Job Description

Location(s)

We are hiring for this role to be based in the United States or Canada. This is a remote role unless you fall within the following parameters. If you live within approximately 50 miles of our San Mateo, CA or Provo, UT office, the position follows a hybrid schedule with in-office days on Mondays, Wednesdays, and Fridays.

About The Role

We are hiring our first Head of Self-Serve & Product-Led Growth to own and scale our self-serve / PLG revenue line. This is a high-ownership, quota-carrying role where you will grow the self-serve motion end-to-end. You will be responsible for ICP definition, strategy, experimentation, funnel optimization, cross-functional alignment, and execution. You will report to the CRO and work as a peer/partner with Product, Marketing, and Sales.
This is a large portion of current revenue, and we expect it will continue to be an area for high-growth and lead gen for future expansions. You must be comfortable with ambiguity, self-directed, creative in problem-solving, yet disciplined in creating repeatable structure as the motion matures. Ideal candidates have built or scaled self-serve/PLG motions before or have operated in fast-moving, high-stakes environments (startup, top-tier consulting, PE/VC portfolio ops)

What You'll Do

• Own the full self-serve P&L: carry and hit quarterly/annual revenue targets across sign-ups, activation, paid conversion, and expansion revenue.
• Design the self-serve GTM strategy ideal user profile, onboarding funnel, friction removal, pricing/packaging experiments, and growth loops.
• Run rapid experimentation: own A/B tests, cohort analysis, funnel optimization, and growth levers (paid acquisition, SEO/content, referral programs, Slack/Discord integrations).
• Cross-functional execution, partner with:
  • Partner daily with Product to influence roadmap (features that drive activation/expansion, self-serve onboarding UX, Slack bot, usage analytics).
  • Collaborate with Marketing to drive top-of-funnel acquisition (paid, organic, content, webinars/classes) and optimize handoff to self-serve.
  • Align with Sales on “healthy friction” rules (when to route to sales vs. keep self-serve) and use self-serve as a top-of-funnel engine for enterprise land-and-expand.
• Define success metrics (conversion rates, activation, expansion revenue, churn, LTV:CAC) and own weekly/monthly performance against goal.
• Build structured playbooks, conversion funnels, and automation (email, in-app messaging, onboarding sequences) that scale efficiently.
• Build Automations Transition from founder-led/scrappy execution → repeatable, semi-automated motion.

What You’ve Done

• Experience in AI, developer tools, or productivity SaaS.
• Background at top-tier consulting firm (McKinsey, BCG, Bain), PE/VC ops team, or early-stage startup founder/operator.
• Experience influencing product roadmaps for self-serve activation/expansion.
• Familiarity with AI and growth technology platforms

A Note On Pace

We’re building something new in a once-in-a-generation shift in technology and the legal industry, so we move at a relentless pace. We expect urgency, ownership, and good judgment even when things aren’t perfectly clear. If you need structure and consensus to do your best work, this isn’t the right place for you. If you thrive in ambiguity and growth, work with intensity, and want real responsibility, keep reading. We’re excited to meet you.

Compensation

GC AI's compensation package includes a competitive base salary and commission benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits. Our US-based compensation range for this role is: $300,000 – $350,000 OTE. Final offers may vary from the amount listed based on geography, candidate experience and expertise, and other factors.