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.Responsibilities

Own client relationships: Serve as the primary commercial point of contact forassigned accounts, ensuring client satisfaction, retention, and growth.Drive expansion: Identify upsell and cross-sell opportunities across our product suite;

Manage renewals and negotiate contracts with support from leadership.Collaborate cross-functionally: 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 churnrisk, and build multi-level stakeholder relationships (business, IT, operations).Performance insights: Monitor platform adoption, usage analytics, and ROI metrics toproactively guide clients toward greater impact and renewal readiness.Voice of the customer:



Capture client feedback and advocate internally to shaperoadmap priorities and improve user experience.Industry engagement: Stay informed on regulatory trends (CMS, ACA, MedicareAdvantage, 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.Excellent communication, negotiation, and presentation skills with C-level andoperational stakeholders.Strong organizational and CRM proficiency (HubSpot, Salesforce, or similar).Willingness to travel ~50% of the timePreferred :Experience working with compliance, licensing, or data exchange software in theinsurance ecosystem.Familiarity with health plan operations, broker distribution, or Medicare Advantageprocesses.Comfort operating in a startup or high-growth environment—self-starter mindset andadaptability required.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 plansWellness & Mental Health: 5 additional Medical Plus advantages, including telehealth support and an annual Talkspace subscriptionAncillary Coverage: 4 ancillary plans and supplemental life insuranceRetirement: 401(k) with a 4% match (after a 90-day exclusionary period)PTO & Flexibility: Generous PTO and remote work supportGrowth: Learning stipends and opportunities for professional development

📌 Strategic Cs Account Exec - Remote, Renewal Growth (Winnipeg)
🏢 EnrollHere
📍 Winnipeg