Chief of Staff

Most of what makes American healthcare expensive isn’t medical care. It’s the machinery wrapped around it: middlemen taking a cut, fraud nobody stops, and billing systems designed to fight over payment instead of deliver care. The result is higher premiums, denied claims, surprise bills, and a system patients increasingly experience as adversarial.

Arlo is rebuilding health insurance for small businesses from first principles: making sure as much of every premium dollar as possible goes to care instead of getting absorbed by the system around it. We do that by identifying fraud earlier, steering members toward higher-quality and lower-cost care, automating operational overhead, and eliminating vendors whose business exists mostly to take a cut.

AI is the foundation that makes this work. We use it across underwriting, operations, clinical programs, and member experience to build an insurer that becomes more efficient as the technology improves.

We’re already operating at meaningful scale: profitable, hundreds of millions in premiums, tens of thousands of members covered, and growing quickly through brokers, employers, and partners. Backed by Upfront Ventures, 8VC, and General Catalyst, with a team from Palantir, YC companies, and longtime healthcare operators.

We are building an AI-native health plan and need to build several functions, capabilities and teams over the course of the next few months and years. Your role will be to beachhead these initiatives, bring them from 0 to 1 and set them up for success. You will be working directly with Arlo's founders to act as a thought partner, lead strategic, cross-functional projects and spin up new functions. Here are some example projects you would be leading:

• Design and drive key marketing experiments

• Setup a clinical team

• Architect partnerships with key distribution partners

• Setup an insurance captive company

• Execute on Strategic Projects: Plan and execute key initiatives in close collaboration with Arlo's founders

• Spin up new functions: Design, build and operationalize new functions (prototype & run new processes/ capabilities, define new team roles, manage transition from "prototype into production")

• Recruit, Onboard and Scale new Teams: You will be working closely with Arlo's talent lead to ensure your new functions are properly staffed. onboarded and can thrive moving forward.

• Strategic Support: Support founders with planning, decision making and operational follow-through

• 5+ years of experience in a high-intensity settings (consulting, investment banking, high growth startup, etc.)

• Ability to operate as a generalist and learn extremely fast to dive deep into a topic (T-shaped profile).

• Strong bias for action, sense of ownership, and ability to dive into the weeds.

• Strong analytical and problem-solving skills; comfortable working with metrics and data.

• High emotional intelligence, integrity, and collaborative spirit.

• Evidence of building or scaling functions or teams at an early or fast-growing company.

• Ex-Founders are highly welcome to apply

This is what you can expect when we like your application:

• 30 minute call with Rachelle (Talent Lead)

• 30-minute introductory call with Jan-Felix (CEO & Co-Founder)

• 30-min call with Karthik (Co-Founder)

• Take-home case study

• Onsite/ Virtual Onsite

• Reference Calls

$175,000 – $225,000 per year + equity

• High ownership: You’ll get real responsibility from day one—our high-trust team empowers you to run with big problems and shape core parts of the company.

• Join an important mission: Your work directly influences how people access care and improves lives at scale.

• Growth & expansion: We’re moving fast, and as we grow, your scope will grow with us—new challenges, bigger opportunities, and rapid career velocity.

• Apply AI to a problem that matters: Instead of optimizing ads or cutting labor costs, you’ll use AI to fundamentally reimagine how people get healthcare.

• High pace, high collaboration: We operate with velocity, first-principles thinking, and a team that works closely, openly, and with ambition.

Exact compensation inclusive of salary and any bonuses is determined based on a number of factors including experience and skill level, location, and qualifications which are assessed during the interview process.
Arlo is an equal opportunity employer. We do not discriminate based on age, race, color, creed or religion, national origin, sexual orientation, gender identity or expression, military status, sex, disability, predisposing genetic characteristics, marital status, familial status, status as a victim of domestic violence, or arrest or conviction record, as defined under New York State law.
🔒 Your safety matters to us. If you're selected to move forward in our hiring process, you'll hear directly from a member of our Recruiting team via an @joinarlo.com email address. We will never ask for personal or financial information outside of our formal onboarding process. When in doubt, please reach out to us to verify at: [email protected].