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About the Role

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. This role serves as a principal advisor and escalation point, reconciling 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, significantly impacting the competitive positioning and long-term operational effectiveness of the sales function.

Responsibilities

Recruit, develop, and manage a high-performing Account Executive team, focusing on continuous performance elevation and talent retention.
Serve as the executive escalation point for complex enterprise prospects, designing innovative deal strategies to accelerate sales cycles.
Deliver highly accurate weekly, quarterly, and annual revenue forecasts to the VP of Sales, utilizing metrics-based management data.
Define and execute tactical plans to maximize DailyPay's penetration across target market segments and enterprise verticals.
Partner closely with Sales Operations, Marketing, Product, and Legal teams to ensure seamless alignment on go-to-market strategies and resource deployment.
Develop, refine, and enforce scalable sales methodologies, playbooks, and value propositions tailored for complex financial technology solutions.
Drive the strict adoption of CRM strategies, sales enablement technologies, and data analytics to optimize pipeline health and visibility.
Serve as a principal market evangelist, educating the broader labor and corporate marketplace on the strategic benefits of DailyPay’s platform.

Requirements

7+ years of professional sales experience, with at least 3+ years successfully managing and scaling a high-performing B2B enterprise sales team.
Demonstrated track record of success selling complex SaaS, HR Tech, FinTech, or Enterprise Business Intelligence solutions.
Proven ability to translate high-level corporate goals into actionable sales plans, structured processes, and measurable revenue outcomes.
Exceptional proficiency utilizing Salesforce and modern sales tech stacks (e.g., Clari, Gong, Salesloft) for predictable pipeline management.
Elite communication, negotiation, and public speaking skills, with a verified capability to influence and close deals at the C-suite level.

Skills

Salesforce
Clari
Gong
Salesloft
SaaS
HR Tech
FinTech
Enterprise Business Intelligence
Communication
Negotiation
Public Speaking

Location

New York City

Work Type

Full-time

Experience Level

Director
7+ years of professional sales experience
3+ years managing enterprise sales teams

Education Level

Bachelor’s degree in Business Administration, Marketing, Communications, or a related professional field.

Benefits

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

About the Company

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.

Equal Opportunity

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.