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Trish K

Fractional General Counsel | Strategic Regulatory Advisor for Mission-Driven Organizations

About Me

I am a U.S.-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 At Progression Strategies, LLC, I believe that complex or outdated regulations should never be a roadblock to impact.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.

Jurisdiction

United States

Notable Employer

  • SVP of Legal and Policy at HopSkipDrive

Experience

Seniority LevelExecutive
Years of Experience10-15 years
Current StatusActive
FounderProgression Strategies, LLC
2025 - Present

At Progression Strategies, I offer three primary services: 1. Fractional General Counsel What It Is: Senior-level legal leadership on a flexible, part-time basis. What I Deliver: I serve as an embedded, strategic partner to advise on regulatory issues, manage commercial/vendor contracts, guide external counsel, and design internal legal systems to support your growth. Ideal For: Startups or non-profits needing executive-level legal oversight without the permanent headcount. 2. Legal & Policy Strategic Advising What It Is: Crafting comprehensive plans to shape the regulatory landscape. What I Deliver: A clear, actionable roadmap for policy change or a detailed report on the regulatory landscape tailored to your goals. Ideal For: Organizations seeking to influence major institutional systems or remove barriers to expansion. 3. General Legal Advising & Compliance What It Is: Fast, expert counsel for specific legal or compliance questions. What I Deliver: Expert guidance on worker classification, government contract negotiations, and short-term business legal needs. Ideal For: Quick, reliable help without a long-term commitment.

SVP of Legal and PolicyNotableHopSkipDrive
2019 - 2025

Senior executive and legal counsel for a high-growth K-12 student mobility solution. Regulatory Innovation & Legislative Strategy Pioneered a new regulatory category for youth rideshare services, navigating complex intersections of technology, student transportation, and employment law to drive expansion from 2 to 15+ states. Drafted and advocated for high-stakes legislation, including relief efforts regarding CA AB5 to protect caregiver opportunities and expanding student mobility access to 15+ states. Served as the primary liaison to government agencies, securing licenses and permits in 15+ states that unlocked partnerships with hundreds of school districts and foster care agencies. Orchestrated participation in formal rulemaking and oversaw contract lobbying efforts to proactively shape the policy landscape for the student mobility sector. Legal Operations & Risk Management Built the legal, regulatory, and public affairs functions from the ground up, scaling to a diverse team of 24 professionals. Revitalized core legal infrastructure, including full-scale revisions of Privacy Policies, Terms of Use, and cross-departmental contract review processes. Managed a comprehensive insurance and risk portfolio, including SaaS and public agency agreements, while serving as a key driver of Crisis Response and Safety initiatives. Directed all external counsel work, ensuring high-level strategic alignment and cost-effective legal support. Mission & Social Impact Removed mobility barriers for youth experiencing homelessness, those in foster care, and students with special needs through targeted policy initiatives. Designed and launched "HopSkipImpact," a philanthropic program ensuring equitable mobility access for all families.

Director of Policy & Legal InitiativesColorado Charter School Institute
2016 - 2019

State-level regulatory lead building legal and compliance infrastructure for a statewide charter school authorizer. Institutional Infrastructure & Governance Architected and launched the inaugural legal and policy function for the agency, establishing foundational frameworks where none previously existed. Served as a core leadership team member, driving organization-wide strategic planning and leading annual organizational evaluations to ensure state standards were met. Developed and managed comprehensive Board policies and staff procedures to ensure transparent, consistent governance across the agency. Regulatory Design & Compliance Monitoring Designed and implemented sophisticated compliance monitoring systems to evaluate the organizational performance of member schools against education and organizational best practices. Drafted and negotiated complex charter school contracts and amendments, overseeing their implementation to ensure rigorous legal and operational alignment. Established objective operational performance indicators for member schools, translating state law into actionable metrics for institutional success. Strategic Communications & Policy Advocacy Created a high-impact communication system to translate legislative and regulatory changes into practical FAQs and resources, supporting compliance efforts for school leaders. Monitored and analyzed state and national legal developments, developing and executing organizational strategies to respond to shifting policy landscapes. Served as a key liaison for interpreting complex regulations, helping to influence institutional systems to improve access and outcomes for students.

