About EnrollHere

EnrollHere is an AI-powered system of record for insurance distribution, purpose-built for the Medicare Advantage ecosystem. We unify marketing, call center infrastructure, agent activity, compliance oversight, policy lifecycle, and commissions into a single platform designed to drive growth, transparency, and operational control.

We believe compliance should be proactive, measurable, and embedded directly into the sales process, not reactive and manual.

The Role

We're hiring a VP of Compliance & Sales Integrity to build and scale a modern compliance organization at the intersection of operations, risk, and technology. You'll report directly to the Chief Innovation Officer. At EnrollHere, compliance is embedded within the technology organization by design, reflecting our belief that compliance and product must evolve together.

You'll serve as both a strategic partner to leadership and a hands-on operator who understands how compliance actually works in the field.

This is a builder role. You won't inherit a rigid structure. You'll create it. Initially hands-on, you'll build a dedicated compliance team as the organization scales.

What You'll Own

1. Sales Integrity, Risk & Investigations Build and lead EnrollHere's compliance and sales integrity function. Design auditing, monitoring, and QA frameworks tied to agent behavior and call activity. Oversee fraud, waste, and abuse (FWA) detection, investigation workflows, and incident escalation. Establish clear standards across agencies, partners, and internal teams.

2. AI-Driven Compliance Systems Partner with product and engineering to embed compliance directly into EnrollHere's platform. Help define and refine AI call-scoring, monitoring, and alerting models, ensuring they align with CMS rules and real-world enforcement expectations.

3. Regulatory Alignment & Operational Enablement Ensure compliance with CMS, state DOI requirements, and carrier expectations. Support audits, reporting, and external reviews. Build SOPs, governance frameworks, and coaching programs that tie compliance outcomes to sales performance so compliance supports growth, not slows it.

Required

• 12+ years in healthcare or insurance compliance
• Deep experience in Medicare Advantage or Medicaid sales compliance, sales integrity, or QA
• Track record of building or scaling compliance programs tied to agent behavior
• Background at a carrier (e.g., Humana, UHC, Aetna) or a large FMO/distribution organization
• Comfort working cross-functionally with product, engineering, and executive leadership

Preferred

• Direct experience leading FWA investigations and incident management programs
• Strong operational background in claims, enrollment, call center, or QA operations
• Familiarity with AI/ML-driven compliance tooling or automation

What Makes This Role Different

• Builder + Operator Hybrid - You'll design the compliance org from the ground up.
• AI-First Compliance - Your expertise will define how compliance is automated and scaled through technology.
• Direct Impact on Product - Your domain knowledge will shape core platform features used across the industry.

We believe in taking care of our team, which is why we offer a comprehensive benefits package that supports your health, wellness, and future:

• Medical: 4 United Healthcare medical plans (including an HSA option)
• Dental: 3 dental plans (Aetna and MetLife)
• Vision: 2 Aetna vision plans
• Wellness & Mental Health: 5 additional Medical Plus benefits, including telehealth support and an annual Talkspace subscription
• Ancillary Coverage: 4 ancillary plans and supplemental life insurance
• Retirement: 401(k) with a 4% match (after a 90-day exclusionary period)
• PTO & Flexibility: Generous PTO and remote work support
• Growth: Learning stipends and opportunities for professional development