Strategy and Planning Lead

Bask Health

About The Position

Bask is hiring a Strategy and Planning Lead for its Revenue Operations function. The role owns strategic planning and the analytical foundations that support Bask’s growth, with an AI-first approach to research, modeling, analysis, and recommendations. The person in this role will build and maintain go-to-market capacity and financial models that connect revenue targets with headcount, team capacity, productivity, quota attainment, and expected performance across Sales and supporting teams. The role translates business goals into hiring plans, quota recommendations, resource allocation, and investment scenarios. It evaluates staffing ratios, ramp and attrition assumptions, pipeline coverage, leading indicators, and performance benchmarks; tracks plan versus actual results; and helps leadership understand gaps and trade-offs. The Strategy and Planning Lead also develops quarterly planning deliverables and dashboards, validates assumptions with Finance, Recruiting, Data & Analytics, and other teams, and improves forecasting, reporting, and planning workflows. The ideal candidate is analytical, detail-oriented, comfortable building models and frameworks from the ground up, and able to turn complex questions into clear, practical recommendations. They thrive in ambiguity, take ownership, communicate well across teams, and enjoy building scalable systems in a fast-paced startup environment. AI and self-serve research are default components of the workflow; candidates are expected to use LLMs as collaborators while applying judgment to validate their outputs.

Requirements

At least 6 years of experience in Revenue Operations, Sales Operations, Strategic Finance, 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, including the ability to build complex models from scratch and explain their assumptions.
Strong understanding of revenue planning, sales productivity, pipeline coverage, and business performance metrics.
Excellent Excel or Google Sheets skills, including experience building sophisticated models and analyzing large datasets.
Experience working cross-functionally with Finance, Recruiting, Sales, and Data & Analytics teams.
Comfort operating with ambiguity and building structured solutions from incomplete information.
Strong written and verbal communication skills, including the ability to explain complex analysis and strategic recommendations clearly.
Highly organized, with the ability to manage multiple projects and priorities in a fast-paced environment.
Independent, motivated, and able to take ownership while seeking help when needed.
Creative problem-solving ability and determination to succeed.
Builder’s mindset, with an interest in creating scalable frameworks, models, and systems.

Nice To Haves

Experience with SQL, BI tools, or data visualization platforms.
Experience using LLMs and AI-native workflows for research, modeling, and analysis.

Responsibilities

Build and maintain go-to-market capacity models that connect headcount plans to revenue targets, expected attainment, and coverage requirements across Sales and supporting teams.
Develop staffing and capacity frameworks to determine appropriate ratios of supporting roles to sales representatives and business segments.
Own productivity, ramp, attrition, and performance assumptions; use them to forecast headcount requirements and evaluate investment scenarios.
Partner with leadership on quota-setting methodology, including translating revenue targets into achievable quotas and appropriate ramp expectations.
Analyze pipeline coverage requirements, leading performance indicators, and activity benchmarks needed to support revenue goals.
Build and maintain 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 their potential business impact.
Partner with Finance, Recruiting, Data & Analytics, and other teams to validate assumptions and ensure planning recommendations use reliable data.
Build dashboards and reporting tools that provide leadership visibility into business performance, resource allocation, and future planning needs.
Use LLMs to structure planning problems, develop analytical frameworks and models, and draft recommendations; validate outputs using judgment and real business data.
Identify opportunities to automate, simplify, and improve forecasting, reporting, and planning workflows.
Share effective AI-native workflows, prompts, and models across Revenue Operations.
Translate business goals into actionable plans and recommendations for improving performance.
Communicate complex analysis and strategic recommendations clearly to leadership and cross-functional teams.