Manager/ Director Sales Enablement & RevOps

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.

• 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

• 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

• Manage and improve our outbound tooling, sequencing, and lead routing

• 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

• 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