Strategy and Planning Lead - Billing/Revenue

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. We accomplish this by knowing our customers incredibly well and finding ways to make their businesses better.
• Ownership & Accountability, together. We embody a culture of extreme ownership, accountability, and teamwork. We count on every team member to take responsibility for their work, embrace a proactive mindset to overcome challenges, and work together to achieve our collective success.

• 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.

A strategic thinker who loves working with numbers and understands how operational decisions drive business growth. You are highly analytical, detail-oriented, and comfortable building models and frameworks from the ground up. You can take complex business questions, break them down into manageable problems, and turn your findings into clear recommendations.

You are a self-starter who thrives in ambiguity and enjoys solving problems that don't always have an obvious answer. You take ownership of your work, think several steps ahead, and are comfortable challenging existing assumptions when the data points in another direction. You are a strong communicator who can translate complex analysis into practical insights for leadership and cross-functional teams.

You are comfortable working in a small, collaborative team where you'll wear many hats. You are curious, self-aware, low ego, and extremely positive. You believe no task is too small and no task is too tall.

Revenue Operations at Bask Health is AI-first and customer-obsessed. Work starts in an LLM to clarify intent and context, moves into research, modeling, and analysis, is validated against real business data and operational outcomes, and is continuously refined as we learn. AI and self-serve research are default parts of the workflow, not side experiments.

We are looking for Revenue Operations people who take full ownership of strategic planning, treat AI as a real collaborator, and care deeply about building the analytical foundations that help Bask scale.

• Work AI-first: Use LLMs as your starting point to structure complex planning problems, build analytical frameworks, develop models, and draft recommendations. Apply your own judgment to validate outputs and turn them into reliable, decision-ready work.
• 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. Help leadership understand the trade-offs behind different growth strategies.
• Validate assumptions with real data: Work closely with Finance, Recruiting, Data & Analytics, and other teams to validate model assumptions, monitor performance, and ensure planning decisions reflect actual business conditions.
• Improve how we plan: Identify opportunities to automate, simplify, and improve forecasting, reporting, and planning workflows. Share effective AI-native workflows, prompts, and models across Revenue Operations so we raise the bar together.

• 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. Identify gaps early and model their potential business impact.
• 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.

• 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.