Director, Large Enterprise Sales

About Us:
DailyPay is transforming the way people get paid. As a worktech company and the industry’s leading on demand pay solution, DailyPay uses an award-winning technology platform to help America’s top employers build stronger relationships with their employees. This voluntary employee benefit enables workers everywhere to feel more motivated to work harder and stay longer on the job while supporting their financial well-being outside of the workplace.
DailyPay is headquartered in New York City, with operations throughout the United States as well as in Belfast. For more information, visit DailyPay's Press Center.

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.

The ideal candidate is a proven enterprise sales leader with deep experience building and coaching high-performing sales teams, driving accountability, and leading through structured sales methodologies including MEDDPICC and Sandler. This role requires a leader who can develop enterprise sellers into trusted advisors capable of uncovering business pain, navigating complex buying committees, building executive relationships, and delivering compelling business-value storytelling.

While the primary focus is net new logo acquisition, this leader will also ensure Account Executives maintain strong executive relationships within existing client accounts to support expansion opportunities, retention, and long-term strategic partnerships.

If this opportunity excites you, we encourage you to apply even if you do not meet all of the qualifications.

• 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

• 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