Braun Board

Account Executive, Customer Success

EnrollHere · Raleigh, NC

Base
Not disclosed
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
2mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon EnrollHere's careers page

The job

What you'd do
You manage post-sale renewals and upsell/cross-sell for an assigned book of health and life insurance carrier and distributor clients, selling EnrollHere's enrollment technology. About 50% travel.
Who you'd sell to
Still reading the posting. Check back within the hour.
Where deals come from
Mostly handed to you: inbound leads or a set list of customers.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay
No pay listed at all.
Transparency
Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market
Open 82 days. Ask why it's been hard to fill.
Company hiring
2 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Green lights

  • SDR or inbound support. You won't be building all of your own pipeline from zero.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

  1. 1.

    What percentage of fully ramped reps hit quota last year?

    OTE is what you could earn. This is how likely you are to earn it.

  2. 2.

    What percentage of reps on the team have been here more than 18 months?

    Tenure shows whether people stay long enough to get paid.

  3. 3.

    Has the comp plan changed in the last 12 to 18 months? What changed?

    A plan that changes every year means the goalposts keep moving.

  4. 4.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  5. 5.

    What are the base and the OTE for this role?

    No point investing hours before you know the number.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

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Full posting
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 for assigned 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 churn risk, and build multi-level stakeholder relationships (business, IT, operations). - Performance insights: Monitor platform adoption, usage analytics, and ROI metrics to proactively guide clients toward greater impact and renewal readiness. - Voice of the customer: Capture client feedback and advocate internally to shape roadmap priorities and improve user experience. - Industry engagement: Stay informed on regulatory trends (CMS, ACA, Medicare Advantage, life licensing, compliance) to serve as a trusted advisor to clients. Requirements - 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 and operational stakeholders. - Strong organizational and CRM proficiency (HubSpot, Salesforce, or similar). - Willingness to travel ~50% of the time Preferred: - Experience working with compliance, licensing, or data exchange software in the insurance ecosystem. - Familiarity with health plan operations, broker distribution, or Medicare Advantage processes. - Comfort operating in a startup or high-growth environment—self-starter mindset and adaptability required. Benefits 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
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