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Mid-Market Account Executive

Seeking a Mid-Market Account Executive. Most conversations will start with Total Rewards or Benefits professionals, then expand to HR, Finance, and executive leadership as the decision moves forward.

This is a full-cycle role. You will develop your territory, lead discovery, deliver tailored presentations, build the business case, and guide each opportunity through procurement and contract signature. Marketing, events, and inbound interest will create additional openings, but building your own pipeline is a core part of the role.

The direct motion is still taking shape, which gives this person a meaningful role in refining how they sell. They are looking for someone who knows the employee-benefits market, is comfortable working with brokers/consultants, understands how employers make buying decisions, and is comfortable creating momentum before every part of the playbook is finished.

What you will own

• Own the Northeast territory, focusing primarily on employers with 500 to 5,000 employees, and build a clear strategy for winning the highest-potential accounts.
• Build your own pipeline through cold calling, email, LinkedIn, and targeted use of outbound prospecting tools, supplemented by marketing, events, website inquiries, and broker introductions.
• Lead the full sales cycle, from discovery and tailored presentations through business case development, procurement, negotiation, and contract signature.
• Build consensus across Total Rewards, Benefits, HR, Finance, and executive stakeholders while positioning the company around each employer's priorities.
• Deliver against new-business goals while maintaining an accurate pipeline and forecast in HubSpot.
• Coordinate a clean transition to implementation and share buyer feedback that helps improve positioning, materials, and product.
• Build productive relationships with benefits brokers and consultants who can introduce the product to employers and help advance active opportunities.
• Represent the company at industry conferences, events, and prospect meetings across the Northeast, using those opportunities to create relationships and pipeline.

What success looks like in year one

• A qualified pipeline of employers with 500 to 5,000 employees, built through self-sourced outreach, marketing, events, and broker introductions.
• Multiple employer agreements signed and launched.
• Productive broker and consultant relationships that generate recurring employer introductions.
• Deals you can lead independently from first meeting through signature.
• A repeatable territory plan and sales approach informed by what resonates with buyers.
• An accurate forecast and clean implementation handoffs after signature.

What they are looking for

• Five or more years of quota-carrying B2B sales, with a track record of opening and closing new business.
• Direct experience selling employee benefits. You know how Total Rewards and Benefits leaders buy, who else sits in the decision, and how to position your benefit into the organization's broader wellbeing strategy.
• Full-cycle ownership. You've sourced pipeline, run discovery, built the business case, and closed deals to consistently hit or surpass quota.
• You're comfortable selling as a new benefit in the space. You can run a credible conversation without a finished case-study library or a solutions engineer in the room.
• A high-ownership, low-ego approach. You create momentum without waiting for direction, hold yourself to a high bar, share what works, and step in wherever the team needs you.
• Comfortable adopting new technology and using AI-powered sales tools to research accounts, personalize outreach, prepare for meetings, and manage opportunities more effectively.

Job-3682827

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