Principal, CFO Services

The Role

Every day, we do exciting work that makes a difference to startup founders and business owners. At Pilot, you will be helping clients solve critical financial and business strategy challenges. Our team works with a multitude of high-growth startup founders from different industries and stages as their trusted advisor and hands-on strategic finance consultant.

As a Principal on the CFO Services team, you will work with colleagues from leading tech companies, private equity, consulting, and investment banking firms. Together, our team delivers world-class strategic finance advice, fundraising consulting, and business transformation solutions. You will have endless opportunities to be a problem solver, creative thinker, and new business builder.

That’s life at Pilot. It could be for you.

Key Responsibilities

This is a senior role responsible for both executions and outcomes in working directly with our clients to:

• Develop and possess a subset of CFO Services opportunities across various industries and products.
• Implement rigorous problem-solving to help solve clients’ most complex issues on how to grow their businesses and manage their resources
• Own proactive communication with clients regularly to provide our recommendations, anticipate their challenges, and exceed expectations.
• Bring the latest analytical techniques plus a deep understanding of industry knowledge to help clients develop financial models, budgets, and forecasts.
• Research the latest developments and formulate insights into the clients’ industry to be a strategic partner for the clients in a scalable manner.
• Be part of the world’s leading tech-enabled firm’s financial services, acting as a trusted advisor for our clients on critical financial and business decisions.
• Build long-term relationships and drive superior financial returns based on unique business insights across multiple customers.
• Support the development and execution of innovative go-to-market strategies by building your network within the startup ecosystem, collaborating with sales & marketing, and identifying new product opportunities for our clients.
• Partner with clients to help them deliver measurable and sustainable improvements in financial and business KPIs.
• Lead the preparation of key deliverables for investor discussions and board meetings, including KPI analysis, financial models, and strategic recommendations.
• Oversee the ongoing management of budgets, variance reports, and rolling forecasts to ensure business plans are on track.

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

• Identify areas of opportunity inside and outside of Pilot CFO Services and develop strategies to capitalize on them.
• Lead structural improvements that influence CFO Services into the broader organization.
• Ensure commitments to major initiatives are fully executed, and all loose ends are tied.
• Mentor and coach junior team members, providing guidance and support to help them grow into future leadership roles.
• Develop and spearhead process improvements to maximize accuracy and efficiency within Pilot’s offering.

About You

We are looking for people who demonstrate these aspects:

• 10+ years of relevant finance and strategy experience, including previous experience in investment banking, consulting, or fast-growing company environments.

  • MBA or other advanced degree preferred but not required

• Experience leading go-to-market strategies or playing a key role in client acquisition, business development, or market expansion.

• Exposure to technology, manufacturing, healthcare, or business services sectors, or experience leading internal functions at startups or small/medium-sized business (preferred but not required).

• Advanced Excel modeling skills with the ability to own financial models end-to-end, as well as ensure their quality, timeliness, and accuracy.

• Ability to operate in ambiguity, break complex situations down into smaller work units, and delegate effectively.

• Highly analytical with the ability to consume, process, and prioritize large amounts of unstructured information.

• Exceptional verbal and written communication skills, with the ability to translate complex data into clear and actionable insights.

• Highly entrepreneurial, proactive, and able to thrive in ambiguity and fast-paced environments.

• Proven ability to build strong collaborative working relationships across teams, junior members, and cross-functional partners.

• 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 1,000 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 $146,000 - $247,000 in most remote locations, and between $182,000 - $247,000 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, recruitment agency policy, recruitment scam notice, and important E-Verify information. You may view our job candidate privacy policy here.