
Trish Krajniak
Helping mission-driven organizations navigate complex regulations
About
I am a Colorado-based attorney with over 12 years of experience helping mission-driven organizations navigate the intersection of law and policy. At Progression Strategies, LLC, I believe that complex or outdated regulations should never be a roadblock to impact.
What I bring to organizations is a unique dual perspective: I have worked both as a government regulator and as a leader in a high-growth technology startup. This allows me to build bridges between innovation and compliance, transforming legal hurdles into strategic advantages for your mission.
My robust in-house experience also means that I have experience reviewing and negotiating a variety of different contracts (SaaS, vendor, contractor, and government contracts), managing external counsel, advising on insurance coverage, strategic legal and policy planning, and more.
I am a hands-on problem-solver who is ready to roll up my sleeves and plug directly into your team to drive real change.
Expertise: Education (K-12), Transportation, Telecom, Nonprofits, and more
Regulatory Innovation: Deep experience creating new regulatory categories and conducting in-depth analyses to ensure companies are benefitting from the most advantageous applicable regulations.
Global & Local Reach: Based in Colorado (United States) but capable of supporting organizations navigating multi-jurisdictional challenges.
Specific Services: My consultancy, Progression Strategies, LLC, offers three main services, enabled by my prior public and private sector experiences: 1. Legal & Policy Strategic Advising: Crafting comprehensive policy plans designed to help you achieve the organization's goals. 2. Fractional General Counsel: Providing the senior-level legal guidance an organization needs, on a flexible basis. 3. General Legal Advising: Offering expert counsel on a wide range of issues based on my in-house and public sector experience.
Practice areas
- Administrative Law
- General Corporate
- Commercial Contracts
- Education Law
Featured clients
- HopSkipDrive
- Colorado Charter School Institute
Services
Fractional General Counsel
Ongoing, high-level support without the overhead of a full-time hire.
Strategic Legal and Policy Advising
Project-based solution to target specific compliance or policy challenges.
Hourly Advising
Flexible, as-needed legal or policy guidance.
Experience

Senior Vice President of Legal & Policy
HopSkipDrive
Jul 2019 – Sep 2025
Director of Legal & Policy
Colorado Charter School Institute
Jul 2016 – Feb 2019

Senior Legal Analyst
Colorado League of Charter Schools
Sep 2015 – May 2016
LLM - Child and Family Law
Loyola University - Chicago
2016
J.D.
University of Denver
2013