Office of the Founders (backed by Y Combinator, $5M+ ARR, $20M+ raised)

Legion Health•San Francisco, CA

17d•$120,000 - $210,000•Onsite

About The Position

Legion is hiring someone unusually sharp early-career technical operator who will work directly with leadership to solve high-leverage problems across growth, revenue, finance, hiring, culture, legal, investor work, operations, and internal AI systems (Office of the Founders). This is not an executive assistant role. It is not a traditional business operations role. And it is not a junior Chief of Staff role with a better title. It is a new kind of role for the AI-native era: a technical, high-agency generalist embedded with senior leaders to make the company dramatically faster. You will sit close to leadership, see the company’s most important problems early, and be expected to build solutions fast. One day you might prototype an internal AI tool that saves the operations team 30 hours per week. The next day you might analyze patient reactivation, build a GTM model, improve a hiring process, automate investor reporting, draft a strategy memo, or create a workflow that helps a non-technical team specify exactly what they need before engineering gets involved. The center of gravity is GTM and company leverage. You should constantly be asking: where are we losing patients, revenue, speed, quality, or focus, and what can I build, automate, analyze, or fix this week to move the company forward? The best candidates are likely 0-3 years out of school, with a computer science, engineering, data science, operations research, financial engineering, applied math, statistics, economics, or similarly rigorous background. You may have early experience in consulting, banking, finance, startups, product, data, or engineering. What matters most is raw intelligence, speed, taste, grit, communication, AI fluency, and demonstrated ability to make things. This is a career-accelerating role for someone who wants unusual exposure very early. You will be in the room for meaningful company decisions, work directly with senior leaders, get tough deadlines, and learn by doing real work that matters.

Requirements

0-3 years of experience in a high-performance environment such as consulting, investment banking, private equity, strategic finance, startup operations, product, data, engineering, or a similarly intense setting.
Strong preference for a technical or quantitative degree: computer science, engineering, data science, operations research, financial engineering, applied math, statistics, economics, or similar.
Demonstrated competency in making things and automating things. You have built projects, scripts, tools, automations, prototypes, dashboards, agents, websites, apps, analyses, or workflows that actually worked.
Deep AI-native working style. You do not just “use ChatGPT.” You use AI tools to build, analyze, automate, prototype, research, write, debug, synthesize, and move faster every day.
Ability to build lightweight tools or prototypes using some mix of Python, JavaScript, SQL, spreadsheets, APIs, no-code tools, AI coding tools, product prototyping tools, and data platforms.
Strong analytical horsepower. You can build a model, interrogate assumptions, analyze a funnel, understand unit economics, and explain what matters.
Strong GTM instincts. You care about patient growth, revenue, conversion, retention, activation, reactivation, CAC, payback, funnel dropoff, and the practical mechanics of moving numbers.
Excellent written communication. You can write a memo, investor update, recruiting note, project spec, growth analysis, operating plan, or executive summary that is crisp and useful.
Strong people judgment. You can work with founders, operators, clinicians, engineers, lawyers, candidates, investors, and vendors without losing context or trust.
Comfort with sensitive information. You can handle patient, company, legal, financial, recruiting, investor, and operational information with maturity and discretion.
High agency and low need for structure. You do not wait for someone to define the perfect project. You find leverage and go create it.
High-conviction interest in Legion. This role is intense, ambiguous, and close to leadership. It is best for someone who genuinely wants to be here and sees this as a chance to put their career on a much faster track.

Nice To Haves

You want a narrow lane with a fixed job description.
You prefer advising over doing.
You cannot figure what to do to move the needle and operate without much direction.
You are not deeply curious about AI tools.
You need engineers or analysts to answer every first-pass technical or data question.
You are uncomfortable with growth, revenue, or commercial pressure.
You optimize for looking strategic instead of creating measurable leverage.
You want prestige without intensity.
You do not want to work closely with leadership in a high-speed environment.
You are not excited to work in person, close to the team, with real urgency.

Responsibilities

Work directly with founders and leadership on high-priority projects across GTM, growth, revenue, business operations, regulatory, finance, hiring, culture, legal, investor relations, product, and internal systems.
Drive go-to-market and revenue projects across new patient acquisition, conversion, retention, reactivation, referrals, lifecycle, pricing, patient experience, and funnel optimization.
Build AI-native tools, workflows, dashboards, scripts, agents, prototypes, and automations that help teams operate faster and better.
Rapidly prototype solutions for non-technical teams so they can clarify what they want before full engineering resources are used.
Identify bottlenecks across the company, diagnose root causes, and build fast solutions: models, dashboards, workflows, memos, trackers, experiments, or internal products.
Use AI coding and building tools like Codex, Claude Code, Cursor, Replit, v0, Lovable, ChatGPT, Claude, Perplexity, APIs, scripts, and no-code tools to move faster than a normal early-career operator.
Build internal systems for leadership: synthetic advisory boards, investor update workflows, meeting-prep agents, board-material review systems, recruiting trackers, finance dashboards, GTM dashboards, and executive decision-support tools.
Support strategic finance work: revenue models, CAC/payback analysis, hiring plans, budget scenarios, growth forecasts, investor updates, board materials, and operating reviews.
Help build Legion’s talent machine: sourcing systems, role scorecards, interview loops, candidate evaluation processes, onboarding systems, culture rituals, and performance operating rhythms.
Partner with growth, product, data, clinical operations, and leadership to analyze the patient journey: intake, booking, first visit, follow-up, renewals, retention, churn, and reactivation.
Support legal, compliance, regulatory and finance workflows with maturity and attention to detail, especially around healthcare, HIPAA, contracts, vendors, employment, patient communication, and AI sandboxes.
Write crisp memos, project plans, launch docs, investor materials, candidate materials, process docs, and internal updates that create clarity quickly.