AboutMark Schindler is a leadership advisor who helps organizations reduce Clarity Debt as they grow.
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 decisions are taking too long. They say they're not sure what matters most right now.
OtterBear exists because these aren't strategy problems or talent problems. They're clarity problems. And when clarity breaks down — in how priorities cascade, how decisions get made, or how work moves between teams — even strong teams with sound strategies lose momentum.
OtterBear works primarily with CEOs, COOs, founders, and Boards at companies navigating growth, change, or growing complexity — particularly when execution has outgrown the structure around it.
Engagements most often involve transitions: reorgs, rapid scaling, leadership changes, post-acquisition integration, or succession. Companies typically have between 15 and 5,000 employees and are navigating the kind of complexity that makes the leadership operating model feel like it's falling behind the business.
Directors and VPs are also a focus — both through direct coaching and advisory work, and through The Second Circle Institute.
Who OtterBear Serves
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 structure that survives 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.
The pattern showed up everywhere. Talented teams slowing down — not because of bad strategy or lack of capability, but because clarity had broken down at the leadership level. Priorities weren't cascading. Ownership was ambiguous. Decisions were stalling in coordination loops. Nobody had named it yet.
Mark Schindler is a leadership advisor who helps organizations reduce Clarity Debt as they grow. He spent over 20 years in coaching, entrepreneurship, and operational leadership — including six years at Fountain as Chief of Staff, and earlier building operations at OrderUp through its acquisition by Grubhub. Across dozens of engagements since, the same pattern kept appearing. OtterBear exists to name it, diagnose it, and fix it.
Most advisors sell process. Mark sells pattern recognition — the ability to see where clarity is breaking down before the organization can name it themselves.
Who Founded OtterBear
The Second Circle Institute
In 2025, Mark also founded The Second Circle Institute to address a related problem: Directors and VPs who carry significant responsibility but often lack the judgment, influence, and strategic clarity needed to operate effectively at that level.
2CI is a leadership accelerator and professional network for senior non-executive leaders — the first and second lieutenants of the C-suite. It provides the development that most organizations don't offer to the layer between frontline managers and the executive team.
Many OtterBear clients send their Directors and VPs to 2CI as part of building leadership capability alongside organizational clarity.
Learn more at the2ci.com.
If this sounds like the right kind of help, it's worth a conversation.
No preparation needed — just a direct discussion about what's going on and whether this kind of work makes sense.