• Lead high-impact strategic initiatives across Underdog’s core business lines – including prediction markets and fantasy sports – translating ambiguous problems into clear recommendations for senior leadership • Build and maintain financial models supporting high-stakes strategic and commercial decisions, including complex multi-party transactions and partnership structures • Conduct rigorous analysis of market trends, competitor positioning, and customer behavior to surface actionable insights and inform long-range planning • Own the development of strategic roadmaps, defining short- and long-term objectives and metrics to track progress against them • Serve as a connective tissue between business units, synthesizing cross-functional inputs and ensuring alignment across product, finance, marketing, and operations • Prepare board-level and executive-facing materials that distill complex analysis and trends into clear narratives • Identify and evaluate new business opportunities, partnerships, and adjacencies that align with Underdog’s growth strategy

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About The Role As Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients. As a Business Operations Lead, you will drive complex, cross-functional initiatives that advance pod-level objectives. You'll work independently to identify opportunities, address dependencies, and ensure alignment across stakeholders - turning ambiguous problems into structured analyses, scalable processes, and clear recommendations. You'll bring analytical rigor to root-cause investigations, design workflows and tooling that improve efficiency and reliability, and own initiatives end-to-end from scoping through delivery. This role requires strong problem-solving skills, a builder's mindset toward operational design, and the ability to coordinate across teams to drive measurable outcomes. What you’ll do at Headway - Drive complex, cross-functional initiatives that advance pod-level objectives - identifying opportunities, addressing dependencies, and ensuring alignment across stakeholders. - Build and operate scalable workflows and processes (0→1) that improve efficiency, reliability, and throughput across your domain. - Leverage data tools to extract insights, validate assumptions, and inform decisions, synthesizing findings into clear recommendations that guide pod and organizational priorities. - Plan, execute, and deliver initiatives end-to-end by setting clear objectives, timelines, and success metrics – driving accountability across functions without formal authority. You’ll be great for this role if you: - You have 5+ years of experience in operational roles at high-growth companies; background in consulting, finance, or business operations preferred but not required. - You independently deconstruct complex problems into structured, testable components - and you're comfortable working through ambiguity without waiting for full clarity. - You're proficient with AI & data tools (e.g., Looker, Excel, SQL, dashboards) and use them fluently to extract insights, validate assumptions, and streamline workflows. - You design systems with scale in mind - anticipating bottlenecks, iterating based on feedback, and codifying learnings into playbooks and standards. - You coordinate resources and align priorities across teams, building trust through transparency, accountability, and clear communication. - You take calculated risks and make decisions that advance pod objectives, anticipating downstream impacts before taking action. - You're motivated by the opportunity to make an impact on one of our generation's defining problems: affordable mental healthcare. Compensation and Benefits: The expected base pay range for this position is $105,400 - $155,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. - Benefits offered include: - Equity compensation - Medical, Dental, and Vision coverage - HSA / FSA - 401K - Work-from-Home Stipend - Therapy Reimbursement - 16-week parental leave for eligible employees - Carrot Fertility annual reimbursement and membership - 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st - Flexible PTO - Employee Assistance Program (EAP) - Training and professional development We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

• Lead complex, cross-functional special projects from concept to execution (e.g., evaluating new market entry strategies, optimizing customer onboarding pipelines, or structuring commercial pricing frameworks). • Build the quantitative models, dashboards, and frameworks necessary to track company-wide KPIs and evaluate new business opportunities. • Serve as the connective tissue between technical AI/ML engineering teams, product managers, and commercial leads to drive alignment on high-priority company objectives. • Audit existing startup processes, identify bottlenecks, and design highly efficient, scalable workflows that allow our operations to keep pace with our technical scaling. • Synthesize intricate technical and financial data into polished, high-impact narratives and presentations for leadership and board-level discussions.

• For the first few months, you will join an existing product team, and learn how we think about and develop products. • Learn how to conduct customer research, write product specs, work with engineers and designers, use tools like Figma and Codex to prototype, design and run experiments, analyze outcomes, and incorporate learnings into iterative product decisions. • Take one of our target verticals from concept to a revenue-generating product. Run the incubation, build and ship the product, test and iterate, and then hire a team to run it.