The Company is entering an important phase of growth. It has meaningful customer relationships, an established broker ecosystem, a broad market opportunity, and significant opportunity to improve how it generates, converts, retains, and grows revenue.
We are seeking a Head of Revenue Operations to build and lead the operating system behind the Company's commercial organization.
This is not a traditional Sales Operations or CRM administration role. This individual will connect commercial strategy to execution across the full revenue lifecycle, from demand generation and broker engagement through pipeline, sale, onboarding, retention, renewal, and expansion.
The Head of Revenue Operations will establish the processes, data, systems, metrics, and management cadence that enable commercial teams to execute consistently and leadership to make better, faster decisions.
This is a highly visible, hands-on leadership opportunity for an experienced commercial operator who can bring structure and discipline to an evolving organization while maintaining a strong bias toward action.
What You Will Own
1. Build the Commercial Operating System
Create the infrastructure and management discipline required to drive predictable, profitable growth.
- Establish clear processes across the customer lifecycle, from opportunity creation through renewal and expansion.
- Define ownership, decision rights, handoffs, and service levels across Sales, Marketing, Channels, Account Management, Product, and Operations.
- Translate commercial priorities into measurable operating plans with clear owners, milestones, and outcomes.
- Establish weekly, monthly, and quarterly operating cadences for managing commercial performance.
- Create accountability for actions, decisions, risks, and commitments.
2. Create a Reliable View of the Revenue Engine
Give leadership a fact-based understanding of where growth is coming from, where performance is breaking down, and where intervention is required.
- Establish clear pipeline stages, definitions, exit criteria, and data requirements.
- Build visibility into pipeline coverage, conversion, velocity, win rates, and sales-cycle performance.
- Implement a consistent forecasting methodology and materially improve forecast accuracy.
- Establish performance visibility by seller, territory, segment, product, broker, and channel.
- Identify performance gaps and revenue risks early enough for management to act.
- Create a clear and consistent view of actual performance versus plan.
3. Make CRM and Commercial Data a Source of Truth
Build the data and systems foundation required to manage the commercial organization effectively.
- Own CRM governance, data standards, stage definitions, required fields, and adoption.
- Improve the quality and completeness of customer, broker, account, and opportunity data.
- Establish clear ownership and relationships across customers, brokers, opportunities, and territories.
- Integrate CRM, Finance, customer, and operational data where practical.
- Reduce manual reporting and individual-held knowledge.
- Build automated dashboards and scorecards for frontline leaders, executives, and the Board.
- Establish common definitions for the commercial metrics that matter.
4. Manage the Full Customer Lifecycle
Ensure Revenue Operations extends beyond winning new business to retaining and expanding existing customers.
- Create visibility from sale through onboarding, service, renewal, retention, and expansion.
- Strengthen handoffs between Sales, Account Management, Operations, and other customer-facing teams.
- Establish renewal calendars and customer-risk reporting.
- Build visibility into gross revenue retention, logo retention, at-risk revenue, cross-sell, and expansion.
- Identify revenue leakage and create mechanisms for earlier intervention.
5. Optimize Coverage, Capacity, and the Broker Channel
Help the organization deploy commercial resources against the highest-value opportunities.
- Support territory and account design using market potential, broker relationships, customer opportunity, and seller capacity.
- Establish clear ownership rules for accounts, opportunities, brokers, and territories.
- Build broker segmentation and tiering and create visibility into broker production, pipeline, conversion, activity, and opportunity.
- Partner with Finance and commercial leadership on capacity and productivity analysis.
- Model alternative coverage structures and quantify the expected economics.
- Provide the analytical foundation for decisions about commercial headcount and investment.
6. Strengthen Performance Management and Incentives
Create alignment between company objectives, individual accountability, and commercial incentives.
- Partner with Finance, HR, and commercial leadership on commercial compensation design and administration.
- Model quotas, attainment, payouts, and compensation economics.
- Establish reliable attainment and productivity reporting.
- Ensure compensation, territory ownership, opportunity crediting, and CRM data work together consistently.
- Support commercial leaders in establishing clear performance expectations and managing against them.
7. Turn Data Into Decisions
Revenue Operations should not simply produce reports. It should help the organization make better decisions.
- Develop the core commercial scorecard used to manage the business.
- Establish baselines and targets for the key drivers of revenue performance.
- Analyze performance by customer segment, product, broker, territory, channel, and cohort.
- Partner with Finance on revenue, retention, margin, and unit economics.
