Senior Manager, Strategic Finance

The Role 

At Pilot, we partner with founders and executive teams to help them make high-impact financial and strategic decisions. As a Senior Manager on the Consulting Services team, you will serve as the strategic finance lead to a portfolio of businesses, acting as both a trusted advisor and a hands-on operator.

You will guide founders through growth tradeoffs, margin expansion, hiring plans, pricing strategy, fundraising readiness, and long-term financial planning. You’ll bring structure to ambiguity and translate financial performance into clear, actionable insights.

While each engagement is grounded in strong FP&A fundamentals, including building and maintaining robust three-statement models, your impact will come from how you interpret the data, challenge assumptions, and guide executive decision-making.

You won’t be siloed into a single vertical. Instead, you’ll work across industries and stages to help founders build durable, scalable businesses.

Key Responsibilities

• Own a portfolio of client engagements as the primary strategic finance partner to founders and executive teams
• Build long-term, trust-based client relationships grounded in sound judgment and measurable impact
• Lead companies through critical inflection points such as fundraising, M&A evaluation, pricing and packaging strategy, sales compensation design, and go-to-market decisions
• Advise on capital allocation and investment prioritization, cash runway management, unit economics, and long-term financial planning
• Shape board narratives and support investor communications with clear, data-driven insights
• Build and maintain financial models and forecasts, using them as decision-making tools — not simply reporting outputs
• Leverage AI and automation to improve financial workflows, analytical efficiency, and forecasting accuracy

In partnership with the team and cross-functional partners, you will also:

• Contribute to the continued evolution of Pilot’s Consulting Services offering and delivery model
• Own and drive progress against Consulting Services team OKRs, translating strategic priorities into measurable results 
• Mentor and guide junior team members as they develop their strategic finance and client leadership capabilities

About You

You’ve operated at a strategic level and are comfortable influencing executive decisions.

Required Experience:

• 7+ years of experience in management consulting, investment banking, venture capital, strategic finance, or senior finance leadership roles
• Experience advising founders or executive teams on high-impact financial and strategic decisions
• Strong financial modeling fluency (Excel/Google Sheets), with the ability to use models as strategic decision-making tools
• Exceptional verbal and written communication skills, with executive presence
• Proven ability to synthesize complex information into clear, structured recommendations
• Experience leading complex financial engagements and managing junior team members to deliver high-quality outcomes
• Demonstrated ability to build strong collaborative working relationships across teams and functions

You are:

• Comfortable operating with autonomy and ownership
• Skilled at balancing analytical rigor with sound business judgment
• Energized by working directly with founders and leadership teams
• Entrepreneurial and comfortable in fast-moving, ambiguous environments
• Detail-oriented, with high standards for accuracy and quality

Note: This position is only available for remote employment in the United States in the following states: CA, GA, NY, NC, TN, TX, and WA.

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, Headscape, 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 $136,000 - $170,000 in most remote locations, and between $170,000 - $190,000 in San Francisco, CA and New York City, NY. 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.