Chief Technology Officer in Milwaukee, Wisconsin at Health Payment Systems Inc

About Health Payment Systems, Inc. (HPS/PayMedix)
Health Payment Systems, Inc. (HPS/PayMedix) is redefining how people access and pay for healthcare. We bring together provider networks, payments and financing solutions, and industry partners to remove financial barriers and simplify the healthcare experience for everyone involved.

Our team is solving one of the biggest challenges in healthcare: the flow of money and information between providers and consumers. The work we do improves access, reduces financial stress, and is reshaping how healthcare works at its most fundamental level.

Our solutions include:

• HPS Network: a high-performing, independent provider network in Wisconsin that helps employers control costs while maintaining strong access to care.
• PayMedix: a national healthcare payments platform that pays participating providers in full for all allowed charges regardless of consumer cost-share. Members receive consolidated medical information and billing, and receive interest-free financing if they need it.
• TempoPay: a flexible healthcare benefit solution that gives eligible individuals a simple, predictable way to pay for care over time, with zero interest or fees.

Join us in our mission to make the healthcare payments experience simpler, more transparent, and more connected – so people can focus on getting care when they need it, not when they think they can afford it.

About the Role
We are hiring a Chief Technology Officer to lead and scale our technology organization during a pivotal phase of growth. You’ll be joining a company that has already surpassed $20M in annual revenue and is on a clear trajectory to exceed $50M in annual revenue over the next few years. This is an opportunity to join a business with real traction and significant growth momentum. You will own execution across our core technology platform, including payments infrastructure, data systems, and internal tools, with a focus on improving velocity, reliability, and scalability.

We are looking for a product-minded technology leader who thinks beyond systems and infrastructure, and understands how technology decisions directly impact customer experience, revenue growth, and long-term market differentiation. We value a builder mentality and at this stage of the company, success will come from a leader who knows how to scale from 1 to 10 by operationalizing and maturing products for growth, reliability, and scale. You should bring new ideas and a forward-looking perspective, including the ability to evaluate and introduce AI and other emerging technologies where they drive real business value. You will help guide how the company evolves as technology advances, balancing innovation with practical execution.

This is a hands-on role for a leader who can operate across architecture and delivery, drive execution in complex environments, and build structure and momentum across teams. This role reports directly to the CEO and operates in a remote work environment.

Primary Responsibilities

• Engineering Execution & Delivery: Own end-to-end delivery across internal tech teams and external development vendors, driving consistent sprint execution, predictable releases, and high-quality output.
• Platform & Architecture: Lead the evolution of platform architecture to support scale, ensuring systems are modular, maintainable, and built for long-term growth.
• Team Building & Leadership: Build and lead a high-performing engineering organization with clear ownership, strong accountability, and a focus on outcomes.
• Data, Integrations & Infrastructure: Oversee integrations, data pipelines, and infrastructure to ensure reliability, scalability, and seamless support of internal and external systems.
• Security & Compliance: Ensure systems meet healthcare, financial, and enterprise security standards, including HIPAA, HITRUST, SOC 2, and other relevant regulatory and audit requirements, while maintaining strong data integrity, privacy, and security practices.
• AI Innovation,Transformation& Safety: Define and lead the AI roadmap, identifying high-impact opportunities and driving practical, scalable adoption that improves operational efficiency, customer experience, and business performance.
• Technical Strategy & Thought Leadership: Act as a strategic partner to leadership, setting clear technology direction and pushing initiatives forward with urgency, ownership, and a bias for action.
• Refactoring, Replatforming, Rebuilding: Lead the migration from legacy systems to modern, flexible, scalable, and resilient operating environments, including evaluation and replacement of existing vendors, data migration, system cutovers, and parallel run strategies, ensuring continuity across critical operations and minimizing risk to the business. The current technology environment includes Two On-Prem-Vendor-Hosted/Managed redundant data centers, Microsoft Azure for cloud infrastructure and hosting, .NET / C# powering core backend services, and React across the frontend application layer.

Required Qualifications

• 10+ years leading technology teams, including direct management of internal engineering teams and oversight of external development vendors or partners.
• Proven track record building and scaling engineering teams, products, and platforms from 0 to 1 and 1 to 10 in high-growth entrepreneurial or intrapreneurial environments, turning early-stage products into secure, reliable, high-volume production systems.
• Experience leading technology in health tech, fintech with a focus on payments, or other data-intensive environments where platform reliability, security, compliance, and data integrity are core to the business. Deep familiarity with payment orchestration, ledgering systems, money movement infrastructure, and leading vendors within the payments ecosystem is highly preferred.

Key Attributes for Success

• Cultivates Innovation: Drive innovation by building scalable systems and embedding AI-driven capabilities into core business workflows to accelerate growth, efficiency, and competitive advantage.
• Cross-Functional Team Collaboration: Drive alignment and collaboration across Product, Engineering, and Operations by translating complex technical work into business outcomes, while exercising strong judgment and building trust with stakeholders.
• Build & Lead High-Performing Teams: Ability to build, lead, and manage high-performing internal and external development teams, attract top technical talent as the company scales, and make thoughtful decisions on performance, retention, and team composition while fostering ownership and growth.
• Business-Minded Product Leadership: Demonstrates the ability to think beyond engineering execution and infrastructure, and deeply understands how technology, product decisions, and platform investments translate into better customer experiences, stronger revenue outcomes, and sustainable market differentiation.
  

Other Important Details

• Compensation:

• Base salary range: $230,000 - $265,000, depending on experience
• Equity: Offered
• Benefits: medical, dental, vision, HSA with company contribution,401(k)/Roth with company match, unlimited PTO and more.

• Hybrid Work:

• This is a remote position with travel as needed.

• Equal Opportunity & Workplace Environment:

• We are an equal opportunity employer and are committed to fostering an inclusive workplace where all employees can thrive. We consider applicants for employment without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other protected characteristic under applicable law. Reasonable accommodations will be provided to qualified individuals with disabilities throughout the hiring process and during employment.

• This role is primarily performed in a professional office environment and typically involves working at a desk using a computer, phone, and other standard office equipment. The position requires regular communication with colleagues and stakeholders through phone, video, and written channels, as well as the ability to perform work using a computer. The role may also involve occasional movement around the office. Additional hours may occasionally be required to support key projects or business needs.