Account Executive, Small-to-Medium Enterprise

DailyPay; United States; On-site; USD 90,000 - 140,000; Full time

Benefits offered by this job

Health, vision, and dental insurance

Equity ownership

Life and AD&D, disability coverage

Employee Assistance Program

401K with company match

Unlimited PTO

Job summary

DailyPay is expanding its sales organization and seeks an SME Account Executive to drive net new business in the 500–2,000 employee segment. You will own the full sales cycle from outreach to close, position DailyPay as a product expert, and build relationships with HR, Finance, and Ops leaders.

You will leverage data-driven storytelling to demonstrate ROI and retention improvements, conduct high-impact demonstrations, and partner with Sales Development and Implementation teams to ensure

Qualifications

• 3+ years in B2B SaaS sales with quotas
• Ability to build relationships with stakeholders
• Strong presentation and data-driven storytelling

Responsibilities

• Own full-cycle sales for SME segment (500–2000 employees)
• Deliver product demos via webinars and in-person meetings
• Build and maintain a robust pipeline using CRM and outbound prospecting
• Engage HR, Finance, and Operations stakeholders to build consensus
• Use analytics to present ROI and retention impact
• Negotiate terms and close agreements
• Collaborate with SDR and Implementation teams
• Stay informed on the HCM and Fintech landscape

Skills

B2B sales

SaaS

Consultative selling

CRM proficiency

Executive engagement

Tools

Salesforce

Salesloft

Job description

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The traditional pay cycle is outdated, and DailyPay is changing the game.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

• Full-Cycle Sales Management: Independently manage and execute sales cycles for companies within the SME segment (500–2,000 employees) to meet or exceed monthly quotas.
• Strategic Presentation: Conduct high-impact product demonstrations via webinars and in-person meetings, effectively articulating the DailyPay value proposition to prospect champions.
• Pipeline Development: Proactively build and maintain a robust pipeline of qualified opportunities using modern sales tools (Salesforce, Salesloft) and outbound prospecting techniques.
• Stakeholder Navigation: Identify and engage with key influencers and decision-makers across HR, Finance, and Operations departments to build consensus.
• Data-Driven Consulting: Utilize DailyPay’s analytical tools to present clear business cases, highlighting employee benefit ROI and retention improvements for partners.
• Contract Negotiation: Manage and facilitate the negotiation of service terms and agreements with prospect decision-makers, ensuring alignment with company guidelines.
• Cross-Functional Collaboration: Partner with Sales Development and Implementation teams to ensure a seamless transition of accounts and long-term partner success.
• Market Intelligence: Maintain up-to-date knowledge of the HCM and Fintech landscape to effectively handle objections and position DailyPay against competitor

What You Bring to The Team:

• Proven Sales Track Record: 3+ years of experience in B2B sales (SaaS, HR technology, or financial services preferred), with a history of meeting or exceeding quotas.
• Consultative Skills: Demonstrated ability to build trust with stakeholders and navigate mid-market corporate structures.
• Communication Excellence: Strong verbal and written communication skills, with professional fluency in presenting technical product features to non-technical audiences.
• Analytical Mindset: High level of business acumen with the ability to interpret data and use financial tools to communicate value.
• Operational Discipline: Exceptional detail orientation and organizational skills, specifically regarding CRM hygiene and pipeline management.
• Adaptability: A coachable, resilient mindset with the ability to thrive in a fast-paced environment and adapt to evolving sales strategies

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 [e-mail]. 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.