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


  • Provide timely technical support to all internal stakeholders
  • Design and implement processes to ensure efficient IT operations


  • Support
    • Establish and manage an IT helpdesk to support all staff
    • Provide IT troubleshooting support for all staff
    • Train staff on newly installed hardware & software systems
  • Hardware 
    • Purchase & provision computers and other IT equipment for internal use 
    • Manage peripheral equipment and expendable supplies
    • Responsible for the life-cycle maintenance of all IT equipment, including repairs and remote management
    • Execute all IT tasks including equipment configuration & training for all new hires 
    • Execute all IT tasks related to off-boarding terminated employees including overseeing equipment return
    • Conduct recertification and reissue of all IT equipment
    • Maintain AV equipment 
  • Software
    • Install, administer and maintain multiple software systems
    • Execute on the evaluation, analysis, recommendation and purchase of all  software used company-wide
    • Develop enterprise-level protocol for the purchase of/subscription to all IT software 
    • Manage internal software subscriptions including renewals and upgrades
    • Troubleshoot network and software issues 
    • Ensure security software is kept up to date
  • Systems
    • Review all systems currently in use and develop a recommendation to produce optimal results 
    • Responsible for administering all systems groups including company email groups 
    • Set protocol for, and manage access control of, all corporate IT systems
    • Manage and troubleshoot Network connectivity
    • Oversee corporate Network infrastructure
    • Ensure the security of all IT systems by performing backups and updating security protocol
    • Conduct inspections to ensure IT systems and equipment are operational
  • General
    • Document all IT processes and protocol
    • Provide advice and recommendations to management on processes and techniques required for improved work operations
    • Collaborate with internal stakeholders to achieve set objectives
    • Conduct surveys and research to identify areas that require improvement and ways to achieve desired improvement
    • Collaborate with internal stakeholders to identify their requirements and ensure the service/products they receive meet and exceed their expectations

Experience & Qualifications

  • Significant experience overseeing the IT function at a tech company 
  • Minimum 5 years’ experience in corporate IT technical support
  • Extensive knowledge of computer systems, including Mac, Windows, wired/wireless networking, and computer security
  • Ability to manage multiple projects simultaneously
  • Strong communication skills
  • Ability to troubleshoot complex software and hardware issues

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

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