The Role

Pilot is building a first-of-its-kind, software-centric solution to tackle the financial back office (bookkeeping, tax, CFO, etc.) so that founders and business owners don't have to. Backed by Sequoia, Index Ventures, Stripe, and others, Pilot is rapidly growing its customer base in multiple SMB verticals.

As Head of Revenue Operations, you will be responsible for aligning and optimizing our S&M functions by influencing people, process, and data to maximize revenue generation and other revenue-related goals. You will play a crucial role in developing and implementing strategies that streamline our revenue-generating processes and enhance cross-functional collaboration. Reporting to the Director of Sales, you will be a highly visible contributor with the opportunity to build the RevOps organization at a scaling company.

Pilot is aiming to disrupt a $60B industry. Big, strategic, questions are being worked on by a diverse team of experienced but scrappy professionals. Collaborators wanted.

Key responsibilities

Create a clean, centralized, and standardized view of the end-to-end revenue funnel and associated KPIs enabling Pilot to (1) set the right targets, (2) surface risks & opportunities around execution, and (3) identify efficiencies.
Own the weekly sales forecast of the GTM business as well as partner closely with Finance on the GTM planning processes (ex: fiscal half, fiscal year, and long range).
Analyze data and generate insights to answer the next most important question for key stakeholders.
Own the calculation and execution of commission payments.
Develop and implement a strategy for the tools, processes, and people that make up GTM infrastructure.
Manage and develop current RevOps individual contributors.

About You

Proven ability to lead and scale Sales/Revenue Operations of significant scope through growth periods.
8+ years of experience in a fast-paced environment (consulting, business operations, RevOps or SalesOps or combination of).
2+ years of people management experience.
Excellent at Salesforce reporting and field and automation creation.
Can-do attitude; if you don’t know how to do something, you’ll learn it.
Strong analytical skills with the ability to translate ambiguous problems into actionable insights using data.
Strong capabilities in data analysis and modeling expertise.
Previous experience scaling SaaS companies strongly preferred.

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 and One Medical
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 $211,000 - $286,000 in San Francisco, CA. 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.