[Hiring] Strategy and Planning Lead @Bask Health

Role Description

Bask is the best telehealth platform on the market. Our mission is to empower entrepreneurs and businesses to launch a DTC telemedicine company quickly and easily, abstracting away the complexities of the industry into an easy-to-use platform. With hundreds of features to meet the unique needs of telehealth, we put all the tools in our customers' hands for success.

We are a rapidly growing startup, and we work with care and intention to create a high-performance company with the following in mind:

• Speed Wins. Make decisions, move quickly, and know that if things go wrong, it's okay for you and the company.
• Intuition, Then Data. We're a data-driven company. We start with our instincts and then use data to validate our decisions and improve.
• Miles, Not Inches. Thinking small is a self-fulfilling prophecy. Favor bold ideas over incremental changes.
• Customer-Obsession. We are obsessed with helping all our customers launch multi-billion-dollar companies with ease.
• Ownership & Accountability, together. We embody a culture of extreme ownership, accountability, and teamwork.

A look into the day to day:

• Building and maintaining financial and operational models that connect revenue targets to hiring plans, team capacity, and business performance.
• Analyzing headcount, productivity, ramp time, and quota attainment to help leadership make informed investment decisions.
• Translating business goals into actionable plans, identifying gaps, and recommending opportunities to improve performance.

Qualifications

• A strategic thinker who loves working with numbers and understands how operational decisions drive business growth.
• Highly analytical, detail-oriented, and comfortable building models and frameworks from the ground up.
• Strong communicator who can translate complex analysis into practical insights for leadership and cross-functional teams.
• Comfortable working in a small, collaborative team where you'll wear many hats.
• Curious, self-aware, low ego, and extremely positive.

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.

What You'll Do

• Work AI-first: Use LLMs as your starting point to structure complex planning problems, build analytical frameworks, develop models, and draft recommendations.
• Build scalable planning models: Develop and maintain models that connect revenue targets to headcount, team capacity, productivity, and expected performance across the organization.
• Turn data into strategic decisions: Translate business goals into hiring plans, quota recommendations, resource allocation, and investment scenarios.
• Validate assumptions with real data: Work closely with Finance, Recruiting, Data & Analytics, and other teams to validate model assumptions.
• Improve how we plan: Identify opportunities to automate, simplify, and improve forecasting, reporting, and planning workflows.
• Build and maintain Bask's go-to-market capacity models, connecting headcount plans to revenue targets, expected attainment, and coverage requirements across Sales and supporting teams.
• Develop staffing and capacity frameworks to determine the appropriate ratio of supporting roles to sales representatives and business segments.
• Own productivity, ramp, attrition, and performance assumptions, using them to forecast future headcount requirements and evaluate investment scenarios.
• Partner with leadership on quota-setting methodology, including how revenue targets translate 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.
• Partner with Finance, Recruiting, and Data & Analytics to ensure planning models are accurate, assumptions are validated, and recommendations are grounded in reliable data.
• Build dashboards and reporting tools that give leadership visibility into business performance, resource allocation, and future planning needs.
• Find comfort in working in a fast-paced startup environment.
• Believe no task is too small and no task is too tall.