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Ent is an intent-aware workspace security platform protecting human and AI-driven work. Founded by the co-founders of RiskIQ (acquired by Microsoft) and the team behind Microsoft Security Copilot, Ent is in production with Global 2000 customers across hospitality, financial services, and defense, backed by top-tier investors including Sequoia and In-Q-Tel.
You will be Ent's first dedicated Head of Revenue Operations, reporting to the CRO. This is a hands-on role building the operating system underneath the go-to-market function from the ground up. You'll own the revenue operating model, GTM systems roadmap, planning mechanics, and operational cadence that drive predictable, scalable growth.
Key responsibilities include:
- Building the revenue operating model: unified definitions of accounts, opportunities, and stages; clean data by default; and workflows across pipeline management, forecasting, and customer lifecycle.
- Deploying AI across the revenue workflow (data hygiene, call/deal summarization, forecast signals, renewal risk, self-serve reporting) and articulating ROI.
- Transitioning from reactive reporting to real-time revenue intelligence with predictive forecasting, leading indicators for expansion/churn, and scenario modeling.
- Owning the GTM systems roadmap (CRM, marketing automation, sequencing, conversation intelligence, enrichment, CS, analytics) and rationalizing the stack.
- Integrating HubSpot and Gong as one system with call and deal signal flowing into CRM, reporting, and AI workflows.
- Standing up deal desk with pricing guardrails, approval paths, and quote-to-cash processes in partnership with finance.
- Building planning mechanics: territory and quota models, capacity plans, headcount scenarios, and commission administration.
- Creating multi-level reporting (rep, frontline manager, CRO, board) that reconciles to the same numbers.
- Building operational rigor under sales development: BDR activity/conversion reporting, sequencing, routing, capacity, and ramp models.
- Running the operating cadence (weekly pipeline inspection, forecast calls, QBRs) with trustworthy rigor.
- Partnering with sales leadership and product marketing on enablement through scorecards, call/deal analytics, and productivity data.
REQUIREMENTS (Must-Haves):
- Built AI into a sales organization's tooling and can articulate ROI in numbers. Hands-on experience with Claude or comparable model tooling required. Must demonstrate what was built (agents, automations, LLM-powered workflows), what it replaced, adoption, and measurable returns (hours, cost, cycle time, conversion).
- Built reporting for every level of a sales organization (rep, frontline manager, executive, board) and understand how each level needs the same data presented differently.
- Owned HubSpot and Gong (or close equivalents) and integrated them: data model, sync, call and deal signal, and troubleshooting drift.
- Had sales development in scope (BDR/SDR operations, reporting, routing, capacity) and partnered with the leader running that team.
- Led a tool rationalization: inherited state, consolidations/eliminations, retained tools and rationale, cost before/after, and team adoption strategy.
- Owned revenue or GTM operations through a startup's fast-growth phase and can point to the specific stretch scaled through and systems/processes built at each stage.
- Run deal desk or owned pricing, approval, and quote-to-cash for enterprise deals, working closely with finance and legal.
- Built planning artifacts: territory and quota models, capacity plans, commission calculations that survived audit and sales team verification.
- Fluent in data: can build models, write queries, and defend numbers in the room. This is a hands-on building role initially.
BONUS:
- First revenue operations hire somewhere who built the function from scratch.
- Supported enterprise security or infrastructure sales motion selling to CISOs and technical buyers.
- Migrated a CRM or consolidated onto a HubSpot-centered stack.
- Operationalized a pricing/packaging change, product launch, or international expansion.
- Owned renewals and expansion reporting, not just new business.
