Vice President, Professional Services

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

As the Vice President of Professional Services, you will be the primary architect of DailyPay’s implementation strategy, responsible for maturing a predictable, outcome-driven organization that leverages AI and autonomous workflows to scale with rapid growth. You will provide executive leadership to a multi-tiered team, driving frictionless onboarding and technical integration frameworks that ensure long-term stability and operational risk reduction. By partnering across Client Success, Sales, Product, Engineering, and Operations, you will transform the implementation lifecycle into a competitive advantage, directly accelerating time-to-revenue and fostering deep-seated client trust.

Key Responsibilities

• Strategic Leadership: Define the high-level vision and governing policies for the Professional Services and Solutions Engineering segments to ensure company-wide impact and operational excellence. Champion an AI-first, agentic service delivery model, identifying opportunities for autonomous agents to handle routine configurations, mapping, and testing.

• Organizational Maturity: Strengthen leadership depth and standardize delivery frameworks to create a predictable, scalable organization capable of supporting rapid growth.

• Risk & Stability: Drive accountability for integration stability and operational risk reduction, ensuring seamless integrations through the deployment of self-healing agentic workflows that continuously identify and resolve integration anomalies before they impact the client.

• Revenue Acceleration: Optimize the implementation engine to further decrease client time-to-value across Strategic, Enterprise, and SME segments through improved tooling and process refinement.

• Executive Advocacy: Serve as the principal advisor to the executive team on the implementation function and in high-stakes client and internal stakeholder meetings.

• Cross-Functional Alignment: Orchestrate tight alignment with Client Success, Sales, Product, Engineering, and Operations to ensure Professional Services serves as a trusted partner throughout the customer lifecycle.

• Product Influence: Advocate for client and team needs within the organization to drive product roadmap improvements, including technology and AI capabilities, that simplify, accelerate, and enrich technical integrations.

• Performance Governance: Govern key performance indicators (KPIs) and reporting structures including client launches; actuals and forecast, time-to-launch, implementation / re-implemention incidents, and functional HC utilization.
  

Qualifications

• Executive Experience: 10+ years of professional services experience, with a proven track record of leading large-scale technical implementation teams and driving AI or intelligent automation transformations in a SaaS or Fintech environment.

• Strategic Vision: Demonstrated ability to navigate high-stakes ambiguity and define systemic strategies that align with broader organizational goals.

• Technical Acumen: Deep understanding of HCM and/or payroll/timekeeping systems technical integrations, migrations, and the Solutions Engineering lifecycle. Familiarity with the application of Large Language Models (LLMs), AI agents, and intelligent automation in B2B2C service delivery is highly preferred.

• Leadership Depth: Exceptional ability to develop senior leaders and manage large-scale resources, including a workforce of 40+ members.

• Communication Excellence: Sophisticated communication skills with the capacity to influence stakeholders and reconcile multiple executive perspectives.

Academic Foundation: Bachelor’s degree in a related field or equivalent professional experience at the executive level.

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

• 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 View email address on us.fitly.work. 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.