, real-time view of business performance. Know the data well enough to catch anomalies before they become someone else's problem.
- Resource Forecasting: Build and maintain forecasting models that project staffing and capacity needs against demand. Translate forecasts into recommendations leadership can act on.
- Billing Operations: Own billing sheet accuracy and process, including the reconciliation and QA that keeps them error-free at scale.
- Automation & AI Adoption: Identify where manual, spreadsheet-based, or repetitive work can be automated or AI-assisted. Build these solutions directly rather than just recommending them, using tools like Excel/Sheets scripting, SQL, and emerging AI tooling.
- Process Optimization: Identify and implement improvements to the processes, workflows, and systems this role owns, so accuracy and efficiency improve as the business changes. When an improvement requires cross-functional buildout, lead it end to end, including the change management to get it adopted.
- Experience: 3-5 years in business operations, analytics, or finance, ideally in a start-up or technology-forward environment, with a track record of actually building and running a system. Experience owning forecasting, billing, or resource-planning is a strong plus.
- Technical Proficiency: Expert-level Excel/Sheets (formulas, modeling, automation/scripting), plus working proficiency in SQL and analytics tools (e.g., Looker). Comfort using AI tools like Claude Cowork.
- Detail Orientation: A track record of getting the numbers right the first time.
- Systems Thinking: Able to see how planning, allocation, forecasting, and billing connect, and to design solutions that account for the whole picture rather than one piece of it.
- Project Leadership: Demonstrated experience leading the build or overhaul of an operational system, including the change management needed to get a team to adopt it.
- Communication: Strong verbal and written communication skills, with the ability to work directly with senior leadership and translate technical or data-heavy work into clear recommendations.
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 additional wellness benefits
- 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 $72,000 - $105,000 in Nashville, and between $97,000 - $136,000 in San Francisco, CA. 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.
Skills Required
- 3-5 years in business operations, analytics, or finance
- Experience building and running operational systems and leading system implementation/change management
- Experience owning forecasting, billing, or resource-planning
- Expert-level Excel and Google Sheets including formulas, modeling, and scripting/automation
- Working proficiency in SQL
- Experience with analytics tools (e.g., Looker)
- Comfort using AI tools (e.g., Claude Cowork) and identifying automation opportunities
- Strong attention to detail and track record of accuracy
- Strong verbal and written communication skills; ability to work with senior leadership
What We Do
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.
Why Work With Us
Pilot is truly a diverse company. We embrace people from all backgrounds including those who were formerly incarcerated. In addition, with our high growth environment we love to promote people within and offer them great career opportunities.
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