ContentFly (YC W21) is one of the fastest growing B2B startups in the world and aims to make content marketing easy and effective for businesses. We’ve grown to nearly $4m ARR in a year with a small team, no sales or dedicated marketing. We just closed a $10m Series A with Tier 1 funds like Khosla Ventures & YCombinator.

The Head of People role is a critical asset that will be directly responsible for the People function (including recruiting, organizational planning, learning and development, career progression and compensation, benefits management, employee relations and engagement, and various cultural initiatives). You will develop and champion strategies and implement programs that inspire, and motivate our employees.

You’ll be employee #26. Excited to help grow and cultivate an incredible team from 26 to 250 and beyond? Let’s talk.


  • Work alongside marketing to build our employer brand and position us as a leading employer in the North American Tech ecosystem
  • Lead and build our recruitment efforts and perform end to end talent acquisition across the organization
  • Build and own our recruiting, pre-boarding, and onboarding experience of new hires
  • Build and own our company-wide performance and development program
  • Plan in advance the work streams and roles needed to set the company up to scale to hundreds of employees
  • Ensure compliance with each country’s employment laws and regulations as well as those of the U.S. (federal, state, local)
  • Lead the management of day-to-day employee matters and advise management and staff regarding employee relations, policies, and other areas across HR
  • Oversee our HRIS management, legal matters, payroll, and benefits program
  • Own and define our company culture, including Core Values and Core Competencies
  • Oversee our office and asset management including tooling, expenses, hardware, etc.



  • 5 – 7 years of experience in HR/People & Culture with at least 2 years at an executive/leadership level.
  • Strong working knowledge of foundational employment laws and practices – both in Canada and in the USA
  • You have helped to scale a company from 20 to 500 and can make recommendations based on real-life experience
  • 2-4 years’ experience working in a fast-growing, venture-backed tech startup (SaaS strongly preferred)
  • Experience building, leading and developing a team
  • Experience leading complex workstreams
  • Familiarity with People Ops processes and systems
  • Consistent success and career progression


Why you should join ContentFly

  • Above market salary + options
  • Unlimited vacation/PTO
  • Fully remote & distributed
  • Free laptop + home office budget
  • Physical + mental health budgets
  • We’ll fly you around the world multiple times a year to hang out with the team in interesting places