Chief of Staff & Business Operations Lead

The Role

Pilot is building a first-of-its-kind, hybrid software/service solution to tackle the financial back office (bookkeeping, tax, CFO, etc.) so that founders and business owners can focus on building and running their businesses. We already work with 1,700+ customers in the tech startup and SMB sectors, and we are expanding rapidly.    The Customer Operations department is 125+ employees that partner with our customers to manage their accounting back office and support them in their business goals. This is a leadership role that supports the VP Customer Operations as their Chief of Staff as well as managing a small team of Business Operations Managers.    The Chief of Staff will play a critical role in supporting the VP of Customer Operations in major decision-making processes and acting as a key conduit for the operations team. This role requires a strategic thinker with excellent organizational and communication skills, capable of handling confidential information with discretion. This is a high impact role that will have a front row seat into how the key decisions are made at Pilot.   This role will drive the priorities for the department, work on critical initiatives for the business, set shared goals with cross-functional organizational leaders, develop multi-year roadmaps with specific actions needed to achieve goals across the enterprise, ensure that resources are prioritized and committed to achieve strategic goals and desired outcomes, monitor whether actions achieved intended goals, and revise future strategy and plans accordingly.   Customer Operations is based in Nashville, TN. This role is available both remote and in office (flexible on-site schedule).   

Key Responsibilities

• Data-Driven Insights: Leverage analytics to evaluate business performance and make informed decisions. Prepare reports and presentations to support leadership in strategic planning and decision making.
• Resource Management: Oversee company resources, including budget, personnel, and tools, ensuring they are efficiently allocated to meet business needs.
• Project and Change Management: Lead key initiatives and projects to drive business growth, working with various teams to ensure milestones are met on time and within budget and helping drive that change with clear communications and/or training materials
• Process Optimization: Identify and implement improvements in business processes, workflows, and internal systems to maximize operational efficiency.
• Vendor Management: Manage relationships with third-party vendors, ensuring that services meet company standards and contracts are cost-effective.
• Strategic Leadership: Participate in strategic planning sessions and help translate high-level strategies into actionable plans.
• Culture Stewardship: Foster a positive, inclusive, and high-performance culture within the operations team and across departments. Act as a role model, championing company values and promoting collaboration, transparency, and continuous improvement.

About You

Need to haves:

• Leadership Experience: 7-10+ years of experience in business operations, strategy, or senior project management roles, with at least 5 years in a leadership capacity, ideally in a start-up or technology-forward environment.
• Strategic & Financial Acumen: Strong business acumen with experience in financial analysis, forecasting, and strategic planning with demonstrated experience on how to translate operational drivers into both business demand and financial impacts of the business.
• Technical Proficiency: Proficiency in business operations software, data analytics tools (e.g., GSheets, SQL, Looker), and business modeling (both financial and operational).
• Project Management: Demonstrated experience in leading large, cross-functional projects to achieve successful business-level outcomes and accompanying change adoption.
• People Management: Experience managing a team and mentoring/upleveling reports and colleagues.
• Exceptional Communication Skills: Excellent verbal and written communication skills, with the ability to influence and collaborate with senior stakeholders across the organization, serving as the “glue” across teams.

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, Headspace, 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 $87,000 - $170,000 in most remote locations, and between $126,000 - $216,000 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.

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