Strategy and Planning Lead – Billing/Revenue
Posted 15hrs ago
Employment Information
Report this job
Job expired or something wrong with this job?
Job Description
Revenue Operations Lead building capacity, quota, and headcount models for Bask, a telehealth platform enabling DTC telemedicine businesses. Driving AI-first planning and strategic growth decisions.
Responsibilities:
- Build and maintain financial and operational models connecting revenue targets to hiring plans, team capacity, and business performance.
- Analyze headcount, productivity, ramp time, and quota attainment to inform leadership investment decisions.
- Translate business goals into actionable plans, identify gaps, and recommend performance improvements.
- Use LLMs to structure planning problems, build analytical frameworks, develop models, and draft recommendations, validating outputs with business judgment and real data.
- Develop go-to-market capacity models linking headcount plans to revenue targets, expected attainment, and coverage requirements across Sales and supporting teams.
- Develop staffing and capacity frameworks for supporting-role ratios across sales representatives and business segments.
- Own productivity, ramp, attrition, and performance assumptions to forecast headcount requirements and evaluate investment scenarios.
- Partner with leadership on quota-setting methodology and ramp expectations.
- Analyze pipeline coverage requirements, leading indicators, and activity benchmarks supporting revenue goals.
- Build quarterly planning deliverables, including quota recommendations, headcount plans, capacity models, and investment proposals.
- Track plan-versus-actual performance across headcount, capacity, productivity, and quota attainment; identify gaps and model business impact.
- Partner with Finance, Recruiting, and Data & Analytics to validate assumptions and ensure accurate planning models.
- Build dashboards and reporting tools providing visibility into business performance, resource allocation, and future planning needs.
- Improve forecasting, reporting, and planning workflows through automation and simplification.
- Share effective AI-native workflows, prompts, and models across Revenue Operations.
Requirements:
- 6+ years of experience in Revenue Operations, Sales Operations, Strategic Finance, Financial Planning & Analysis (FP&A), or a similar analytical role within a high-growth SaaS company.
- Proven experience building and maintaining headcount, capacity, productivity, or resource allocation models tied to revenue targets.
- Experience with quota-setting, sales ramp modeling, and go-to-market planning.
- Advanced financial modeling and analytical skills, with the ability to build complex models from scratch and explain the assumptions behind them.
- Strong understanding of revenue planning, sales productivity, pipeline coverage, and business performance metrics.
- Excellent Excel or Google Sheets skills, with experience building sophisticated models and analyzing large datasets.
- Experience with SQL, BI tools, or data visualization platforms is a plus.
- Experience working cross-functionally with Finance, Recruiting, Sales, and Data & Analytics teams.
- Comfortable operating with ambiguity and building structured solutions from incomplete information.
- Creative problem solver with a determination to succeed.
- Independent and motivated, with the wisdom to seek help where needed.
- Highly articulate, able to communicate complex analysis and strategic recommendations clearly in writing and in person.
- Highly organized, with the ability to manage multiple projects and priorities in a fast-paced environment.
- A builder's mindset: you enjoy creating frameworks, models, and systems that can scale rather than relying on existing processes.




















