Director, Large Enterprise Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead and mentor a team of Large Enterprise Account Executives dedicated to securing new enterprise clients within the 5,000–20,000 employee range.

• Foster disciplined pipeline development, strategic account planning, and execution across intricate enterprise sales cycles involving multiple stakeholders and extensive procurement processes.

• Ensure the consistent application of MEDDPICC, Sandler, and consultative sales methodologies throughout the sales journey.

• Cultivate a culture of accountability, operational excellence, forecasting accuracy, and high performance through regular pipeline assessments, deal coaching, and performance management.

• Guide sellers in enterprise discovery, engaging with executives, multi-threading, developing negotiation strategies, handling objections, and employing value-based selling techniques.

• Collaborate cross-functionally with Legal, Security, Finance, Product, Marketing, and Customer Success teams to eliminate deal hindrances and expedite strategic opportunities.

• Enhance the team's capability to present persuasive executive-level narratives and business cases connected to workforce outcomes, ROI, and financial wellness impact.

• Assist in managing strategic relationships with existing enterprise clients to reinforce partnerships and uncover expansion possibilities.

⛳️ Requirements

• Over 10 years of experience in enterprise SaaS, fintech, HCM, payroll, or related technology sales, including 3–5+ years in leadership roles with high-performing enterprise sales teams.

• Proven track record of selling to and leading teams focused on enterprise organizations with 5,000–20,000 employees.

• Demonstrated experience in managing complex enterprise sales cycles that involve executive buyers, procurement, legal, security, and various decision-makers.

• Strong proficiency in MEDDPICC, Sandler, and consultative enterprise sales methodologies, with a history of enhancing team execution and sales performance.

• Established ability to coach, develop, and hold enterprise sales teams accountable while promoting a high-performance culture.

• Outstanding executive communication, relationship-building, and storytelling abilities, with a knack for articulating business value and differentiating in competitive enterprise landscapes.

🏝️ Benefits

• Exceptional health, vision, and dental care.

• Opportunity for equity ownership.

• Life and AD&D, short- and long-term disability coverage.

• Employee Assistance Program.

• Employee Resource Groups.

• Enjoyable company outings and events.

• Unlimited PTO.

• 401K with company match.