Director, Large Enterprise Sales

About the role

DailyPay is seeking a high-impact Director of Large Enterprise Sales to lead a team focused on acquiring new enterprise logos within the 5,000–20,000 employee market segment. This leader will drive a disciplined, consultative, and highly strategic sales motion focused on complex enterprise organizations with long sales cycles, multiple stakeholders, and sophisticated procurement processes.

Responsibilities

• Lead and coach a team of Large Enterprise Account Executives focused on acquiring net new enterprise customers within the 5,000–20,000 employee segment
• Drive disciplined pipeline generation, strategic account planning, and execution across complex enterprise sales cycles with multiple stakeholders and long procurement processes
• Ensure consistent execution of MEDDPICC, Sandler, and consultative sales methodologies throughout the sales process
• Build a culture of accountability, operational rigor, forecasting accuracy, and performance excellence through regular pipeline reviews, deal coaching, and performance management
• Coach sellers on enterprise discovery, executive engagement, multi-threading, negotiation strategy, objection handling, and value-based selling
• Partner cross-functionally with Legal, Security, Finance, Product, Marketing, and Customer Success teams to remove deal blockers and accelerate strategic opportunities
• Elevate the team’s ability to deliver compelling executive-level storytelling and business cases tied to workforce outcomes, ROI, and financial wellness impact
• Support strategic relationship management within existing enterprise customers to strengthen partnerships and identify expansion opportunities

Requirements

• 10+ years of enterprise SaaS, fintech, HCM, payroll, or related technology sales experience, including 3–5+ years leading high-performing enterprise sales teams
• Proven success selling into and leading teams focused on enterprise organizations with 5,000–20,000 employees
• Demonstrated experience managing complex enterprise sales cycles involving executive buyers, procurement, legal, security, and multiple decision-makers
• Strong expertise in MEDDPICC, Sandler, and consultative enterprise sales methodologies, with a track record of improving team execution and sales performance
• Proven ability to coach, develop, and hold enterprise sales teams accountable while fostering a high-performance culture
• Exceptional executive communication, relationship-building, and storytelling skills, with the ability to articulate business value and differentiate within competitive enterprise environments

Qualifications

• Not specified

Skills

• Not specified

Benefits

• Not specified

Pay

• $163K - $250K

Schedule

• Not specified