Head of Strategy & Operations

💡 Mission

The US healthcare system is complex, error-prone, and financially draining. Medical bills and insurance coverage shouldn’t be this hard to navigate. At Granted, we’re building the one solution every American can turn to for help.

Thanks to AI and new regulations, Granted can fight claim denials, correct billing errors, negotiate bills, and make coverage easier to understand—saving people time, money, and stress. Our goal is simple: to be the #1 platform that empowers all Americans to take charge of their healthcare.

🩺 About Us

Founded by a former Oscar Health leader, we’re a seed-stage company with $17M in funding. We’re lucky to be backed by the founders and investors at Hugging Face, Rocket Money, Oscar Health, CaseText, Forerunner Ventures, RRE Ventures, and more. We are well-funded for the next few years.

🚀 About the Role

We’re looking for a Head of Strategy & Operations to help define and drive how Granted grows. This role is equal parts business strategy, go-to-market, and scrappy execution.

We’ve raised $17M to tackle one of the hardest consumer problems in America, and now we’re defining where to focus and how to scale. As Head of Strategy & Ops, you’ll help shape answers to questions like: Which customer segment do we double down on? What distribution channel unlocks growth? How do we turn complex regulation into an advantage?

You’ll work very closely with our CEO and other leaders on top company priorities—bringing structure to ambiguous challenges, running fast-paced experiments, and building the internal infrastructure that will help us scale. You’ll sit at the intersection of product, ops, and leadership, and be trusted to own high-impact projects from end to end.

This is a high-autonomy role for someone who thrives on turning insight into action and cares deeply about fixing the system for consumers.

You speak healthcare. Whether through healthtech, payers, or benefits, you know how the system operates and where it breaks for consumers. That fluency will help you shape strategy and focus the team on the highest-impact opportunities.

💼 What You’ll Own

• Strategic Initiatives & Special Projects
• Partner with the CEO to scope and drive cross-functional projects that are undefined but mission-critical.
• Own and drive cross-functional projects across product, ops, and growth, especially those that are undefined but mission-critical.
• Support fundraising and board strategy with data, modeling, and narrative.
• Market Discovery & User Strategy
• Help identify the most valuable customer segments and problem areas to focus on. Size opportunities, build frameworks, and inform product direction.
• Regulation & Competitive Research
• Track how the healthcare and AI landscapes shift from coverage rules to new market entrants and distill these trends into strategic recommendations.
• Internal Infrastructure & Systems
• Design and implement lightweight systems for internal tracking, analysis, and ops workflows. Make sure the trains run on time as we grow.
• Analytics & Decision Support
• Build models, structure dashboards, and run deep dives to help the team make better decisions faster across product, ops, and user engagement.

🎯 You'll Be a Fit If You...

• Have 10+ years of experience in strategy, consulting, investing, or operating roles, ideally with direct early-stage startup experience.
• Are skilled in business modeling, market sizing, competitive analysis, and zero-to-one problem-solving.
• Know healthcare — whether through a payer, benefits platform, or healthtech startup. You understand the complexities of coverage, claims, and billing.
• Have worked directly with founders or exec teams on strategic decisions.
• Can take a messy, open-ended problem and turn it into an actionable plan.
• Have strong analytical and financial modeling chops.
• Communicate clearly and work seamlessly across functions.
• Thrive in fast-paced, high-ownership environments.

🌟 Bonus If You...

• Have launched or managed GTM bets, P&L lines, or new business models.
• Have an MBA or equivalent experience in managing growth bets.
• Bring a technical foundation (CS, data, math) that helps you bridge product and strategy.
• Care deeply about solving real-world problems for real people.

🦸 Working with Us

Granted is based in New York. Our team is split evenly between our Chelsea office & the US. We marry the best of in-office culture with the best of a remote-first company.

We’re a team of passionate individuals who show up every day to do the best work of their lives following these principles:

• Move with Urgency and Focus: Prioritize what matters and find the shortcuts.
• Own the Outcome: Take initiative and see it through until the end.
• Commit to Your Craft: Excellence is the standard. Care about the details.
• Play to Win: If we win, Americans win, so we work hard and do what it takes for us to be #1.
• Feedback is Fuel: Intellectual honesty is at the core of everything we do.
• We’re One Team: Together, we can achieve things that none of us could on our own.

Granted is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, age, protected veteran status, disability, or any other legally protected characteristics.

We are also committed to providing reasonable accommodations to qualified individuals with disabilities. If you need assistance or an accommodation during the application or interview process, please contact us.