Steve Raines

Work history

Recovering entrepreneur, with a specialization in modernizing teams and code. My work is highly focused on how to best improve quality and velocity, coordinate a global team, stay compliant, and use AI to accelerate everything we do.

Full history on LinkedIn

How I work

How I think
Not every idea is an opportunity, so I focus on the ones that generate value. I’m always looking for the smallest thing that moves the needle. Building for what users “want” is building one-off solutions. Ask why, over and over. Users should deliver problems, you should deliver solutions.
How I lead
Real leaders are always out front, and never ask anyone to do something they wouldn’t do themselves. I believe deeply we should always “Fix the problem, not the blame.”
How I build
The inviolate law of building software is to get things in front of users. If you think it’s ready to ship, you’ve waited too long. Whatever you deliver, someone is going to hate it. You just have to embrace that.

Experience

  1. RouteGenie

    Since 2026

    Head of Technology

    Focusing on scalability, security and compliance, I lead a globally distributed engineering team that builds the premier scheduling, billing, routing and dispatch software for the medical transportation industry.

    A few places where AI has earned its keep on the team so far:

    • SOC 2 evidence gathering, down from several days to about 20 minutes
    • A bug-fix loop that writes a failing test, builds the fix, and records a visual check for a person to review
    • Live prototypes during requirements sessions, built on a design system with accessibility built in
    • Turning the questions people ask in Slack into improvements to the product
    • A “work brain” that keeps track of the day and drafts weekly one-on-one notes

  2. CaseGlide

    2023–2026

    Chief Technology Officer

    Led an in-place modernization of a legal-tech SaaS platform from .NET 4.5 to a service-based .NET Core architecture, with 50% faster load times. Kept delivery on schedule with a 40% smaller team, pre-AI tooling, by refocusing senior engineers on high-value work and through pair programming and daily knowledge sharing. Cut AWS costs by 30% in the first 6 months, and integrated LLM tools that let 23% of clients eliminate duplicate work.

  3. 19 Ideas

    2021–2023

    Software Development Director

    Executive team member, overseeing all application development. Led a distributed team of 15 across analysis, engineering and QA, implementing a $3M+ government contract for process management software, including integration with New York State’s financial systems.

  4. Pointman

    2007–2020

    Co-founder, COO (former CTO)

    Co-founded and grew the field service SaaS platform to 50+ people and $8M+ ARR, with 98% month-over-month retention; acquired, 2020. Shipped mobile workforce software before the iPhone, and built a payments platform that securely processed over $1B.

  5. Algonquin Studios

    1998–2016

    Co-founder, CEO (former COO)

    Ran a $7M+ software consultancy delivering 75+ projects a year at 98% client satisfaction. Specialized in HIPAA-compliant healthcare work, including a secure system for sharing patient data across New York State.

Community and education

  • Entrepreneur in Residence, Launch NY (Since 2021)
  • Co-founder and Managing Director, VCAMP (2015–2016)
    A health IT startup accelerator.
  • Technology Mentor, 43North (2015–2017)
  • Board Member, Infotech Niagara (2014–2015)
  • Co-founder, Algonquin Sports for Kids (2007)
  • B.A. in English, University at Buffalo
  • Center for Entrepreneurial Leadership, University at Buffalo