- Build business cases for commercial investments and growth initiatives.
- Establish clear measures of success before pilots and initiatives are scaled.
What Success Looks Like
During the first 90 days, the Head of Revenue Operations will establish the foundations of a disciplined commercial operating system, including:
- A clean, credible pipeline with standardized stages and exit criteria.
- A consistent weekly pipeline and forecasting cadence.
- Material improvement in CRM data quality and adoption.
- A commercial scorecard used by leadership to manage the business.
- Clear account, broker, opportunity, and territory ownership.
- Baseline performance metrics across the commercial organization.
- Clear ownership and handoffs across the customer lifecycle.
- Visibility into renewals, retention, and customer revenue risk.
- Reduced dependence on manual reporting and individual-held knowledge.
Over time, success means the organization can confidently answer, with supporting data:
- Where is growth coming from?
- Where is the revenue engine breaking down?
- Which brokers, channels, segments, and sellers are creating value?
- Where is revenue at risk?
- What commercial capacity do we need?
- Where should we invest the next dollar to drive profitable growth?
Key Measures
The Head of Revenue Operations will establish and manage a common commercial measurement framework. Key measures will include:
- Pipeline coverage, quality, conversion, and velocity.
- Win rate and sales-cycle length.
- Forecast accuracy.
- Quota attainment and seller productivity.
- CRM completeness and adoption.
- Lead source and attribution.
- Broker activation, production, and conversion.
- New business by segment, broker, and channel.
- Gross revenue retention and logo retention.
- At-risk revenue and revenue recovered.
- Renewal performance.
- Cross-sell and expansion.
- Customer onboarding and handoff performance.
The specific measures will evolve as the commercial operating system matures. The objective is not to create more reporting. It is to identify and consistently manage the measures that drive performance.
What We're Looking For
We are looking for a commercial operator and builder, not simply a reporting, analytics, or systems specialist.
The ideal candidate will bring:
- 8+ years of experience in Revenue Operations, Sales Operations, Commercial Operations, or a related discipline, including meaningful leadership responsibility.
- Experience building or materially upgrading RevOps capabilities in a growing or transforming business.
- Strong command of CRM, pipeline management, forecasting, commercial analytics, and performance management.
- Demonstrated ability to turn incomplete or messy data into useful management information and action.
- Experience designing commercial processes across multiple functions rather than optimizing Sales in isolation.
- Strong financial and analytical skills, including territory, capacity, quota, productivity, and compensation modeling.
- Ability to operate credibly with senior executives while remaining highly hands-on.
- Experience creating adoption and accountability across functions without relying on formal authority.
- Strong judgment about what information and processes actually improve performance versus simply adding complexity.
- A bias toward action, simplification, accountability, and measurable outcomes.
Experience in benefits administration, HR technology, insurance, employee benefits, broker-distributed businesses, or another B2B environment with meaningful channel complexity is highly desirable.
The Profile
The right person for this role can move comfortably between strategy and execution.
One day, you may be working with the CEO and CFO on the commercial scorecard. The next, you may be challenging a forecast with a sales leader, working through broker segmentation, fixing a broken customer handoff, redesigning CRM workflows, or building the analysis behind a territory or investment decision.
You will thrive in this role if you are:
- A Builder: You create operating systems rather than simply inherit them.
- Commercial: You understand how revenue is actually generated, converted, retained, and expanded.
- Analytical: You use data to expose problems, prioritize action, and improve decisions.
- Hands-on: You are willing to work at both the strategic and detailed levels.
- Cross-functional: You connect Sales, Marketing, Channels, Account Management, Finance, Product, and Operations around common outcomes.
- Accountability-oriented: You believe every important commercial outcome should have an owner, a number, and a cadence.
- Pragmatic: You build the infrastructure required to improve performance now and scale it as the business grows.
- Action-oriented: You do not wait for perfect information before making progress.
Why This Role Matters
The Company's opportunity is not simply to sell more. It is to build a commercial engine that can produce predictable, sustainable, and profitable growth.
The Head of Revenue Operations will be one of the key architects of that engine.
This individual will create the visibility, discipline, processes, and infrastructure that allow teams to execute consistently, leadership to intervene quickly when performance is off track, and the organization to invest in growth with confidence.
CONFIDENTIAL — This position description is intended for use in a confidential executive search process. Company identity and additional organizational details will be shared with qualified candidates at the appropriate stage of the process.
