Director, Large Enterprise Sales

About Us:
DailyPay is transforming the way people get paid. As a worktech company and the industrys leading on demand pay solution DailyPay uses an award-winning technology platform to help Americas 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 DailyPays 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 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 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 teams 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 35 years leading high-performing enterprise sales teams

• Proven success selling into and leading teams focused on enterprise organizations with 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

• Exceptional health vision and dental care

• Opportunity for equity ownership

• Life and AD&D short- and long-term disability

• Employee Assistance Program

• Employee Resource Groups

• Fun company outings and events

• Unlimited PTO

• 401K with company match

High-performing cultures arent built in silos they thrive on partnership. At DailyPay we Commit Together to an inclusive professional environment where multifaceted perspectives are our greatest competitive advantage. We recognize that our team members dont live single-issue lives and we lean into the wide-ranging backgrounds and life stages that sharpen our collective decision-making.

In our high-trust environment we empower you to Challenge Norms. Weve created a space where it is safe to ask difficult questions disrupt the status quo and share bold perspectives without fear of professional fallout. We believe that by checking our own assumptions and staying curious about the experiences of others we arrive at better more innovative results.

We provide the space for you to do your best work through peer advocacy and transparent career development. If you are looking for a culture that values intellectual honesty celebrates the unique lived experiences of its people and thrives on collective success youll find it here.

If you require reasonable accommodation for any aspect of the recruitment process please send a request to . All requests for accommodation will be addressed as confidentially as practicable.

DailyPay is an equal opportunity employer. All qualified applicants will receive consideration without regard to race color religion or creed alienage or citizenship status political affiliation marital or partnership status age national origin ancestry physical or mental disability medical condition veteran status gender gender identity pregnancy childbirth (or related medical conditions) sex sexual orientation sexual and other reproductive health decisions genetic disorder genetic predisposition carrier status military status familial status or domestic violence victim status and any other basis protected under federal state or local laws.

Required Experience:

Director