Senior Manager, Client Success

CVRD Health (pronounced “Covered”) was built to fix a very real problem in a very complicated space.

Government contractors are stuck dealing with rising benefit costs, fragmented systems, and growing compliance pressure, all while trying to run their actual businesses. CVRD created tech that exists to turn that chaos into something predictable, compliant, and human. That means less administrative burden, better visibility, and making sure every benefit dollar is doing what it’s actually supposed to do.

With streamlined CHOICE administration, real-time insights, and a platform designed specifically for GovCon compliance, CVRD helps employers focus on running their business, not fighting their benefits. We’re not just optimizing fringe benefits. We’re raising the bar for what contractors should expect from their benefit partners.

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We’re looking for a Senior Manager, Client Success to help own the day-to-day of our client relationships — the work that makes CHOICE and prevailing wage administration actually run.

This is a hands-on role. You’ll be the person our clients’ HR, payroll, and finance teams talk to regularly: eligibility and enrollment, invoicing and reconciliation, carrier issues, plan year changes, and the hundred small things that have to be right for benefits to feel effortless. You’ll also be the connective tissue between our client teams, our member advocates, and product.

We need someone who has actually done benefits administration — not someone who has only managed people who do it. If you’ve run an eligibility file, chased a carrier on a termination that never took, reconciled an enrollment that didn’t match the census, and explained a plan change to an HR manager in plain English, you’ll recognize this job.

You’ll report to our Director of Client Success and be the operational other half of that partnership: they own the plan and overall client strategy; you own the day-to-day execution and client relationship. New clients are coming onboard now and Open Enrollment is the loudest stretch of our year, so this seat matters immediately — we need someone who can stand up a new group cleanly while keeping the existing book steady.

As Senior Manager, Client Success, you’ll be responsible for:

• Owning the day-to-day relationship with an assigned book of employer clients — the weekly rhythm, not just the quarterly check-in
• Onboarding and implementing new clients: census and data collection, plan and platform setup, payroll and carrier connections, employee communications, and a clean first payroll and first invoice
• Partnering with the Director of Client Success on client readiness — turning the plan for each new or renewing account into an executed onboarding, on schedule
• Running benefits administration end to end: eligibility, enrollment, qualifying life events, terminations, and data accuracy across payroll, carrier, and platform systems
• Managing premium billing, invoicing, and reconciliation — and catching discrepancies before your clients do
• Owning carrier and vendor escalations through to resolution
• Executing Open Enrollment for your book: timelines, plan setup, client and employee communications, and post-OE cleanup
• Supporting CHOICE administration and prevailing wage fringe reporting so every benefit dollar is documented, defensible, and compliant
• Partnering with our advocacy team so member issues and client issues never fall between the two
• Building and maintaining SOPs, client documentation, and account records so the work is repeatable and doesn’t live in your head
• Setting the bar for how client work gets done — coaching teammates on the details and being the person others check their work against
• Surfacing patterns to Product and Engineering: what’s manual, what’s breaking, what should be automated
• Supporting renewals and expansion by keeping clients healthy, informed, and unsurprised

This is a hands-on role. You’ll be doing the work and improving how it gets done at the same time.

What success looks like

In your first 90 days:

• You’ve taken over the day-to-day on your accounts, and our HR and payroll contacts know exactly who to call
• New clients are onboarded on schedule, with accurate data, a clean first payroll, and a correct first invoice
• The onboarding steps live in a checklist and a set of SOPs — not in someone’s head
• You and the Director of Client Success have a working rhythm: they plan it, you align on the plan and own execution, nothing falls between the two of you
• You’re ready for Open Enrollment — plan setup, timelines, and client communications mapped well before October 15

Within your first year:

• Your clients renew — on time, without drama
• Your HR and payroll contacts hear about issues from you first, not the other way around
• Open Enrollment runs clean for your book, with problems caught in prep instead of in December
• Eligibility, enrollment, and billing data reconcile month over month — and you can prove it
• The process you run is documented well enough that the next hire can learn it from the docs
• Recurring manual headaches have been automated away or eliminated, not just absorbed - your product colleagues are better because of your efforts
• Clients see you as a trusted partner who knows their business, not a support contact

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You’re a benefits administration operator who likes clients and details in equal measure.

You likely:

• Have 5+ years in benefits administration — at a ben admin platform, brokerage or consulting operations team, TPA, carrier, or in-house benefits function
• Know eligibility, enrollment, life events, COBRA, Section 125, ACA reporting, and carrier file and EDI processes cold
• Have run new client onboarding from signed contract to first live payroll deadline, building the plan set-up, eligibility rules, and carrier feeds without hand-holding
• Have worked hands-on in a ben admin or HRIS/payroll system (Employee Navigator, bswift, PlanSource, Ease, ADP, Paylocity, UKG, or similar) and can pick up a new one fast
• Have owned client relationships directly with HR managers, payroll leads, and finance — including the hard conversations
• Are relentlessly organized, follow through without being chased, and catch the thing everyone else missed
• Can explain complex benefits mechanics in a clear, human way
• Are comfortable with ambiguity and building process where none exists yet
• Bonus points for CHOICE or HRA administration, GovCon fringe benefit administration experience, or familiarity with SCA / Davis-Bacon prevailing wage and fringe regulations

You don’t need to know everything about GovCon or CHOICE on day one — we’ll teach you that. You do need to know benefits administration on day one, because that’s the core of the job.

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• Hybrid role with occasional travel for client meetings and conferences
• New client onboardings and Open Enrollment drive the calendar — the work is deadline-driven and comes in waves
• Open Enrollment (October 15 – December 31) is our busy season and our loudest stretch of the year — there is a company-wide vacation blackout during that window
• Flexibility to shape your approach and schedule around your client commitments
• Close collaboration with leadership, advocacy, product, and operations

Why CVRD

• You’ll operate like an owner. No micromanagement, minimal red tape. If something needs fixing or building, you’re trusted to own it and move.
• You’ll work closely with our Director of Client Success and the broader leadership team, with real authority over how the work gets done in your accounts.
• We don’t expect you to know everything on day one. We do expect good judgment, curiosity, and a willingness to learn. We’ll give you the tools and support to do that.
• If you need resources, support, or eventually a team to do the job well, we’re aligned on making that happen.
• We care about outcomes, not hours or where you work. Work how you work best, as long as the work is done well.
• You’ll be part of a sharp, entrepreneurial team that takes pride in doing things right and getting things done.
• We move fast, support each other, and don’t add process unless it actually helps.

CVRD Health is an equal opportunity employer. We’re committed to building a diverse, thoughtful, and inclusive team.