Employee BENEFITS IMPLEMENTATION LEAD

Location: Mountain View, CA (in person)

Department: Client Services & Product

Reports To: Head of Account Management, with a direct line to Engineering leadership

Experience: 3-5 years in employee benefits account management or brokerage operations

Compensation: Competitive base + equity + performance bonus

About the Role

Think of this as a more junior, more technical version of an Account Manager profile. The role is deliberately split 50/50 between benefits operations and product. Half of your time is running real client implementations: BOR transitions, carrier setup, plan builds, renewals, and the operational work required to deliver an excellent client experience. The other half is working directly with our engineering team to turn those workflows into software. You will help design, test, and ship the AI agents and internal tools that automate the work you just ran manually. Our CTO will work closely with you as part of this process. You are the subject-matter expert our AI tools learn from.

Requirements

• In person in Mountain View, CA. This role is in person and embedded with our engineering team. We are looking for Bay Area candidates or people willing to relocate to the Mountain View area.
• Genuinely technical. You do not need to be an engineer, but you must be a power user of spreadsheets and AI tools, comfortable working with structured data, and ideally someone who has already automated part of your own job.
• 3-5 years of experience in employee benefits account management, implementation, or brokerage operations, ideally at a tech-forward shop.
• Deep familiarity with fully insured and level-funded health plans, ancillary benefits, and the carrier/TPA ecosystem.
• Hands-on experience with enrollments, terminations, QLEs, renewal marketing, and benefits administration platforms; Employee Navigator experience is a strong plus.
• Excellent attention to detail and organizational skills: nothing falls through the cracks on your watch.
• Strong written and verbal communication: you can explain a plan design to a CFO and write a spec an engineer can build from.
• California Life & Health license, or willingness to obtain within 90 days of hire.
• An entrepreneurial mindset: you thrive in ambiguity, move fast, and take ownership. You want to build the playbook, not follow someone else's.

Responsibilities

Benefits Operations (50%)

• Client implementations: Own new-client onboarding end to end: BOR letters, carrier connections, plan and rate builds, census and data migration, and enrollment platform configuration. Make liftouts feel effortless for the client.
• Renewal execution: Request and track carrier quotes, build renewal comparisons across fully insured and level-funded options, and support producers through the full renewal cycle.
• Day-to-day servicing: Handle enrollments, terminations, QLE changes, claims escalations, and coverage questions across carrier portals with zero balls dropped.
• Compliance support: Manage the compliance calendar, including ACA notices, Medicare Part D, and COBRA notices, in coordination with carriers and TPAs.
• Carrier & vendor relationships: Build strong working relationships with carrier reps, TPAs, and vendor partners. Be the person they want to pick up the phone for.

Product (50%)

• Workflow-to-software translation: Document every implementation and servicing workflow you run, then work with engineering to spec the automation. You are the subject-matter expert our AI agents learn from.
• Dogfooding & QA: Be the first and toughest user of our internal console, employer portal, and employee-facing AI tools. File sharp bug reports, pressure-test agent outputs against real carrier data, and refuse to ship anything you would not trust with a client.
• Agent training & evaluation: Build the test cases, edge cases, and evaluation criteria that make our benefits AI actually correct: plan rules, carrier quirks, compliance traps, and all the tribal knowledge that never makes it into documentation.
• Data & tooling: Get hands-on with the plumbing: census file formats, EDI and carrier feeds, spreadsheet automation, and AI tools like Claude. You do not need to write production code, but you should be dangerous with data and unafraid of an API doc.
• Product feedback loop: Sit in sprint reviews, shape the roadmap with real client evidence, and make sure what we build matches how benefits actually work in the wild.

Why Join

• A role that does not exist anywhere else: Most benefits people never touch product. Most product people never touch benefits. You will do both, and the career optionality that creates is enormous.
• Learn from the best: You will be mentored by a Head of Account Management with 15+ years managing a mid-market block, and embedded with an engineering team led by a leader who scaled a startup engineering org from 2 to 50+.
• Equity upside: Meaningful equity in a venture-backed company at the earliest stage, backed by top-tier investors who believe in this market.
• Proven founders: Our CEO previously built and sold Plated for $300M, the largest exit in Shark Tank history. You are joining a team that knows how to build and scale.
• AI-native from day one: Every manual workflow you run is a candidate for automation. The grunt work has an expiration date, and you set it.
• Career trajectory: This role grows into implementation leadership, product ownership, or both. You are not filling a seat. You are building two departments at once.

What Success Looks Like (First 12 Months)

• Client implementations owned end to end: 25-40 groups
• Implementation cycle time: Cut by 50% through automation you helped ship
• Workflows converted to product: 5+ core workflows spec'd, shipped, and adopted
• Renewal support: Full renewal cycle support across the book
• Agent accuracy: Evaluation suites in place for every client-facing AI workflow