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The traditional pay cycle is outdated, and DailyPay is changing the game.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.

• Own the full sales cycle for prospective clients with <1,000 employees, consistently achieving or exceeding quota

• 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

• 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