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 Manager on the Consulting Services team, you will serve as the key finance partner to a portfolio of businesses, acting as both a trusted advisor and a hands-on operator.

You will support founders in navigating 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 support 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 day-to-day financial management for a portfolio of client engagements as a primary finance partner to founders and executive teams
• Build strong, trust-based client relationships through high-quality execution and sound judgment
• Build, maintain, and continuously improve three-statement financial models and rolling forecasts
• Lead monthly budget vs. actuals analyses and communicate clear insights and recommendations
• Support strategic initiatives such as fundraising preparation, pricing analysis, sales compensation modeling, and go-to-market planning
• Advise on cash runway management, unit economics, and operational performance tracking
• Prepare board materials and investor updates with clear, data-driven insights
• 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 internal process improvements and the continued evolution of Pilot’s Consulting Services delivery model
• Support progress against team OKRs through disciplined execution and cross-functional collaboration 

About You

You have strong financial fundamentals and are comfortable working directly with founders and senior leaders.

Required Experience:

• 3–6 years of experience in management consulting, investment banking, private equity, venture capital, or strategic finance at a high-growth company
• Strong financial modeling skills (Excel/Google Sheets), with the ability to build and maintain three-statement models independently
• Experience supporting executive decision-making through structured analysis
• Clear and concise verbal and written communication skills
• Proven ability to manage multiple priorities and deliver high-quality work with attention to detail

You are:

• Analytical and detail-oriented
• Comfortable balancing structured analysis with practical business judgment
• Proactive and able to operate with autonomy
• Energized by working directly with founders and leadership teams
• Adaptable in fast-moving, ambiguous environments

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 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 $116,000 - $149,000 in most remote locations, and between $145,000 - $165,000 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.