What we're building

Every company needs to keep track of its finances, and most hire a bookkeeping firm to help do so. But there's no Stripe, Gusto, or Google Apps of this world—no clear best-in-class firm that everyone uses because it delivers a service of unmatched quality and integrates with the tools and workflows to run your business as it grows. Pilot is building a first-of-its-kind, software-centric solution to tackle the financial back office (including bookkeeping, tax, CFO, etc.) so that founders and business owners don't have to.
Our approach is to use software to automate as much of the heavy lifting as possible and to give those software superpowers to a team of finance experts. This means that our customersbusiness ownerscan focus on the reasons they started their businesses in the first place, instead of worrying about whether their bookkeeping is being done well.

The role

Pilot’s product is a set of financial services delivered by in-house finance experts. We build sophisticated software that these experts leverage to automate and simplify financial processes and aid in their analyses. The result is a radically improved financial experience, with unparalleled quality, customer support, and financial insights no other provider has.
Pilot is looking for a Head of Product to lead our Product and Design teams as Pilot enters its next phase of growth: bringing not just bookkeeping, but the full financial back office, into the 21st century.
You will partner closely with our founders, Engineering team and Operations leads to drive our product strategy and product development process.
The responsibilities of this role include:
  • Own and deliver on company-level business objectives.
  • Build and inspire a high performing, diverse team of Product Managers and Designers. Help develop their careers and assign them to projects tailored to their skill levels, personalities, work styles, and professional goals.
  • Work closely with stakeholders from across the business to develop and inform a cohesive product strategy while strengthening relationships between Product, Engineering, Design, and Operations.
  • In partnership with the Head of Engineering, run an effective quarterly planning process that is inclusive of our internal customers.
  • Define strong and consistent processes for continuously gathering input from both internal and external users.
  • Cultivate Pilot as a center of Product and Design craft excellence.
  • Create an environment that fosters high quality, metrics-driven product development and leads to impactful improvements to our automation and service offering.

About you

Our Head of Product will need to balance their time between being hands-on at the project level and working with our executive team on strategy. As our ideal candidate, you’ll have a strong track record of delivering business results as a hands-on product manager, as well as a strong track record of stewarding a high-performing team as a people manager.
Additionally, you’ll be able to demonstrate experience with the following:
  • Working with executive stakeholders and cross-functional partners to set and communicate product strategy.
  • Translating ambiguous or complex ideas into clear, executable projects and delivering outcomes.
  • Leading the cross-functional planning process for a department or team.
  • Hiring, including demonstrated success with attracting senior Product and Design talent. You can identify the need for headcount, define hiring criteria, and act as an owner throughout the entire recruiting lifecycle.
  • Managing direct reports’ performance. This could include managing out, performance corrections, giving continuous feedback, identifying goals and stretch assignments, and investing in strong performers.

About us

Our 35-person Product, Engineering, and Design org is split into three teams, each with their own missions and charters.
In total, Pilot is 140+ people split across our San Francisco and Nashville offices. Our Product, Engineering, and Design teams are in our San Francisco office, right next to the Montgomery Street BART stop — though right now we are all working from home. We are currently only considering candidates who live in or will relocate to the San Francisco Bay Area post-COVID.
Our seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox), and our managers have a breadth of experience at companies of varying sizes. We invest in managers via peer mentorship and forums that meet at least quarterly across all functions.
We offer competitive benefits, including medical, dental, and vision coverage, as well as a 401(k) program.
At Pilot, we are enthusiastically pursuing and hiring a diverse workforce. We do not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender-identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws. However, we do encourage applicants of all backgrounds and identities to apply.
Pilot also welcomes the opportunity to consider qualified applicants with prior arrest or conviction records. Pilot’s demonstrated commitment to diversity extends to hiring talented individuals in spite of a prior criminal history in accordance with local, state, and/or federal laws, including San Francisco’s Fair Chance Ordinance.

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