Account Executive, Small-to-Medium Enterprise

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.

The Role

The traditional pay cycle is outdated, and DailyPay is changing the game. We are the undisputed leader in On-Demand Pay, serving over 1,900 employers and 6M+ workers and we were just named the #1 Earned Wage Access provider!

Check out our CEO Nelson Chai’s LinkedIn post for the details.

To power this momentum, we are rapidly expanding our sales organization. The SME Account Executive is a dynamic, results-oriented sales professional responsible for driving net new business within the 500–2,000 employee segment. Reporting to the Sales Director, you will manage the full sales cycle from initial outreach to close, focusing on regional territory growth. You will serve as a DailyPay product expert, building foundational relationships with key stakeholders and leveraging data-driven insights to demonstrate how our platform solves critical business challenges for growing organizations.

How You Will Make an Impact:

• Own the full sales cycle for prospective clients with

• Build and maintain a healthy pipeline through outbound prospecting, account-based outreach, referrals, and strategic follow-up

• Conduct compelling product demonstrations and business discussions that clearly communicate DailyPay’s value proposition

• Engage and influence stakeholders across HR, Payroll, Finance, and Operations to drive consensus and executive buy-in

• Develop ROI-driven business cases using data and insights to support customer decision-making

• Lead contract negotiations and facilitate agreement execution in accordance with company guidelines

• Partner closely with Solution Engineers, Implementation Managers, and Client Success Managers to ensure a seamless customer launch and onboarding experience

• Attend industry conferences, networking events, and partner-led events at least quarterly to build relationships, generate pipeline, and represent the DailyPay brand

• Maintain knowledge of the HCM, Payroll, and Fintech landscape to effectively position DailyPay and address competitive challenges

What You Bring to The Team:

• 3+ years of successful B2B SaaS sales experience, preferably within HR, Payroll, HCM, HRIS, or related technology solutions

• Proven success in a predominantly outbound sales environment with a track record of self-generating pipeline and exceeding quota

• Familiarity with MEDPICC and Sandler sales methodologies

• Strong consultative selling, discovery, negotiation, and relationship-building skills

• Ability to communicate complex technical concepts to both technical and non-technical audiences

• Strong business acumen, analytical thinking, and experience building value-based business cases

• Highly organized with excellent CRM hygiene and pipeline management discipline

• Coachable, resilient, and adaptable in a fast-paced, high-growth environment

What We Offer:

• 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 aren't 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 don’t 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. We’ve 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, you’ll find it here.

If you require reasonable accommodation for any aspect of the recruitment process, please send a request to peopleops@dailypay.com . 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.