John Chipps

Lead technology strategy, platform evolution, and execution for a cloud-native healthcare fintech focused on payments, financing, and affordability across the dental industry. Key outcomes: • Scaled platform adoption to 2,500+ healthcare practices (approaching 2,800) • Built platform supporting $1.5B+ in annual payment volume • Launched WellfitPay and expanded platform capabilities • Expanded the platform across three product lines: payments, a financial marketplace, and dental membership plans • Established and manage strategic processing, banking, and integration partnerships, including Worldpay as primary payment processor • Grew the technology organization from 11 to 60+ FTEs across engineering, architecture, data, QA, DevOps, security, and analytics, with strong retention • Led technology strategy and diligence supporting growth financing and investor engagement • Drove AI-first engineering transformation, embedding AI into development workflows, fraud and anomaly detection, and customer-facing platform capabilities, with measurable governance and velocity outcomes • Modernized platform architecture on Azure, .NET, Databricks, and Microsoft Fabric I partner with executive leadership and the board to align platform strategy with growth, scalability, and enterprise value creation, operating at the intersection of technology, product, and business. Our work is ultimately about improving financial access and outcomes in healthcare, enabling practices to deliver care and patients to afford it.

Served as Board Chair of a federally insured credit union, providing fiduciary oversight across enterprise strategy, governance, risk, compliance, cybersecurity, and executive leadership. Led the board through a successful, member-approved strategic merger with Texans Credit Union that closed in 2026, including rigorous regulatory diligence, third-party and vendor continuity, member and employee communications, and executive oversight through transaction close. Provided governance oversight on technology, cybersecurity, and complex enterprise third-party relationships including Mary Kay, Signet Jewelers, and The Container Store. Partnered with the CEO and executive team to strengthen governance discipline, guide long-range strategic planning, and enhance institutional resilience and member value through a period of material transition. Previously served as Vice Chair, supporting leadership continuity, succession planning, and overall board effectiveness.

Recruited as a strategic technology advisor, appointed CIO, and subsequently promoted to CRO, leading both digital transformation and go-to-market execution for a high-growth auto fintech. As CIO and CRO, led technology, sales, and marketing, scaling the business from early-stage concept to a fully digital SaaS platform supporting 1,300+ active dealers with AI-enabled, vehicle-specific underwriting. Key accomplishments: • Built and scaled the platform from MVP to a robust Azure-based SaaS solution, incorporating data-driven and AI-enabled underwriting capabilities, enabling rapid market adoption • Drove 400% organizational growth, establishing offshore development and QA capabilities to support continuous delivery and scalability • Developed and executed product, technology, and go-to-market strategy to accelerate customer acquisition and expansion • Introduced new revenue streams and led strategic partner engagements to increase dealer adoption and retention • Engaged directly with investors and the board through Series A, B, and C fundraising, supporting diligence, investor strategy, and business development • Led implementation of core enterprise platforms including Azure, Salesforce, Dynamics, Databricks, and Power BI

Founded and led Seek CIO, an executive services firm delivering operating leadership to growth-stage, enterprise, and private equity-backed companies across fintech, healthcare, SaaS, restaurants, construction, and financial services. Over 12 years, personally served as interim or fractional CIO, CTO, CRO, and CEO across dozens of engagements, including full P&L ownership in select roles. Partnered with executive teams and boards to align business and technology strategy, scale platforms, and drive operational and revenue outcomes. Representative clients include Early Warning Services, TitleMax, F&I Express, Car Capital Technologies, Ignite Restaurants, Rogers O’Brien Construction, Texas Land & Cattle, Women’s Foodservice Forum, and AAPL. Key focus areas: • Served as interim CEO, CIO, CTO, and CRO across fintech, healthcare, SaaS, and enterprise environments • Full P&L ownership in select engagements, including revenue, operations, and organizational leadership • Led digital transformation and platform modernization programs for PE-backed and growth-stage companies • Built go-to-market motions, revenue models, and commercial partnerships alongside technology strategy • Advised boards and executive teams on technology governance, risk, and capital markets readiness • Designed organizational structures, built leadership benches, and led executive hiring • Evaluated and negotiated enterprise platform, vendor, and partner relationships

Established in 1956, the American Association of Professional Landmen is a professional organization that unites around 17,000 Landmen and land-related persons through professional development and services. AAPL serves as the voice of the Landman profession and continually seeks to foster industry cooperation through proactive legislative advocacy and leadership development. I directed all technology operations and formulated / implemented a digital technology strategy that eliminated instability while increasing functionality. • Spurred migration to cloud-based solution for member accounts, learning/certification systems, and performance management platforms into an integrated, seamless infrastructure. Reduced overall operations costs by 25% and increased member engagement by 20%. • Architected enterprise data model and optimized processes and information flows for 16,000 Oil and Gas professionals. • Selected and implemented mobile apps, online communities, job board, e-commerce, CMS, SFA and Backoffice platforms.

As CEO of Institution Solutions and Alloy Insurance Partners, led and managed all aspects of the businesses, with full P&L responsibility across insurance TPA (third-party administrator) operations, Credit Union Service Organization (CUSO) launches, and supporting technology platforms. Key accomplishments: • Managed the insurance TPA business for marquee insurance partners including Chubb and Prudential • Launched multiple insurance CUSOs enabling credit unions across the United States to offer, sell, and service a full suite of insurance products • Led the implementation of new products, client programs, and technology across the combined organization • Negotiated, implemented, and led strategic partnerships and commercial relationships driving organizational growth and expansion This role combined hands-on CEO-level P&L ownership with regulated financial services operations across insurance and credit union channels.

Engaged as Consulting CTO for the largest leadership development organization serving the foodservice industry, the second largest private employer in the United States. Reported directly to the CEO and Board of Directors on business metrics, technology strategy, and organizational initiatives, following successful execution of an initial technology audit and strategy. Key accomplishments: • Accountable for technology staff, budget, vendors, and special projects, including the buildout of WFF’s competency model and assessment platforms • Administered all marketing, registration, and events technology supporting 40+ annual national events, including the WFF Annual Conference and Executive Summit • Led deployment of new platforms including mobile and native applications, online communities, e-commerce, CMS, AMS (iMIS), SFA, and back-office systems • Planned and executed SSO and custom integrations across third-party platforms and systems • Delivered 22,000 engaged member connections (50% growth) and 15 million touchpoints (1,500% growth) • Guided and coached volunteer committees including the Technology Advisory, IT and Social Learning, and Online Communities Committees

Xpressdocs is an Internet-based provider of high quality, on-demand marketing programs and services. The company’s primary business is direct mail and digital marketing via web-enabled print solutions which allow users to quickly and easily design and produce high quality flyers, postcards, brochures, emails and other marketing materials with a rapid turnaround time. Acquired by Reynolds and Reynolds.

Batrus Hollweg International (BHI) is a human capital consulting firm specializing in pre-employment assessment and people development. As Sr. Vice President I was responsible for managing the company’s IT, sales, research, customer service, survey, hourly and management assessment and development business. Acquired by Kenexa and IBM.

Co-founded two companies in parallel: Webuilder: Consulting firm offering development, networking, and database services to Dallas/Fort Worth businesses. Client base included GTE, Manpower, and IPAccess. Netcounselors: SaaS platform for licensed mental health professionals to deliver online counseling services, positioned as “mental health at your fingertips.” Company was acquired by a consortium of psychologists.