Strategy and Planning Lead – Billing/Revenue

Posted 15hrs ago

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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.