Head of Revenue Operations

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

• Own the revenue cycle end-to-end. Territory design, capacity planning, quota setting, forecasting, pipeline management, and comp administration — you're accountable for the full motion from pipeline creation through renewal and expansion.
• Build and maintain geo and segment territories. Design territory and account-scoring models that align coverage with opportunity, and evolve them as the business grows into new geos and segments.
• Define and own the metrics that run the business. Establish a single source of truth for pipeline coverage, conversion by stage, velocity, win rate, ARR/NRR, CAC, and rep productivity — with consistent definitions across Sales, Marketing, and CX.
• Make pipeline hygiene a system, not a task. Build the 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 keep it that way.
• Own the GTM plumbing. Administer and evolve the revenue tech stack (CRM, marketing automation, analytics, and AI/automation layers), ensuring clean, synchronized data flows across every system of record.
• Run the executive operating cadence. Forecast calls, pipeline reviews, QBRs, and board-level reporting — with the rigor and consistency that let leadership make fast, confident decisions.
• Default to AI-first workflows. Identify where AI tools can replace manual reporting, forecasting, and analysis work, and build the case for adoption with measurable outcomes — time saved, accuracy improved, pipeline impact — not adoption for its own sake.
• Partner cross-functionally. Work 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 org.
• Deep, hands-on experience owning the full revenue cycle: territory design, quota setting, forecasting, pipeline management, and compensation administration.
• Proven ability to build and enforce pipeline hygiene and data discipline — you build the guardrails and incentives that keep CRM data clean, not just the dashboards that report on it.
• Hands-on experience with AI-first GTM tools — e.g., Cursor, HubSpot, and Clay for AI-powered enrichment and prospecting — along with general fluency using tools like Claude to automate reporting, analysis, and coaching workflows.
• Strong analytical and storytelling skills — you can turn a messy dataset into a clear, executive-ready narrative.
• Comfortable operating at both altitudes: strategic planning with executives and the board, and detailed, in-the-weeds problem solving 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 — territory, quota, forecast, and pipeline hygiene are systems, not once-a-quarter scrambles.
• AI-first tools are doing the manual reporting and analysis work, 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