Head of RevOps

About Liberate

Liberate builds AI agents to automate manual work for the $2.7 trillion insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance carrier and broker operations. We've raised $82M to date, including a $50M Series B in October 2025, backed by top-tier venture firms. Today our agents run millions of automated transactions a month across enterprise carriers, brokers, and agencies, resolving calls, emails, and SMS end-to-end and writing back to the core systems of record. We're insurance people building AI, and that operator DNA is why customers trust us with their highest-volume operations.

About the Role

As Liberate scales from early traction into a repeatable, predictable revenue engine, we're looking for a Head of Revenue Operations to build and run the GTM plumbing underneath it. You'll own the entire revenue cycle end-to-end — territory design, pipeline hygiene, forecasting, metrics and KPIs, and the systems and behaviors that keep the whole engine honest. This is a builder's role, not a caretaker's. You'll design the geo and segment territory model, define the metrics that tell leadership the truth about the business, and put real teeth behind data hygiene — building the rules, automations, and accountability structures that keep the CRM clean at the source rather than inspecting it after the fact. You'll report to the CRO and work directly with Sales, Marketing, and CX leadership.

What You'll Do

• You will own the revenue cycle end-to-end including territory design, capacity planning, quota setting, forecasting, pipeline management, and compensation administration; you are accountable for the full motion from pipeline creation through renewal and expansion. You will build and maintain geo and segment territories by designing territory and account-scoring models that align coverage with opportunity and evolve them as the business grows into new geos and segments. You will define and own the metrics that run the business, establishing a single source of truth for pipeline coverage, conversion by stage, velocity, win rate, ARR and NRR, CAC, and rep productivity, with consistent definitions across Sales, Marketing, and CX. You will make pipeline hygiene a system, not a task, by building rules, automations, and accountability structures in partnership with sales leadership that keep CRM data clean and trustworthy at the source and enforce the behaviors that maintain it. You will own the GTM plumbing by administering and evolving the revenue tech stack, including CRM, marketing automation, analytics, and AI and automation layers, ensuring clean, synchronized data flows across every system of record. You will run the executive operating cadence, including forecast calls, pipeline reviews, QBRs, and board-level reporting, with the rigor and consistency that lets leadership make fast, confident decisions. You will default to AI-first workflows by identifying where AI tools can replace manual reporting, forecasting, and analysis work and building the case for adoption with measurable outcomes such as time saved and accuracy improved. You will partner cross-functionally, working closely with Sales, Marketing, CX, and Finance leadership to drive one shared set of definitions, one operating rhythm, and consistent execution against company objectives.

• What We're Looking For

• Must Have: 10+ years in Revenue Operations, Sales Operations, or GTM Strategy, ideally in B2B SaaS, with a track record of building the operating rhythm and data infrastructure for a scaling revenue organization. Deep, hands-on experience owning the full revenue cycle including territory design, quota setting, forecasting, pipeline management, and compensation administration. Proven ability to build and enforce pipeline hygiene and data discipline, creating guardrails and incentives that keep CRM data clean, not just dashboards that report on it. Hands-on experience with AI-first GTM tools such as Cursor, HubSpot, and Clay for AI-powered enrichment and prospecting, along with fluency using tools like Claude to automate reporting, analysis, and coaching workflows. Strong analytical and storytelling skills to turn a messy dataset into an executive-ready narrative. Comfortable operating at both strategic levels with executives and the board and in the weeds with reps and managers.

• Nice to Have: Experience in AI-native or Voice AI companies, or exposure to insurance, fintech, or another regulated industry. Background at a high-growth, venture-backed startup where you built process rather than inherited it.

• What Success Looks Like

• Leadership and the board trust the numbers because the definitions, the data, and the process behind them are consistent and clean. Reps and managers operate inside a clear, enforced operating rhythm where territory, quota, forecast, and pipeline hygiene are systems rather than quarterly scrambling. AI-first tools handle manual reporting and analysis, freeing the team to focus on judgment and strategy. Liberate's GTM engine scales cleanly into new geos, segments, and product lines without the plumbing breaking.

• Compensation & Benefits

• Target compensation: $200,000 - $220,000 base, plus equity and variable. Final offer depends on level, experience, and location. Competitive salary with equity options. Comprehensive health, dental, and vision insurance. 401(k) plan. Flexible PTO. Flexible, hybrid work environment out of our Bay Area office. Collaborative, high-ownership company culture.