Account Executive – Mid-Market

No Commission Cap. Build Relationships. Solve Business Problems. Expand Access to Healthcare.

Department: Sales

Compensation: $75,000 Base Salary + $75,000 Target Commission ($150,000 OTE) | Uncapped Commission

THE IMPACT YOU’LL MAKE…

As a Mid-Market Account Executive, you’ll own the sales process from qualified opportunity through close, helping mid-sized organizations deliver accessible and affordable healthcare to their employees.

You'll work with business owners, HR leaders, benefits decisionmakers, and other stakeholders to understand their workforce challenges, demonstrate how Direct2Care can help, and guide them toward the right solution.

This isn't about simply pitching a product. We're looking for someone who can listen, uncover business needs, build trust, navigate multiple stakeholders, and confidently move opportunities forward.

If you love consultative selling, take ownership of your pipeline, and are energized by winning new business while solving meaningful customer problems, we'd love to meet you.

YOUR DAY-TO-DAY IMPACT…

• Manage complex, multi-stakeholder sales cycles from discovery through negotiation and close.

• Understand prospect needs, workforce challenges, and goals to deliver tailored Direct2Care solutions.

• Build relationships with key decisionmakers, navigate stakeholders, and confidently address objections.

• Partner with SDRs and Marketing while generating new opportunities through strategic prospecting.

• Maintain a healthy pipeline, accurate forecasts, and sales activity in HubSpot.

• Consistently meet or exceed new business, revenue, and sales goals.

• Communicate Direct2Care's value through compelling presentations, product demos, and business cases.

• Position Direct2Care as a strategic partner by connecting our solutions to customer needs.

• Collaborate with Customer Success to ensure smooth transitions, documenting customer goals, expectations, and commitments while supporting long-term relationships.

• Share market insights and customer feedback with Product, Marketing, Customer Success, and leadership.

WHAT YOU’LL BRING TO THE TABLE…

• Bachelor's degree or equivalent professional experience.

• 3-4 years of B2B sales experience, preferably in a full-cycle or closing role, with a proven track record of meeting sales goals.

• Experience with discovery calls, presentations, product demos, and negotiations.

• Strong pipeline management, forecasting, and CRM skills; HubSpot is a plus.

• Excellent communication, presentation, and relationship-building skills with key decision makers.

• Strong business acumen and ability to manage multiple opportunities simultaneously.

• Self-motivated, organized, and accountable with a strong sense of ownership.

• Prior HubSpot usage preferred but not required.

YOU'LL THRIVE HERE IF YOU ARE...

• A consultative, goal-driven seller who listens, asks thoughtful questions, and builds trust.

• Competitive, persistent, and motivated to exceed expectations.

• Organized, accountable, and intentional about managing your pipeline.

• Adaptable, coachable, and comfortable in a fast-paced, growing environment.

• Collaborative and passionate about making a meaningful impact on businesses and their employees.

NICE TO HAVE…

• Experience selling SaaS, healthcare, employee benefits, HR technology, or B2B services.

• Experience selling to business owners, HR leaders, or executives and navigating multiple stakeholders.

• Familiarity with HubSpot or similar CRM platforms.

• Experience in a growth-stage organization.

YOUR TOOLKIT…

HubSpot, Microsoft Suite, Zoom, Teams, Notion, and sales prospecting and presentation tools.

WHAT SUCCESS LOOKS LIKE…

• Consistently meet or exceed new business and revenue goals.

• Maintain a healthy pipeline with accurate forecasts.

• Lead effective discovery calls, presentations, and product demonstrations.

• Navigate objections, negotiations, and key decisionmakers with confidence.

• Convert opportunities into long-term customers through strong relationships and seamless Customer Success handoffs.

• Take ownership of results and continuously improve your sales approach.

WHY YOU'LL LOVE WORKING HERE…

We believe great work happens when people are trusted, supported, and given room to grow.

Here's what you can expect:

• Competitive Pay: Base salary + uncapped commission with strong earning potential.

• Hybrid Flexibility: In-office collaboration Tuesdays and Thursdays.

• Remote Summers: Work remotely from June through September.

• Great Benefits: Comprehensive medical, dental, and vision coverage.

• Meaningful Work: Make a real impact at a growing, mission-driven company.

• People-First Culture: A collaborative team built on trust, ownership, and continuous learning.

• Room to Grow: Opportunities to develop your career as Direct2Care continues to scale.

Direct2Care is an equal opportunity employer. Direct2Care does not discriminate against applicants or employees based on any characteristic protected by applicable federal, state, or local law. We are committed to making our workplace inclusive and accessible. When someone needs support to do their best work, we take that seriously and work together to find a solution.