Fractional CTO · Healthcare Tech & FinTech

Executive engineering leadership, at the size you actually need.

I embed with Series A and B startups as Fractional CTO or VP Engineering.

You’ve raised your round. The board wants a roadmap, your engineers want direction, and the architecture decisions you make in the next six months will either compound or haunt you.

I’ve taken a healthcare platform from idea to launch — roadmap, architecture, and acquisition strategy. I’ve helped a FinTech go from one release per quarter to multiple releases per week by rebuilding their CI/CD pipeline, team structure, and SDLC. I do that work part-time, starting immediately.

Based in San Antonio, Texas · Working remotely across the US and Mexico

Nathan Anderson, Fractional CTO

25+ years building and leading engineering teams at

  • Rackspace
  • ClearDATA
  • Chargify / Maxio
  • CyberFortress
  • SWIVEL

Track record

What that experience buys you

25+ years

Leading engineering, product and DevOps organisations — from a 3,000-customer ISP to global teams across three continents.

4 acquisitions

Due diligence and post-merger integration at Rackspace, Chargify, SWIVEL, and CyberFortress.

5 compliance regimes

SOC 2 Type II, PCI DSS, HIPAA, HITRUST and GDPR programmes led end to end.

1 per quarter → more than onde a day

Release cadence improvement delivered for a FinTech client by rebuilding CI/CD, team structure and SDLC.

Engagements

Executive engineering leadership, without the full-time hire

Three ways I embed with Series A and B teams. Most engagements start part-time and adjust as the work demands.

Fractional CTO

For companies with no technology executive, or a founding engineer who has outgrown the role.

  • Technical strategy, roadmap and architecture ownership
  • Build-versus-buy calls and vendor relationships
  • The technology story your investors and board need
  • Typically 1–3 days a week, reviewed quarterly

Fractional VP Engineering

For companies where the technical vision is clear but delivery is not.

  • Team structure, hiring plans and performance management
  • SDLC, CI/CD and the operating cadence that ships software
  • Turning a roadmap into predictable delivery
  • Typically 2–3 days a week, six months minimum

Diligence & compliance readiness

For companies raising, selling, or entering a regulated market for the first time.

  • Architecture, security and compliance posture review
  • Engineering team and delivery assessment
  • Remediation plan — before someone else finds the gaps
  • Four to six weeks, or ongoing advisory

Selected results

Problems I have already solved

Healthcare Tech

Idea to launched platform

Took a healthcare technology platform from concept to market as Fractional CTO — owning the product roadmap, the initial architecture, and the acquisition strategy that followed.

FinTech

Quarterly releases to weekly

Rebuilt a FinTech client's CI/CD pipeline, engineering team structure and SDLC, moving them from one release per quarter to multiple releases per week.

SaaS · M&A

Two acquisitions, both sides of the table

Ran technical due diligence on MagicWrighter for SWIVEL's acquisition, and represented engineering during Battery Ventures' acquisition of Chargify — then led the integration planning.

Cybersecurity

Four brands, one product org

Unified engineering teams from the Jungle Disk, LiveVault, KeepItSafe and OffSiteDataSync acquisitions into a single product organisation at CyberFortress.

Cloud Infrastructure

OpenStack at Rackspace scale

Led product for Cloud Identity (Keystone) and Key Management, helped launch Barbican as an official OpenStack project, and shipped Repose as an open developer toolkit.

Regulated Cloud

HIPAA-compliant infrastructure

Architected enterprise microservice and multi-cloud AWS solutions at ClearDATA, and carried core products through SOC 2, HITRUST and other major healthcare audits.

Portrait of Nathan Anderson

About

I've seen this movie before — in 1998, 2008 and 2018.

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

I started as the sole employee of a small ISP, scaling it from 100 to 3,000 customers in eighteen months. I spent thirteen years at Rackspace as it became a cloud company. I’ve led engineering at ClearDATA building HIPAA-compliant infrastructure, run global DevOps and compliance at Chargify through its acquisition, unified four acquired brands at CyberFortress, and reported to the CEO at SWIVEL through a reorganisation and an exit.

That range matters because your problem is rarely purely technical. It’s usually a technical problem wearing an organisational costume — and pattern recognition is the thing you can’t hire junior.

Outside client work I’m CTO of Alenio Health (Tú TeleDoc), a telemedicine venture serving Mexico and Latin America. I sit on the board of Tech Bloc and the Leadership San Antonio Alumni Association, and I mentor engineers, engineering leaders and founders at local universities.

Core competencies

  • Technology Strategy & Vision
  • Engineering Leadership
  • Cloud Architecture (AWS, Azure, GCP)
  • DevOps & CI/CD
  • Cybersecurity & Compliance
  • Technical Due Diligence
  • Digital Transformation
  • Team Building & Mentoring
  • Product Development

Experience

Career history

2025 - Present

Chief Technology Officer & Chief Product Officer

Alenio Health

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
April 2024 - Present

Fractional CTO

Nathan Anderson Consulting

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
February 2023 - April 2024

Vice President of Software Engineering

SWIVEL

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
February 2022 - February 2023

Chief Technology Officer

CyberFortress

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
July 2021 - February 2022

Vice President of DevOps and Engineering

Chargify (now Maxio)

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
Show 8 earlier roles
January 2019 - July 2021

Director of Engineering and DevOps

Chargify (now Maxio)

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
December 2015 - January 2019

Director of Engineering

ClearDATA

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
September 2013 - December 2015

Director of Product Management

Rackspace

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
June 2010 - September 2013

Senior Product Manager

Rackspace

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
June 2002 - June 2010

Software Development Manager

Rackspace

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
December 2000 - June 2002

Software Developer

Rackspace

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
1998 - December 2000

System Integrator

IPI GrammTech

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
1996 - 1998

System Administrator and Tech Support

InterSAT Internet

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

Writing

Notes from the trenches

Alamo Angels Founders Dinner

Alamo Angels Founders Dinner

Last night was one of those “refill the tank” kind of evenings. I had the chance to celebrate the ProsperOps team on their recent …

Alamo Angels Founders Dinner

Alamo Angels Founders Dinner

Dr. Jeremy Roberts and I spent a great evening with the Alamo Angels and a room full of founders building some interesting things …

Capital Factory - First Look

Capital Factory - First Look

It’s always great to get the word out about Tú TeleDoc and meet a bunch of great entrepreneurs, mentors, and funders. …

Let's talk

Tell me what's slowing your team down

A 30-minute call, no pitch. Bring the problem as you currently understand it — even if that's just "delivery feels slow and I can't tell why." If I'm not the right person, I'll tell you and point you somewhere better.