Hi, my name is

Nathan Anderson

Fractional CTO for Series A & B Startups

You’ve raised your round. Now you need a CTO who can build the team, ship the product, and establish the architecture — without the full-time executive cost.

I embed with Series A and B startups as Fractional CTO or VP Engineering and get to work immediately. I’ve taken a healthcare platform from idea to launch — product roadmap, architecture, and acquisition strategy. I’ve helped a FinTech team go from one release per quarter to multiple releases per week by rebuilding their CI/CD pipeline, team structure, and SDLC.

25+ years leading engineering at Rackspace, ClearDATA, Chargify, and SWIVEL. Deep expertise in Healthcare Tech and FinTech.

Let’s talk →

About

Series A and B startups hire me when they need executive-level tech leadership but aren't ready — or funded enough — for a full-time CTO.

I step in as Fractional CTO or VP Engineering and help you build the team, establish the architecture, and ship the product. I specialize in **Healthcare Tech** and **FinTech** — industries where compliance, security, and speed all matter at once.

With 25+ years at companies like Rackspace, ClearDATA, Chargify, and SWIVEL, I've seen what separates engineering orgs that scale from ones that stall. I bring that pattern recognition directly to your team.
Core Competencies
  • Technology Strategy & Vision
  • Engineering Leadership
  • Cloud Architecture (AWS, Azure, GCP)
  • Software Development
  • Cybersecurity & Compliance
  • Digital Transformation
  • Team Building & Mentoring
  • Product Development

