What we’re building
Pilot is a tech company building the bookkeeping firm you wish existed. We deliver books and a customer experience of unparalleled quality by automating the boring stuff and equipping a team of finance experts with software superpowers to deftly handle the rest.
 
The team
We are a small but passionate team of 140+ based in San Francisco and Nashville. Pilot’s seasoned founding team has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox). We give our employees a lot of responsibility and ownership of their work, and we hire people from a very wide range of backgrounds and experience. Our team members operate with a high degree of empathy for our customers and each other.
 
The role
We are looking for someone to oversee Pilot’s billing experience, ranging all the way from the mechanics of how customers sign up for Pilot’s products through to how Pilot collects cash and recognizes revenue.   At our current scale, our billing system processes tens of millions of dollars per year and in not long we expect to be processing over $100M per year.   We leverage best-in-class third party software for powering our billing system, so this role requires sound judgment in managing and adapting that system rather than doing software development.  This role reports to Pilot’s COO/cofounder and will have significant business impact, working with leaders from across many functions at Pilot.
  
Key responsibilities
  • Learn the details of Pilot’s billing system from Pilot’s COO/cofounder, who currently maintains that system, becoming the first person on and leader of Pilot’s dedicated billing team
  • Work with executive leadership on defining how new offerings will work from a customer billing experience perspective 
  • Work with Pilot’s sales team on how orders are placed via the billing system
  • Work with Pilot’s controller and accounting team on how revenue is recognized via the billing system
  • Work with Pilot’s analytics team and strategic finance team on how business decisions are made based on billing system data
  • Support and help resolve issues related to Pilot’s billing system, with both internal stakeholders and customers
  • Contribute to Pilot’s thinking on how we should adapt how our products are sold (ranging from the customer billing experience to pricing & packaging), based on data and experience
 
 About you
  • 4+ years of experience, including some experience either as a technical product manager or software engineer
  • Sufficiently technical to write (and debug, as necessary) software configuration files
  • Experience working in a fast-growing environment
  • High level of autonomy and sound judgment
  • Strategic thinker who can also execute on tactical necessities — no task is too large or too small
 
Benefits of working at Pilot
  • Medical, dental, and vision benefits
  • Holidays and flexible PTO
  • Paid family leave
  • Company sponsored 401(k) plan
  • Pre-tax commuter benefit
  • Convenient office location in San Francisco, close to the Montgomery BART station (although currently the company is WFH due to COVID)

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