Sr. Director, Pricing

What you’ll do Lead Enterprise Pricing Strategy & Governance

• Lead a central deal desk function that enables consistent, disciplined pricing decisions.
• Define and evolve enterprise pricing frameworks that balance profitability, competitiveness, and customer value across ASO, value-based care, and SaaS-like pricing constructs.
• Own pricing governance, including approval flows, pricing guardrails, documentation, and ongoing auditability.

Drive Strategic Deal Structuring & Execution

• Support sales teams on complex or non-standard deal pricing — creating flexible yet disciplined approaches that protect unit economics and accelerate close rates.
• Develop margin-centric playbooks, concession matrices, and pricing decision tools for quota-carrying field teams.

Modeling, Insights & KPI Strategy

• Partner with Strategic Finance to build robust pricing models (PMPM, bundles, usage-based, value-based, outcome-linked pricing).
• Define pricing KPIs and dashboards to monitor function productivity and inform leadership decisions.
• Lead scenario analysis (“what-if” modeling) for strategic initiatives, new offerings, and market expansions.

Cross-Functional Enablement

• Collaborate with Product, Clinical/Actuarial, Legal, FP&A, and Rev Ops on pricing approaches for product launches, renewals, and contractual innovations.
• Align pricing strategy tightly with corporate financial goals and unite economic targets.

Team Leadership & Capability Building

• Mentor and scale a high-performing pricing team.
• Promote pricing discipline and analytic rigor throughout the organization.
• Improve pricing tools and tech stack to automate insights and self-serve analytics.

What we’re looking for

• 12+ years of progressive experience in pricing strategy, strategic finance, revenue strategy, deal desk leadership, or related roles — ideally in high-growth SaaS, healthcare technology, or B2B enterprise environments.
• Proven leadership in developing and executing pricing strategies that support both growth and profitability.
• Demonstrated leadership of pricing governance, frameworks, and operational rigor at scale.
• Strong analytical foundation with the ability to build pricing models and articulate tradeoffs between margin, competitiveness, and value.
• Strong analytical and modeling skills, with the ability to evaluate tradeoffs across margin, competitiveness, and customer value.
• Comfort with financial modeling, pricing analytics tools, CRM/CPQ platforms, and advanced Excel.
• Experience working cross-functionally between various stakeholders and influencing senior executives’ decisions through clear, data-driven insights.
• Ability to partner with senior leaders across Finance, Sales, Product, and Legal to align on strategy and decisions.
• Excellent communicator and storyteller — able to translate complex analysis into clear recommendations.
• Bachelor’s degree in Finance, Economics, Business, or a related field is required.
• MBA or advanced degree strongly preferred.

Nice to have

• Background in healthcare or digital health pricing, including employer-sponsored pricing, value-based care, or clinical cost modeling.
• Experience serving enterprise sales teams with complex negotiations and contract arrangements.
• Familiarity with integrating pricing strategy with actuarial and clinical data to reflect cost and value outcomes.

As a remote position, the salary range for this role is: $175,000 — $225,000 USD

Who we are

Transcarent and Accolade have come together to create the One Place for Health and Care, the leading personalized health and care experience that delivers unmatched choice, quality, and outcomes. Transcarent’s AI-powered Way Finding, comprehensive Care Experiences – Cancer Care, Surgery Care, Weight – and Pharmacy Benefits offerings combined with Accolade’s health advocacy, expert medical opinion, and primary care, allows us to meet people wherever they are on their health and care journey.

Together, more than 20 million people have access to the combined company’s offerings. Employers, health plans, and leading point solutions rely on us to provide trusted information, increase access, and deliver care.

We are looking for teammates to join us in building our company, culture, and…