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Make Us Part of Your Team
Our Experience

CTO Teammate has sought to work with companies looking for a partner, not just a vendor.  We have conducted over 200 technology assessments in organizations ranging from angel-funded started-ups to $500M+ annual revenue public companies.  Additionally, we serve as Fractional CTOs or CIOs across Healthcare, Technology-Enabled Businesses, and Business Management Systems. 


We have a team of Chief Technology Officers (CTO), Application Architects, Software Engineers, AWS and Azure Infrastructure Engineers, and Information Security Professionals we bring in on projects as needed.  


 Our team's skills range across many aspects of business and technology with areas of expertise in

  • CTO and CIO Leadership

  • Cloud-Based Software Product Engineering

  • Product Management

  • Merger Technology Integration

  • Divestiture Technology Separation

  • Agile Software Development

  • Technology Team Transformation

  • Legacy Technology Retirement 

  • Complex Technology Program/Projects

  • Information Security

Domains of Expertise

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  • Healthcare Providers

  • Telemedicine 

  • Healthcare Informatics

  • Healthcare billing

  • Software Medical Devices

  • Hardware Medical Devices

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Technology Enabled Business

  • Product Strategy and Vision

  • Product Competitive Analysis

  • Product Road Map Process

  • Agile Product Ownership

  • Enterprise Level Technology Strategy and Governance

  • Software Platform Performance Engineering and Hardening

  • Data Center  Migrations 

  • Fault Tolerant/Self Healing Platforms

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Business Management Systems

  • Enterprise Resource Planning  (ERP)

  • Client Relationship Management (CRM)

  • Workflow Management Systems

  • Document Management Systems

  • Content Management Systems 

  • Finance and Accounting  Systems

  • Project Management Systems

  • Quality Management  Systems

We Speak Business and Technology

CTO Teammate understands the importance of business objectives and obligations.  We believe technology should be enabler of the overall organization and its goals.  We are equally fluent in terms such as EBITDA, ROI, IRR, EPS, Strategic Planning, and Turnarounds as we are in Service Oriented Architectures, REST-based integration layers, Agile Development, and N+1 redundant technology stacks.

Easy Working Relationship

Our services are primarily delivered remotely with regular onsite working sessions.  We try to make the partnership seamless and convenient.  We prefer to fix price our services by the project or a weekly rate including all of our expenses.  No hours to audit, no travel costs to review, just a value-oriented professional fee.

Our Technology Management Team
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Rick Jennings
Owner | Board Member

For the over15 years, Rick has provided CTO leadership for technology-enabled companies using proprietary software platforms. Rick’s areas of specialty include software engineering, high-availability technical architecture, technology platform operations, and customer services.  Rick has an Engineering Degree from the University of Texas and a Management degree from Stanford.   He used this experience to found CTO Teammate and develop our proprietary Technology Management Practices and Work Products. 

Rick is currently full time on an opportunity and his involvement is limited to Board Memberships he holds and  limited strategic conversations with CTO Teammate Clients.

Highlights of his background are: 

  • Board of Directors, Several Technology Firms

  • Fractional CTO to series of satisfied clients

  • CTO, Staywell

  • CIO and CTO, Virtual Radiologic . 

  • Managing Director, Assess IT

  • Vice President, Computer Sciences

  • MS Management, Stanford

  • BS Engineering, Texas 

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Ross Caleca
Principal Consultant  |  Partner

Over the last 12 years Ross has provided strategic business and technology leadership and advising roles for early growth start-ups and established technology enabled companies.  Areas of focus include business management, process engineering, and  incorporation of data analytics into business workflows and offerings.  Ross holds a B.S. in Biology from the UCSD, and an MBA from the Rady School of Management at UCSD.

Ross provides the daily management of CTO Teammate and our team of Fractional CTOs, Software Architects, Software Developers, and Data Scientists. 

Highlights of his background are:

  • Managing Partner, American Essential

  • Director of Operations, MD Revolution

  • Program Manager, Vituity

  • MBA, Rady School of Management at UCSD

  • BS Biology, UCSD

Interested in joining the team? Reach out​

Some of Our Clients

Need more details? Contact us

We are here to assist. Contact us by phone or email.

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