Head of Advocacy

The federal government spends over $700 billion a year hiring private companies to do critical work, from staffing veterans' hospitals and maintaining military bases to supporting federal logistics and IT for federal agencies. Many of those contracts legally require employers to set aside money for employee benefits, earned hour by hour. Today most of that is managed through spreadsheets, disconnected vendors, and compliance rules that are nearly impossible to navigate — so employers overspend and risk audits, and workers end up with benefits they can't use or never fully access.

CVRD is the modern tech that fixes it: employers track benefit dollars in real time, stay compliant, and manage healthcare and retirement in one place, while workers finally get benefits they understand.

But technology is only part of the solution. Healthcare is personal. Benefits are personal. Behind every enrollment, eligibility issue, or coverage question is a real person trying to take care of themselves or their family. That's where our AI-enabled Advocacy team comes in.

Our advocates help workers understand their benefits, navigate enrollment, resolve issues with carriers and marketplaces, and make sure they actually receive the benefits they've earned. They're problem-solvers, educators, and trusted guides during moments that can often feel confusing and frustrating.

As we continue to grow, we're looking for a Head of Advocacy to lead that team and define what exceptional member support looks like. This is an opportunity to build a modern, AI-enabled advocacy function and call center in an industry that has traditionally relied on fragmented systems and manual processes.

Much of the team's work is operational and outbound. Advocates work directly with carriers and marketplaces to resolve eligibility issues, push enrollments through, and untangle the countless discrepancies that arise throughout the benefits lifecycle. The rest of the work is member-facing: helping workers understand their options, guiding them through enrollment, and showing up when they need support.

As Head of Advocacy, you'll stay close to this work while building the systems and team that allow it to scale. This is a true player-coach role. You'll help resolve complex cases yourself, coach and develop advocates, manage performance, and create an environment where people can do their best work.

You'll own the processes, standards, and operating rhythms that shape the member experience. You'll partner closely with leadership to identify opportunities for automation, improve workflows, and determine what should be handled by people versus technology. We believe advocates should spend their time solving meaningful problems and supporting members, not pushing paperwork. You'll help build the systems that make that possible.

Success in this role requires equal parts leadership, operational rigor, and customer empathy. We're looking for someone who can develop people, improve processes, and bring structure to complexity without losing sight of the human being on the other side of every interaction.

• Lead and grow a team of 4-5 full-time advocates, scaling up during peak periods as needed. Hire thoughtfully, coach consistently, and help people get visibly better at their customer service craft.
• Own our carrier and marketplace relationships, along with the day-to-day work of getting enrollments processed and issues put to bed.
• Stay close to complex cases, helping resolve escalations, spot patterns, and turn recurring issues into better processes.
• Own the member experience across enrollment, eligibility, carrier issues, marketplace questions, and follow-up support.
• Partner with engineering to bring AI and agentic tools into the workflow — deciding where automation genuinely helps and where a human needs to stay close.
• Build the training, onboarding, QA standards, reporting, and operating rhythms that help the team scale without losing quality.
• Use data to understand team performance, member needs, volume trends, resolution times, and where the function can keep getting better.
• Bring insights from the front lines back to leadership, product, and operations.

• A real love of customer experience, and a clear point of view on what great support should feel like in health insurance.
• Hands-on experience with health insurance and enrollment, including open enrollment, eligibility, life events, carrier workflows, marketplaces, TPAs, and the real-world friction members run into.
• High emotional intelligence and a natural pull toward leading, coaching, and developing a team.
• A deep belief in training, with a track record of people who grew because you taught them.
• Strong operational judgment around when to escalate, when to solve, when to document, and when a process needs to change.
• The ability to bring structure to complicated workflows without making the work feel heavier than it needs to be.
• Genuine curiosity about AI, automation, and agentic tools, with the instinct to build toward where customer support is heading instead of protecting the old way of doing things.
• Comfort staying close to the day-to-day work while also building the standards, systems, and team rhythms that help the function scale.

• You lead from the front. You are not above the work, and you do not need everything to be perfectly built before you start making it better.
• You notice patterns. You see where the team is losing time, where members are getting stuck, and where a process needs to be rebuilt instead of patched.
• You care about people and operations in equal measure. You want the member to feel supported, the advocate to feel prepared, and the system to get sharper every week.
• You are energized by building something new. You like bringing order to complexity, but you do not need a giant playbook handed to you. You are comfortable writing the playbook as you go.

This is a rare chance to define what modern benefits advocacy looks like from the ground up. You will lead a real team, solve real member problems, and help shape the systems that make the work scalable.

You will work closely with the CEO, senior leadership, product, and engineering, which means your perspective will directly influence how the company builds, operates, and supports members. This is not a support role tucked away in a corner. Advocacy is core to the product experience.

If you want to build a function you can point to and say, "I made that better," this is the kind of role where that can actually happen.

We're an early-stage, venture-backed company building the operating system for the people side of government contracting. We move quickly, care deeply about the workers our customers employ, and hold ourselves to a high standard.

We're building something ambitious, and that requires people who are curious, accountable, and excited to solve hard problems. If you enjoy creating order from complexity, improving systems, and helping shape how a company grows, we'd love to hear from you.