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 –