Employee BENEFITS IMPLEMENTATION LEAD

Benefits Implementation Lead

Employee Benefits

• Operations × Product
• Founding Team Hire
  
  

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

The Short Version

Think of this as a more junior, more technical version of an Account Manager profile.

You should have 3-5 years of experience in benefits account management or implementation, but 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, Yuri, will work closely with you as part of this process.

You are the subject-matter expert our AI tools learn from.

Two Hard 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 genuinely technical.

You should 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.

Our Favorite Screening Question Is

"Show me something you built or automated."

If you cannot show us something you have built or automated, pass.

Why This Role Exists

We are the AI-native employee benefits brokerage for companies with 25-200 employees. We believe the $900B employer benefits market is broken: opaque, manual, and stuck in the 1990s. We are changing that with technology, transparency, and a radically better client experience. Our pitch to clients is simple: 15 minutes can save you $100,000 per 25 employees.

This role sits at the exact intersection of where we are going. Half of your job is running benefits implementations for real clients: broker-of-record transitions, carrier setup, plan builds, enrollment platform configuration, and renewals. The other half is turning that work into software, partnering directly with our engineering team to design, test, and ship the AI agents and internal tools that automate the workflows you just ran by hand.

You will work alongside a Head of Account Management with 15 years of experience servicing a mid-market block, learning the craft from one of the best in the business, while building the systems that mean we never have to do it the old way again.

You are not inheriting a playbook. You are writing it, and then you are shipping it as product.

What You'll Own: 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.
  
  

What You'll Own: 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.
  
  

Who You Are

• 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
• Genuinely technical: You are a power user of spreadsheets and AI tools, comfortable with structured data, and curious about how software gets built. You have probably already automated part of your own job.
• 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.
• Based in the Bay Area or willing to relocate to Mountain View, CA. This role is in person.
  
  

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)

Metric

Target

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