Remote Head of Support job at Pilot

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Pilot (YC W17) is looking for an experienced Head of Support to join our rapidly-growing team on a mission to create a more open worldwide job market. 

A bit about who we are

Pilot helps companies handle payroll, benefits and compliance for their remote teams. We believe that your opportunities in life shouldn’t be dictated by where you’re from or where you happen to live, and we’re helping our customers live by that too. We’re a team of 16 backed by Sam Altman, Y Combinator, Credo Ventures, Automattic, Kyle Vogt and many other amazing investors.

What you will be working on

As the Head of Support you will make sure we provide high-class customer support and ensure our customers’ experience with Pilot is exceptional. You will:
  • Lead a team of customer support specialists distributed across different countries and time zones. You’ll be responsible for expanding the team as the company grows.
  • Review and improve our support OKRs and make sure the team meets their goals
  • Gather, analyze and present support metrics and data during quarterly business reviews
  • Collaborate closely with product, finance and sales teams to ensure commonly reported issues are resolved in the most effective way
  • Manage support tools and implement better solutions as the team scales
  • Handle escalations and solve the most challenging issues
  • Look after the most demanding customers and proactively help them get the most out of Pilot
  • Be on top of all the product changes and make sure our knowledge base is up to date 
  • Be responsible for building and shaping our Help Center 


  • Experience building and leading distributed support teams. Proven track record in scaling teams and maintaining high quality support.
  • Experience providing users with product support
  • Amazing communication skills, both verbal and written
  • Proficiency in English
  • Strong work ethic and ability to work without supervision. You are autonomous, self-managed, and proactive.
  • You are reliable, hardworking, and keen to dive in and get your hands dirty. There is no task too menial for you.
  • Availability to jump on a call with team members based in Brazil, Philippines and Europe.

We’d especially like to talk to you if

  • You have experience and desire to work in a distributed environment
  • You speak Portuguese or Spanish
  • You have domain knowledge in international hiring, international payments or payroll


  • Annual salary from $23,600 to $34,000 and up to 0.025% of equity
  • Unlimited vacation policy
  • Ability to work remotely from anywhere in the world
    • We try to hold all most of our team meetings between 7am–9am PST / 3pm–5pm BST / 11pm–1am JST to accommodate as many time zones as possible

Job posted 2021-04-14