Manager/ Director Sales Enablement & RevOps

ArloNew York, NY
2d$150,000 - $200,000

About The Position

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.

Requirements

  • 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

Nice To Haves

  • 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

Responsibilities

  • 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

Benefits

  • 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.
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