Senior Legal AnalystColorado League of Charter Schools
2015 - 2016

Lead policy analyst and researcher focused on legislative advocacy and school sustainability. Thought Leadership & Policy Research Authored and published influential white papers on high-stakes policy issues, providing the evidence base for statewide legislative advocacy. Conducted deep-dive analysis into Medicaid funding for school health programs, identifying pathways to increase resource access for underserved student populations. Spearheaded research on facility accessibility, addressing the critical gap in affordable school infrastructure for charter organizations. Legislative & Risk Advocacy Evaluated school safety legislation to provide member schools with actionable insights on compliance and implementation strategies. Produced comprehensive guidance on governmental immunity, helping school leaders understand and navigate complex liability and risk management landscapes. Translated complex legal concepts into accessible resources, enabling mission-driven leaders to engage effectively with state-level policy shifts.

Associate AttorneyRichard J. Nakon & Associates
2013 - 2015

Lead associate for a high-volume general practice specializing in real estate and civil litigation. High-Volume Transactional Management Managed and processed a high volume of residential real estate transactions, overseeing the entire lifecycle from contract to closing with meticulous attention to detail and timeline management. Supported in drafting and negotiating commercial real estate agreements, ensuring client interests were protected in complex property acquisitions and leases. Acted as a primary point of contact for clients, navigating high-pressure deadlines while maintaining a focus on clear communication and risk mitigation. Civil Litigation & Dispute Resolution Advised on landlord-tenant disputes, providing strategic counsel to resolve conflicts efficiently and, where possible, avoid protracted litigation. Managed uncontested divorce proceedings, guiding clients through sensitive legal processes with empathy, professionalism, and administrative precision. Developed a reputation for being a "roll-up-your-sleeves" attorney, balancing a diverse caseload that required rapid issue-spotting and creative problem-solving across multiple areas of law.

Legal InternColorado League of Charter Schools
2011 - 2013

Strategic legal and policy support focused on legislative advocacy and school-level operational counseling. Legislative Advocacy & Policy Impact Instrumental in the passage of a state capital construction bill, producing legislator-specific cost-benefit analyses that successfully increased state funding for charter school facilities. Developed a "Legislative Toolkit" used by state lawmakers to navigate complex charter-related issues and improve the quality of education policy. Architected a strategic community advocacy initiative, engaging public opinion leaders and increasing parent involvement in charter school policy at the local level. Legal Counseling & Compliance Provided expert support to charter schools on HR and employment law issues, delivering advisory bulletins, seminars, and personalized guidance on employment policies. Advised charter school leaders on nonprofit and governmental entity status, including navigating the 2012 mandate for nonprofit incorporation and its associated tax implications. Published author in Charter Focus magazine, providing statewide guidance on Financial Transparency Act compliance.

Founding Intern and Program ManagerUniversity Prep Charter School
2011 - 2011

Early-stage operational lead for the launch of a K-5 charter school in Denver. Startup Operations & Community Engagement Supported the foundational "start-up" phase of a K-5 school, gaining firsthand insight into the legal and operational complexities of establishing a new educational institution. Spearheaded community outreach initiatives, specifically engaging Spanish-speaking community members to ensure inclusive access and enrollment. Researched and secured critical community resources, bridging the gap between school families and essential health and social services. Program Leadership & Strategy Coordinated comprehensive after-school programming and led the planning for annual college visits, fostering a culture of high expectations and long-term student success. Completed an intensive summer teacher institute, deepening my understanding of the pedagogical and staffing challenges inherent in high-growth mission-driven environments. Acted as a versatile problem-solver during the critical launch year, managing everything from logistics to family relations to ensure a successful school opening.

Education

Doctorate of LLM - Child and Family Law, Focus on Education Law & PolicyLoyola University Chicago
2015 - 2016
Doctorate of J.D.University of Denver
2010 - 2013
Degree of BA - Spanish & Portuguese Languages and LiteratureUniversity of Colorado - Boulder
2009 - 2010

Certification

Total Certifications1

License to Practice Law

Colorado Supreme Court

Skills

Core skills0
Languages1

Languages

English