Experience

Chief Technology Officer & Chief Product Officer - Alenio Health
2025 - Present
  Leading technology and product strategy for an early-stage healthcare tech startup launching in Mexico.
  - Defining product roadmap and go-to-market strategy for initial launch
  - Establishing architecture and engineering foundation for the platform
  - Driving product vision from concept through market launch
Fractional CTO - Nathan Anderson Consulting
April 2024 - May 2025
  Embedded as Fractional CTO and VP Engineering for post-revenue startups navigating growth and technical complexity.
  - Took a Healthcare Tech platform from idea to launch — built product roadmap, initial architecture, and acquisition strategy
  - Helped a FinTech go from one release per quarter to multiple releases per week by rebuilding CI/CD pipeline, engineering team structure, and SDLC
  - Specialized in Series A and B companies in FinTech and Healthcare Tech
  - Delivered fractional CTO and VP Engineering services to multiple client companies simultaneously
Vice President of Software Engineering - SWIVEL
February 2023 - April 2024
  Reported directly to CEO and led Software Engineering organization through major growth and transformation initiatives.
  - Led organization through multiple major product launches and company acquisition
  - Executed complete Product & Engineering department reorganization into functional business units
  - Streamlined cross-functional communication and aligned organization-wide goals for accelerated product development
  - Organized and facilitated first company-wide Engineering in-person offsite planning event
  - Built SWIVEL's first DevOps function to reduce operational overhead on engineering teams
  - Conducted M&A due diligence for MagicWrighter acquisition and led integration planning
Chief Technology Officer - CyberFortress
February 2022 - February 2023
  Led global Product Engineering, Product Management, and Information Systems teams for a cybersecurity company.
  - Managed product portfolio roadmap and SDLC across multiple acquired brands
  - Unified engineering teams from Jungle Disk, LiveVault, KeepItSafe, and OffSiteDataSync acquisitions
  - Designed, developed, and delivered new products and features for consolidated portfolio
  - Established unified organizational structure and reporting for cross-brand teams
  - Managed vendor relationships and supported marketing initiatives through technical content
Vice President of DevOps and Engineering - Chargify (now Maxio)
July 2021 - February 2022
  Led global DevOps, Software Engineering, IT, and Compliance teams across multiple international locations.
  - Managed distributed engineering teams in Krakow and Warsaw, Poland with global sales & support in Dublin
  - Served as core team member for post-merger integration of Chargify and SaaSOptics
  - Led due diligence process during Battery Ventures acquisition of Chargify
  - Architected and developed combined product offerings from both Chargify and SaaSOptics platforms
  - Coordinated cross-functional teams across multiple time zones and regulatory environments
Director of Engineering and DevOps - Chargify (now Maxio)
January 2019 - July 2021
  Led Operations, Compliance, and Helpdesk functions for a global SaaS organization spanning multiple continents.
  - Managed world-spanning Operations department across San Antonio, Poland, and Australia
  - Oversaw all system operations and infrastructure for enterprise-scale billing platform
  - Led comprehensive compliance efforts including SOC I Type II, PCI DSS, and GDPR certifications
  - Served as primary point of contact for customer compliance meetings and audits
  - Developed and managed compliance policies and procedures across international jurisdictions
Director of Engineering - ClearDATA
December 2015 - January 2019
  Led distributed Engineering teams responsible for core components of HIPAA compliant hosting framework and enterprise microservice architectures.
  - Architected enterprise-scale microservice architectures and multi-cloud solutions on AWS
  - Led and mentored distributed engineering teams across multiple locations
  - Engaged directly with customers to understand product needs and demonstrate platform capabilities
  - Facilitated strategic roadmap planning and represented products at HIMSS and healthcare trade shows
  - Managed critical partner relationships and participated in AWS vendor confidential roadmap briefings
  - Ensured compliance and security posture of core products across SOC2, HITRUST, and other major audits
  - Developed AWS platform automation tools for healthcare-grade infrastructure
  - Represented Product Engineering in enterprise audit processes and regulatory compliance initiatives
Director of Product Management - Rackspace
September 2013 - December 2015
  Managed Product Management team responsible for Cloud Identity (OpenStack Keystone), Key Management (Barbican), and core cloud infrastructure services.
  - Led product management for usage processing and billing systems across the cloud platform
  - Represented Public Cloud division on major company-wide strategic initiatives
  - Helped launch Barbican as an official OpenStack project for key management services
  - Successfully launched Repose (openrepose.org) as internal developer toolkit for API development
  - Managed product roadmaps for various services and toolkits critical to cloud operations
  - Collaborated with engineering teams to deliver common API development solutions across all Cloud Engineering teams
Senior Product Manager - Rackspace
June 2010 - September 2013
  Led product management for billing & usage reporting systems and internal cloud infrastructure services.
  - Managed billing and usage reporting systems for enterprise cloud platform
  - Oversaw product development for various services internal to cloud infrastructure operations
  - Led development of tools utilized by Cloud Engineering teams for enhanced productivity
  - Managed team of Product Managers and Technical Product Managers
  - Collaborated with engineering teams to deliver critical infrastructure and tooling solutions
  - Established product management processes and frameworks for cloud services portfolio
Software Development Manager - Rackspace
June 2002 - June 2010
  Led development of Public Cloud Control Panel, internal management portals, and core cloud infrastructure services during Rackspace's transformation to cloud computing.
  - Managed development of Public Cloud Control Panel and various internal management portals
  - Led Cloud Servers API and Cloud Identity development initiatives
  - Architected internal systems and services necessary for large-scale cloud operations
  - Orchestrated monitoring system overhaul integrating OpenNMS, Nimbus, HP SiteScope, and HP NNM
  - Built large-scale event processing, de-duplication, and correlation engine for enterprise monitoring
  - Managed development of MyRackspace customer portal and Rackspace.com platform
  - Established foundational infrastructure for Rackspace's cloud services evolution
Software Developer - Rackspace
December 2000 - June 2002
  Developed foundational customer-facing platforms during Rackspace's early growth phase as a hosting company.
  - Led development of MyRackspace customer portal for managed hosting services
  - Built and maintained the public website rackspace.com
  - Established core web development practices and frameworks for customer-facing applications
  - Contributed to early hosting platform infrastructure and customer management systems
System Integrator - IPI GrammTech
1998 - December 2000
  Served as Systems Engineer performing diverse technical functions across government and commercial contracts.
  - Performed network and system administration across variety of government and commercial environments
  - Developed custom applications including Air Force Library System automation for book procurement processes
  - Installed and maintained point-to-point wireless network infrastructure in downtown San Antonio
  - Diagnosed and maintained legacy Solaris infrastructure and large-scale WORM drive array systems
  - Provided comprehensive network troubleshooting, installation, and technical support services
  - Gained foundational experience across multiple technologies, platforms, and industry verticals
System Administrator and Tech Support - InterSAT Internet
1996 - 1998
  Served as sole employee of a small ISP, performing comprehensive technical operations across all business functions.
  - Managed systems administration for both Windows and Linux servers as the only technical staff member
  - Provided technical support and customer service for growing customer base
  - Performed network engineering and infrastructure management for ISP operations
  - Developed custom software solutions to support business operations and customer management
  - Helped scale the business from 100 to over 3,000 customers during 18-month tenure
  - Gained comprehensive experience in all aspects of ISP operations and small business technology management

Contact

If you’re a Series A or B startup that needs experienced technology leadership without a full-time CTO hire, let’s talk. I work with companies in Healthcare Tech and FinTech.