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The Director of Enterprise Sales provides strategic leadership to the Account Executive team to drive net-new revenue growth and market expansion. They serve as an executive escalation point for complex deals and ensure alignment across cross-functional teams.
Candidates must have at least 7 years of professional sales experience, including 3+ years in a B2B enterprise sales management role. A bachelor's degree and proficiency in Salesforce and modern sales technology stacks are required.
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 Director of Enterprise Sales provides strategic leadership to the Account Executive team, directly driving net-new revenue growth and maximizing DailyPay’s market expansion across key enterprise segments. Serving as a principal advisor and escalation point, this role reconciles complex stakeholder perspectives across multi-threaded enterprise deals to secure high-value partnerships. The Director establishes functional sales objectives, implements metrics-based management cultures, and aligns team execution with broader corporate growth targets. By cultivating a high-performance culture, this leader significantly impacts the competitive positioning and long-term operational effectiveness of the sales function.
Team Leadership: Recruit, develop, and manage a high-performing Account Executive team, focusing on continuous performance elevation and talent retention.
Strategic Deal Orchestration: Serve as the executive escalation point for complex enterprise prospects, designing innovative deal strategies to accelerate sales cycles.
Revenue Forecasting: Deliver highly accurate weekly, quarterly, and annual revenue forecasts to the VP of Sales, utilizing metrics-based management data.
Market Expansion: Define and execute tactical plans to maximize DailyPay's penetration across target market segments and enterprise verticals.
Cross-Functional Collaboration: Partner closely with Sales Operations, Marketing, Product, and Legal teams to ensure seamless alignment on go-to-market strategies and resource deployment.
Process Optimization: Develop, refine, and enforce scalable sales methodologies, playbooks, and value propositions tailored for complex financial technology solutions.
CRM & Tech Governance: Drive the strict adoption of CRM strategies, sales enablement technologies, and data analytics to optimize pipeline health and visibility.
Brand Advocacy: Serve as a principal market evangelist, educating the broader labor and corporate marketplace on the strategic benefits of DailyPay’s platform.
Proven Leadership: 7+ years of professional sales experience, with at least 3+ years successfully managing and scaling a high-performing B2B enterprise sales team.
Domain Expertise: Demonstrated track record of success selling complex SaaS, HR Tech, FinTech, or Enterprise Business Intelligence solutions.
Strategic Execution: Proven ability to translate high-level corporate goals into actionable sales plans, structured processes, and measurable revenue outcomes.
Advanced Tech Literacy: Exceptional proficiency utilizing Salesforce and modern sales tech stacks (e.g., Clari, Gong, Salesloft) for predictable pipeline management.
Stakeholder Management: Elite communication, negotiation, and public speaking skills, with a verified capability to influence and close deals at the C-suite level.
Educational Foundation: Bachelor’s degree in Business Administration, Marketing, Communications, or a related professional field.
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 [email protected]. 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.
The leader in on-demand pay and #1 adopted financial wellness benefit. Trusted by 1,000+ employers.
The leader in On-Demand Pay and #1 adopted financial wellness benefit. Because life doesn't wait and neither should your pay. Trusted by 1,000+ employers.
Offices: 55 Water St, New York, New York 10041, US · 60 South 6th St, 2800, Minneapolis, Minnesota 55402, US
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