Senior Pricing Analyst

Headspace

20d•$99,000 - $138,000•Hybrid

About The Position

The Senior Pricing Analyst will be a key contributor on the Actuarial & Pricing team, working closely with Sales, Finance, and Go-to-Market teams. This role owns deal-level financial modeling and underwriting, competitive pricing intelligence, and the analytical work that connects pricing strategy to commercial outcomes. This role directly influences pricing strategy both on the deal and enterprise level. Reporting to the Director of Actuarial Analytics & Pricing, this position plays a central role in how Headspace prices, positions, and wins in the market. The ideal candidate brings rigor to a fast-moving, non-traditional environment and is comfortable operating across both technical and business-facing workstreams.

Requirements

Bachelor's degree in Finance, Economics, Mathematics, Statistics, Actuarial Science, or a related quantitative field
5+ years as an actuary, pricing analyst, financial analyst, or similar
Extensive financial modeling experience in Excel or Google Sheets
Data analysis skills (proficiency in R, SQL, Python)
Strong interpersonal skills to collaborate, mentor peers, and influence stakeholders
Experience supporting sales or commercial teams in a deal desk, pricing, or strategic finance capacity
Experience working in the healthcare industry.

Nice To Haves

Background in digital health, employee benefits, or value-based care—particularly mental health
Familiarity with SaaS or subscription-based pricing models, including PMPM structures, tiered pricing, and usage-based constructs.
Strong presentation, project management, and problem-solving skills
Experience with end-to-end assumption setting: conducting studies, documenting findings, communicating results
Proven ability to manage competing priorities and communicate analytical findings to non-technical audiences across cross-functional teams

Responsibilities

Own and enhance Headspace's pricing strategy by upgrading assumption pipelines, testing assumptions, and optimizing pricing models with cross-functional teams.
Build competitive pricing intelligence, turning market signals, win/loss data, and industry trends into recommendations for GTM leadership.
Analyze engagement and financial data to connect price points to deal outcomes—win rates, renewals, and deal economics—including churn/renewal drivers.
Translate analyses into clear narratives that equip client-facing teams to drive decisions.
Support deal desk with financial analysis and documentation for pricing approvals.
Partner with Finance to ensure pricing structures are consistent with revenue recognition standards and support audit-readiness.