Vice President, Professional Services

About Us:
DailyPay is the leader in On-Demand Pay, helping employers modernize how people get their pay. DailyPay serves more than 1,900 employers and over 6 million employees, including many of the world's most recognized brands. By providing real-time access to earned pay and financial wellness tools, DailyPay helps employees manage their finances and helps employers attract and retain talent. DailyPay is helping define the future of pay, where money moves at the speed of work.. Learn more at DailyPay's Press Center.

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.

• →

  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.
  

• 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.