EnrollHere is on a mission to make healthcare enrollment simple, transparent, and accessible for everyone. We partner with organizations nationwide to deliver streamlined technology and exceptional customer experiences, ensuring members can access the coverage they need with confidence. Our fully remote team thrives on collaboration, innovation, and a shared commitment to improving the enrollment journey for all.

As an Account Executive within the Customer Success Team, you’ll own post-sale growth and relationship management for a portfolio of carrier and distributor clients. You’ll act as the bridge between our clients’ business goals and our technology solutions—helping them realize measurable value, expand adoption, and drive renewals. This is a hybrid role blending strategic account management, consultative selling, and client success - perfect for someone who thrives at the intersection of relationships, data, and results.

Serve as the primary commercial point of contact for assigned accounts, ensuring client satisfaction, retention, and growth. manage renewals and negotiate contracts with support from leadership. Partner with Customer Success Managers, Product, and Solutions teams to align platform capabilities with evolving client needs.

Strategic account planning: Develop account plans to forecast growth, mitigate churn risk, and build multi-level stakeholder relationships (business, IT, operations).

Performance insights: Voice of the customer:



Capture client feedback and advocate internally to shape roadmap priorities and improve user experience. Stay informed on regulatory trends (CMS, ACA, Medicare Advantage, life licensing, compliance) to serve as a trusted advisor to clients. 3+ years of experience in SaaS account management, renewals, or customer success (preferably in B2B enterprise software). Understanding of the health and life insurance industry, including carriers, distributors, FMOs, and agency operations.

Proven success managing renewals and expansion quotas with a consultative, data-driven approach. Strong organizational and CRM proficiency (HubSpot, Salesforce, or similar). Willingness to travel ~50% of the time Experience working with compliance, licensing, or data exchange software in the insurance ecosystem.

Familiarity with health plan operations, broker distribution, or Medicare Advantage processes. 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) 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) Generous PTO and work from home support Learning stipents and opportunities for professional development #

📌 Account Executive, Customer Success (Winnipeg)
🏢 EnrollHere
📍 Winnipeg