Joining us this episode is Jeff Walker, Senior Vice President of Corporate Strategy and M&A at BraunAbility — a company that builds wheelchair-accessible vehicles, founded fifty-five years ago in an Indiana garage by Ralph Braun and now owned by the Swedish patient-capital investor Investor AB through its Patricia Industries arm. Educated at Yale and Dartmouth's Tuck School of Business, where he studied under the legendary endowment investor David Swensen, Jeff sees strategy through three lenses: the historian's pattern recognition, the economist's sense of cost versus value, and a parent's. In this conversation, we explore a deceptively simple question every strategy leader should be able to answer: what is the strategy office actually for, and how do you know it's adding value rather than quietly taxing the business it serves?

Things we will cover:

- Why "the center" is best understood not as a group of smarter people who second-guess the business, but as a decision boundary — the place where enterprise-wide choices naturally belong
The two tests for what truly belongs at the center: scale (cross-business leverage) and duration (the length of the strategic bet)
- The "two seams" framework — a stated priority with no resources behind it, and a shadow project with no bets behind it
Jeff's sharpest warning: never mistake curiosity for value-creating results, and the passive-investing philosophy underneath it
- Why every question you pose to the business is a tax that had better be driving alpha before you ask it
- His make-versus-buy default for strategy work, and why he runs the center as a team of one
The strategist as a parent — someone who sets things up, teaches, and gets out of the way, rather than the invisible hand behind the curtain

From David Swensen's table to the M&A seat, Jeff offers an unusually honest set of tools for pressure-testing your own role. Before you ask the business your next recurring question, can you name the choice it might change — and why that change is worth the organization's time? For any strategy leader, it's a bracing invitation to earn your place at the center.

Additional Resources:

LinkedIn: https://www.linkedin.com/in/jeffreycwalker/
BraunAbility: https://www.braunability.com
Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Thank you to our guest Jeff Walker for such a thoughtful and honest conversation.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Joining us this episode is Carrie Hanna, Chief Strategy Officer at Gunster — a century-old firm that is one of Florida's largest, with around 340 attorneys across offices statewide. A legal-marketing professional by background with more than thirty years in the field, Carrie has spent the majority of her career at Gunster, first as a consultant and then stepping into the CSO role when the firm launched its strategic plan in 2007. She brings a rare vantage point on a hard problem: how you build one cohesive strategy inside a professional-services firm full of independent, self-directed practitioners. In this conversation, we explore how a law firm — an industry built to be siloed — created a single North Star, and what any strategy leader can borrow from it.

Things covered:

- Why law firms are structurally siloed, and how Gunster built a collaboration-first, people-first culture instead
- The four pillars of the firm's five-year vision — the "Gunster Way," market presence, client relationships, and technology — and how to define a pillar broad enough to pivot but specific enough to direct
- Where a legal CSO looks for inspiration: borrowing the corporate operating model and lessons from the Big Four
- How to get independent practitioners to care about the firm, not just their own P&L — through story, data, and the client voice
- The difference between an answer and a decision, and why who is in the room determines which one you get
- Building a leadership pipeline through a bespoke "Future Leaders" programme, and running an annual planning "report card"
- Why Gunster aims to be a "bronze medalist" in AI — a deliberate near-follower stance in a fast-moving field

From forcing the hard conversations to reinvesting in future leadership, Carrie offers one of the most practical, grounded views you'll hear on turning a fragmented professional-services organisation into a cohesive whole. For any strategy leader building an office from scratch, her advice on ownership, accountability, and treating the plan as a living process is worth the listen alone.

