Why OtterBear Exists
Organizational clarity is rarely the recognized problem. Leaders don't say, "We need more clarity." They say execution feels harder than it should. They say things are moving too slowly. They say they're unclear about what matters most.
OtterBear exists because these issues aren't strategy or capability or talent problems. They're clarity problems. And when clarity breaks down — in how priorities cascade, how decisions get made, or how work flows between teams — even the best strategies and strongest teams lose momentum.
Who OtterBear Serves
OtterBear works with two groups: C-suite leaders and Boards navigating company transitions, and Directors and VPs tasked with making clarity real across their teams.
Usually OtterBear is brought in for transitions and pathfinding that include reorgs, growth, leadership changes, M&A, succession, and scaling challenges — especially when execution has outgrown structure.
Companies typically have 15 to 5,000 employees and are navigating the complexity that comes with growth, change, or sustained operations at scale.
What Makes OtterBear Different
Most consulting firms sell process. OtterBear sells pattern recognition. After working across dozens of companies — from rapid-growth startups to established mid-market businesses — the recurring friction points become visible: where ambiguity typically emerges first, what fixes actually stick, and how to build systems that survive growth and change.
The work isn't about implementing standardized frameworks. It's about understanding your specific context, identifying where breakdowns are happening, and building the structure and rhythms that work for how your company actually operates. No two engagements look identical because no two organizations are identical.
Who Founded OtterBear
OtterBear was founded by Mark Schindler, who has spent over 20 years in coaching, entrepreneurship, and leading go-to-market, product, and operations teams in high-growth companies.
Mark spent six years at Fountain, a workforce management platform, where he moved from product management into leadership roles spanning marketplace operations, sales strategy, and eventually serving as Chief of Staff. Before that, he led operations teams at OrderUp, a food delivery company acquired by Grubhub, building systems and teams through rapid scaling.
Throughout his career, especially after starting OtterBear and coaching dozens of executives, Mark saw the same pattern: talented teams slowing down not because of bad strategy or lack of capability, but because clarity had broken down. Priorities weren't cascading. Ownership was ambiguous. Decisions stalled in coordination loops. OtterBear exists to help companies identify and resolve these clarity gaps before they compound.
In 2025, Mark also founded The Second Circle Institute to address a related problem: Directors and VPs who are expected to lead strategically but often lack the judgment, influence, and clarity skills needed to operate effectively at that level. 2CI provides the leadership development that most organizations don't offer to the layer between frontline managers and the C-suite.
The Second Circle Institute is a leadership accelerator and professional network for Directors and VPs making the transition to executive leadership. 2CI serves the first and second lieutenants of the C-suite — helping them develop the judgment, influence, and strategic thinking needed to lead effectively in ambiguous, high-stakes environments.
While OtterBear focuses on organizational clarity at the company level, 2CI focuses on leadership development at the individual and cohort level. Many OtterBear clients send their Directors and VPs to 2CI as part of building leadership capability alongside organizational clarity. Learn more atthe2ci.com.
The Second Circle Institute
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Most clients start with the Organizational Clarity Scorecard or schedule a conversation to discuss their specific situation.