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.
Our sales team is expanding, and we need someone to make sure every rep we add ramps quickly, sells confidently, and operates efficiently. This is not a quota-carrying role. It's a force-multiplier role — you'll own the systems, content, training, and analytics that make our sales motion faster, sharper, and more repeatable.
Sales Enablement
Build and maintain our sales playbook — call/ meeting/ demo scripts scripts, objection handling, broker & proposal-specific talk tracks
Own onboarding process for new sales hires, getting them to full productivity as fast as possible
Run ongoing training programs, including incorporating AI-based coaching tools for reps
Create and maintain sales collateral — pitch decks, one-pagers, broker-facing materials, case studies
Listen to calls regularly and translate patterns into coaching and content
Revenue Operations
Own our CRM (HubSpot) — data quality, pipeline structure, workflow automation, rep hygiene
Build and maintain the dashboards that give leadership real visibility into pipeline health, rep performance, and funnel conversion
Identify where deals are stalling and work with sales leadership to address it
Bring structure and repeatability to a sales motion that today lives largely in people's heads
Experience as one of the first Sales Ops or Sales Enablement hires at a B2B company with roughly 20–100 employees
Proven ability to build sales operations and enablement systems from scratch, rather than just maintain existing processes
Hands-on mindset with willingness to personally create materials, configure workflows, and lead trainings
Strong judgment on what good sales process and infrastructure look like, with a practical, low-ego approach
Ability to write sales scripts, build HubSpot workflows, and execute rep training independently
Strong cross-functional communication and comfort working closely with sales leadership
Analytical skills to build and interpret funnel dashboards, pipeline reporting, and sales performance metrics
Bonus Points
Prior quota-carrying sales experience, or enough direct field exposure to have strong credibility with reps
Experience in health insurance, employee benefits, or insurtech is a strong plus
$150,000-200,000 base compensation + annual bonus + 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.