In this episode of Software Without Borders, Andy and Scott sit down with Kristina Crane, transformational executive, fractional COO/CSO, and CEO of The Canyons Group, to unpack what it really takes to lead organizations through AI-driven change. Kristina draws on 25+ years across SaaS, government tech, and operational transformation to explain how companies can embrace AI without losing their people, culture, or strategic focus. From building a “culture of curiosity” to using proven software-industry frameworks for prioritization, Kristina brings a grounded, practical perspective on how leaders can move fast and smart.
Guest Introduction:
Kristina Crane is a transformational executive and fractional COO/CSO with deep expertise in AI adoption, organizational change, and strategic operations. As CEO of The Canyons Group, she helps government agencies, enterprises, and growth-stage companies navigate complex transitions with a framework centered on “Navigate to Elevate.” Kristina spent 12+ years at STC Health leading a major shift from a dev-shop model to a scaled SaaS organization, driving 10x revenue and 60% efficiency gains through AI.
Key Takeaways:
• AI transformation is a people problem first—tech only works when teams understand the “why” and feel empowered. episode-37
• Companies must balance curiosity with prioritization to avoid shiny-object chaos.
• The software industry provides proven frameworks (like RICE) that non-tech organizations can use to evaluate AI opportunities.
• Old-school executive teams need a business-first, tech-translated approach to adopt AI successfully.
• Strategic planning cycles must speed up—leaders should revisit their business model, ICP, and value proposition every 12–36 months.
• Consultants accelerate outcomes not because of frameworks, but because of pattern recognition and objective accountability.
Chapter Markers:
0:00 Intro
1:07 Welcome to Software Without Borders
1:12 Introducing Guest — Kristina Crane
1:56 Kristina’s Background in Strategy, SaaS & GovTech
3:41 Teaching Roots → Consulting → SaaS Incubation
5:58 Transition to STC Health & Leading SaaS Transformation
6:34 Difference Between Kale Crane & The Canyons Group
8:08 AI FOMO, Human Intelligence & Organizational Change
9:03 Navigating Noise & Extremes Around AI
10:26 What AI Forces Every Organization to Learn
12:30 How Old-School Exec Teams Can Embrace AI
14:14 Culture of Curiosity & Empowering Teams
15:34 Guardrails, Governance & Safe Experimentation
16:57 When to Bring in Technologists
17:12 Prioritization Frameworks (RICE & ICE)
18:54 Governance Policies & Early-Stage Experimentation
19:29 Curiosity Champion Groups & Brown-Bag Cycles
22:22 Training Teams to Think Like Product Organizations
23:19 Overcoming Fear & Starting Small
23:46 Strategy vs. Operations — Big Picture Impacts
24:58 Business Model Iteration in the AI Era
26:51 The SaaS Business Model Shift as an Analogy
28:12 Professional Services & White-Collar AI Disruption
29:37 Innovating Without Breaking the Core Business
30:01 Leading Large-Scale Change Inside Mature Organizations
32:21 Why Consultants Matter in AI Transformation
33:15 Seeing Blind Spots & Reading Culture
34:10 Accountability, Execution & “Skinned Knees”
35:13 The Hardest Transformation Leaders Will Face
End Closing Thoughts
Keywords:
Software Without Borders, Andy Hilliard, Scott Pollov, Kristina Crane, The Canyons Group, AI transformation, organizational change, SaaS transformation, leadership, culture of curiosity, AI adoption, operational strategy, RICE prioritization, business model evolution, enterprise AI, government tech
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