Senior Director of Revenue Strategy & Operations, Spring Health

• 12+ years of experience in Revenue Operations, Sales Strategy, Business Operations, Consulting, or a related function at a high-growth B2B SaaS or technology company
• 5+ years of people management experience, with a track record of developing high-performing teams and evolving team capabilities in response to changing business needs
• Deep expertise in GTM planning, including annual planning, quota design, territory modeling, headcount planning, and long-range strategic planning
• Hands-on experience designing and administering variable compensation programs — including plan architecture, commission modeling, payout accuracy, and field communication
• Strong analytics fluency, including proficiency with Looker (or equivalent BI tools such as Tableau or Sigma) for building dashboards, data models, and self-serve reporting infrastructure
• Advanced SQL skills or experience working alongside analytics engineering teams to define and validate data models
• 2+ years of demonstrable experience designing and deploying automation, AI, and/or ML systems in a GTM context (prospecting, forecasting, coaching, data enrichment - to automate workflows, accelerate analysis, and build productivity into operational processes
• Proven ability to lead cross-functional strategic initiatives with executive-level stakeholders and to distill complex data into clear, actionable recommendations
• Experience as an operational partner to segment or business unit leaders, translating business performance data into strategic recommendations and enabling field execution
• Research shows that women and people from historically underrepresented communities often hesitate to apply for roles unless they meet every qualification compared to other similarly-qualified candidates. At Spring Health, we are committed to fostering a workplace where everyone feels valued, empowered, and supported to Thrive. If this role excites you, we encourage you to apply

Desirable

• Reporting to the Vice President of Revenue Operations and sitting on the Revenue Operations leadership team, the Senior Director of Revenue Strategy & Operations is the strategic and operational engine of our go-to-market organization
• This individual will own annual and long-range planning, variable compensation strategy and execution, and a team of Field Operations leaders who are deeply embedded with our segment leaders across the business
• What makes this role distinct is its mandate as the AI orchestration layer of our AI-native RevOps organization - this leader will architect how people, processes, data, and AI agents work together to drive productivity at scale
• This is a full time, remote position on our team. Quarterly travel is required for team/company events or meetings
• Lead annual and long-range planning (LRP) end-to-end — from capacity modeling and quota design to territory architecture and headcount alignment — translating company growth targets into executable GTM plans
• Drive rigorous forecast cadence and scenario planning, partnering with Finance, Sales, and Customer Success leadership to deliver predictable revenue outcomes and clear business visibility to the executive team
• Architect and own a portfolio of strategic projects and cross-functional initiatives, acting as a trusted operator and thought partner to the CRO and revenue leadership team
• Own and execute the Revenue operating cadence and rhythm across forecasting, pipeline, strategic deal reviews, and more
• Own the end-to-end variable compensation strategy, design, and execution across the revenue organization — including plan design, modeling, and administration — ensuring incentive structures are competitive, aligned to business outcomes, and clearly understood by the field
• Partner with Finance, People, and Sales leadership to model compensation scenarios, run pay equity analyses, and evolve comp plans in response to market and business changes
• Lead and develop a team of Field Operations partners embedded with segment leaders across the business — evolving their role from operational executors to AI-enabled strategic builders who develop analytics, dashboards, and AI agents in the field, while also being strong strategic and operational partners to our leaders across sales, CS, and partnerships
• Ensure Field Operations leaders serve as full-stack partners to their segments: owning business reviews, pipeline hygiene, performance insights, and the build-out of Looker dashboards and AI-powered workflows that accelerate their segments' productivity
• Serve as the AI orchestration layer for Revenue Operations — defining how AI is adopted within the various segments and how the team deploys AI agents, automation, and analytics tools (including Claude and Looker) across people, process, and data to compound team productivity and decision-making velocity
• Scale an AI-native operating model for our field teams: establishing standards for prompt engineering, agent deployment, and tool integration; measuring and improving AI productivity gains through; writing end user requirements for underlying data sources and semantic layers as well as for agentic workflows
• Champion a culture of continuous experimentation and tooling adoption, identifying where AI can eliminate repetitive work, surface insights faster, and enable the team to operate at a level beyond headcount - this means you and your teams are experimenting daily
• What success looks like:
• Planning quality and timeliness: Annual plan and LRP delivered on schedule, with quota attainment rates and ramp-to-productivity metrics tracking at or above industry benchmarks across all segments. Quotas and compensation plans in hand at the start of the fiscal year
• Variable compensation accuracy and satisfaction: Compensation plans are administered accurately (< 1% dispute rate), delivered on time, and score favorably on field satisfaction surveys
• Revenue forecast accuracy: Segment and company-level forecasts fall within ±5% of actuals on a rolling 90-day basis, reflecting strong operational rigor across the Field Operations team
• AI productivity impact: Measurable and documented productivity gains from AI and analytics deployments across the team — including time savings, faster insight delivery, and reduced manual reporting burden — tracked and reported quarterly
• Field Operations effectiveness: Business review scores, segment NPS for RevOps partnership, and the volume of self-serve analytics and AI tools deployed in the field improve year-over-year
• Team development: Field Operations leaders demonstrate measurable growth in analytics and AI capabilities, with clear evidence of skill progression and retention