Head of Data

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 giving those software superpowers to a team of finance experts. This means that our customers, business owners across America, can 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

We are looking for an experienced leader in the Data Infrastructure and/or Analytics space to build out and scale Pilot’s data function. In this role, you will partner closely with all functions — ranging from Finance and Marketing to Product, Engineering, and Operations — to ensure that we can make data-driven decisions that help Pilot grow. This is a role with tremendous growth opportunity and potentially a wide scope; you will own Pilot’s Analytics infrastructure, build out a roadmap, and hire a team. For the right candidate, this could also include not just the Analytics function but the Engineering function as well. And Pilot’s data needs are often not that different from our customers’ needs — in this role you’ll have the opportunity to contribute to customer-facing financial insights features as well. If you are excited about democratizing data by extracting actionable insights and building scalable data pipelines, we would love to hear from you.
The responsibilities of this role include:
  • Define and execute Pilot’s analytics roadmap
  • Collaborate with cross-functional leaders to identify and prioritize the highest impact analytics initiatives
  • Manage our data warehouse so it can support data analysis and operational requirements from all teams
  • Automate reporting and visualization of key performance metrics in Looker
  • Drive operational excellence through optimization of data models
  • Document and improve our data framework so that all data can be connected and analyzed
  • Mentor and guide the professional and technical development of your team members. Help develop their careers, and assign them to projects tailored to their skill levels, personalities, work styles, and professional goals.
  • Either build an engineering team or work with an engineering team to provide the right scalable infrastructure and tooling for all teams at Pilot that need to consume data

About you

This role requires a blend of leadership and individual contributor responsibilities while we staff up our teams. As our ideal candidate, you will have 5+ years of hands on experience in a data analytics, business intelligence, or data engineering role, and you can demonstrate most the following:
  • Experience working with leadership to define and measure KPIs and other operating metrics
  • Experience leading and executing analytics initiatives in a fast-paced, high-growth environment
  • Great business intuition and strong project management skills
  • Experience hiring and managing high performing teams
  • Expert knowledge of SQL and relational databases (Snowflake is a plus, but you might know BigQuery, Redshift)
  • Experience building and maintaining data pipelines (we use Fivetran and Stitch currently)
  • Experience building reports and dashboards in Looker. Experience with other business intelligence tools such as Tableau, Mode, Periscope, Chartio are a bonus.
  • Experience with Salesforce, Zuora, and Marketo

About us

Pilot is about 135 people split across our San Francisco and Nashville offices. Our SF office is located right next to the Montgomery Street BART stop — though of course 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 engineering managers have a breadth of experience at companies of varying sizes. We invest in managers via peer mentorship forums 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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