Account Executive - Director - Remote Eligible

Account Executive - Director

We are seeking a highly driven and strategic Account Executive - Director to lead complex, high-value sales engagements in a fast-growing, high-impact environment. In this role, you will be responsible for building your own pipeline, executing disciplined sales cycles, and closing large multi-stakeholder deals that drive measurable business outcomes. You will navigate executive-level decision makers, develop compelling business cases, and manage procurement and contracting workflows end-to-end. This position offers significant autonomy and accountability, with the opportunity to influence both revenue growth and customer adoption strategies. The ideal candidate thrives in a fast-paced, partner-driven environment, and is motivated by challenging, outcome-focused targets. Success will be measured by pipeline creation, predictable quota attainment, and the ability to consistently close complex deals.

Accountabilities:

• Personally source and build pipeline through consistent outbound activity, targeting priority accounts and buyer personas
• Lead complex, high-value sales cycles from first touch through close, navigating executive buying committees and multi-stakeholder decisions
• Develop clear business cases, ROI narratives, and persuasive presentations for senior stakeholders
• Manage end-to-end deal execution, including procurement, legal, security, and contracting processes
• Maintain CRM hygiene, accurate pipeline visibility, and forecast reliability
• Collaborate cross-functionally to ensure smooth deal progression and stakeholder alignment
• Model professional sales execution and mentor team members on best practices

Requirements:

• 7–10+ years of enterprise SaaS sales experience, with a track record of closing large, complex deals
• Demonstrated success generating pipeline via outbound, not just inbound leads
• Strong organizational skills and experience tracking performance against contractual commitments
• Comfortable leading product demos, handling objections, and engaging senior executives
• Exceptional communication, negotiation, and presentation skills with the ability to influence without direct authority
• Experience with partner-led or channel sales, financial wellness, retirement, or employee benefits domains preferred
• Familiarity with Salesforce, partner portals, and enablement tools
• Ability to thrive in a high-growth startup environment with evolving processes
• High accountability, resilience, and a bias toward action, focused on outcomes over titles

Benefits:

• Competitive salary with potential performance-based incentives
• Fully remote work with flexibility to manage your schedule
• Health, dental, and vision insurance coverage
• 401(k) plan with company match
• Opportunities for professional development, mentorship, and cross-functional growth
• Exposure to a fast-growing, high-impact sales organization with the ability to influence strategy and outcomes
• Collaborative and inclusive work culture supporting innovation, learning, and career advancement