Chief Technology Officer — Remote, AI-Driven Growth Leader

Health Payment Systems, Inc.; Milwaukee, Northern (WI, KY); Hybrid; USD 230,000 - 265,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

HSA with company contribution

401(k) / Roth with company match

Unlimited PTO

Job summary

Health Payment Systems, Inc. (HPS/PayMedix) is hiring a Chief Technology Officer to lead and scale the technology organization during a pivotal growth phase.

You will own the core platform, including payments infrastructure, data systems, and internal tools, driving velocity, reliability, and scalability. You will guide AI initiatives, transform architecture, and ensure security/compliance while balancing innovation with execution and growth.

Qualifications

• 10+ years leading technology teams.
• Experience scaling engineering teams and platforms in high-growth environments.
• Experience in health tech or fintech/payments with data-intensive systems.

Responsibilities

• Own end-to-end delivery across internal tech teams and external vendors.
• Lead platform architecture evolution to support scale and long-term growth.
• Build and lead a high-performing engineering organization with clear ownership and accountability.
• Oversee data pipelines, integrations, and infrastructure for reliability and scalability.
• Ensure security, compliance (HIPAA, HITRUST, SOC 2) and data integrity.

Skills

Tech leadership

Scaling teams

Payments fintech experience

Tools

Azure

.NET / C#

React

Job description

Health Payment Systems, Inc. (HPS/PayMedix) is hiring a Chief Technology Officer to lead and scale the technology organization during a pivotal growth phase.

You will own the core platform, including payments infrastructure, data systems, and internal tools, driving velocity, reliability, and scalability. You will guide AI initiatives, transform architecture, and ensure security/compliance while balancing innovation with execution and growth.