Additional Resources:

LinkedIn: https://www.linkedin.com/in/carrie-hanna/
Gunster: https://www.gunster.com
Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Thank you to our guest Carrie Hanna for such a generous and practical conversation.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Joining us this episode is Claudio Finol, Chief Innovation and Strategy Officer at Fyffes — one of the world's leading fresh produce companies, owned by Japan's Sumitomo Corporation. An engineer by training with an MBA from Alliance Manchester Business School, where he also teaches, Claudio has led innovation and strategy across Chiquita, Danone, FrieslandCampina, and McBride. He brings a rare cross-industry lens to the discipline — part academic, part practitioner — and a conviction that strategy should sit far closer to execution than most strategy offices allow. In this conversation, we explore why the pursuit of stability, the very thing most strategy functions are built to deliver, may be the hidden weakness that brings an organisation down.
Things we will cover:

The Icarus principle applied to strategy, and why over-reliance on stability is more dangerous than over-reliance on strength
Why adaptability is less about managing change and more about constantly challenging the assumptions beneath every plan
The tension between efficiency and resilience, and why real resilience demands a degree of redundancy by design
The "velocity of risk" — not just how big a threat is, but how fast it can surface, from steady regulation to a blind side like DeepSeek
How to reframe risk as opportunity, and why the risk function and strategy function need to work in concert
Reconciling a fast-moving external environment with long-horizon ownership expectations
The Chief Strategy Officer as "chief reminder officer" — keeper of a living, adaptive process rather than the executor of a fixed plan

From the Icarus principle to the chief reminder officer, Claudio draws on experience across some of the world's best-known consumer and industrial brands to make a grounded case that the real work of strategy is never finished — because the assumptions underneath every plan are always shifting.
Episode Timeline:

Additional Resources:

LinkedIn: https://www.linkedin.com/in/claudiofinol/
Fyffes: https://www.fyffes.com
Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Thank you to our guest Claudio Finol for such a thoughtful and genuinely practical conversation.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Joanne Sheppard is a strategic advisor to the Holzbrinck Group — the German family holding company behind Macmillan Publishers, Springer Nature, and Die Zeit — and a board member across several of its owned and invested companies. Her career spans publishing, M&A, and corporate strategy, and she brings an unusually wide lens to her work: graduate study in English literature, executive education in AI and innovation at MIT, positive psychology from Penn, and board governance through INSEAD.

In this conversation, we explore why AI adoption stalls inside large organisations — and why the answer has far less to do with technology than most leaders assume.

Things we will cover:

• Why AI adoption is fundamentally a change management problem, not a technology problem
• How to build the psychological safety that makes experimentation and upskilling possible
• What IKEA and JP Morgan can teach us about bringing employees along on the journey
• How to think about reinvesting the productivity AI frees up — and why that decision deserves a quarterly board conversation
• The architects, bridgers, and catalysts framework for understanding the role of leadership in driving adoption

From employee resistance to board-level strategy, Joanne draws on real experience inside a complex, decentralised organisation to offer one of the most grounded and human-centred perspectives on AI adoption you'll hear.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Today’s guest is Adam Zalisk, Chief Strategy Officer at Amplify — a pioneer in K–12 education since 2000. Today, Amplify serves more than 10 million students across all 50 U.S. states, delivering next-generation curriculum and formative assessment in ELA, math, and science.

In this conversation, Adam reflects on what changes when strategy becomes a formal role inside a growing organization. Rather than treating strategy as a static plan, he frames it as a set of clear commitments tied to an explicit end state — and explains why ambiguity around those commitments is often what causes companies to struggle as they scale. He also introduces a practical framework for understanding why strategy offices emerge in the first place, helping leaders distinguish between different strategic needs and translate strategic thinking into real organizational traction.

Things we’ll cover:

• How Adam defines strategy in growth-stage companies
• The four distinct reasons organizations create a strategy office
• What leaders are actually looking for when they say, “we need strategy”
• How a strategy office avoids becoming an internal order-taker
• Where strategy functions most often lose — or earn — credibility

This episode is a practical guide for CSOs navigating growth, ambiguity, and rising organizational complexity. If you’re wrestling with focus, alignment, or execution as your organization scales, this conversation will sharpen how you think about the role — and the impact — of strategy.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Neil Hoyne joins Kaihan Krippendorff to unpack why most strategy failures aren’t caused by a lack of data — they’re caused by organizations asking the wrong questions, setting the wrong standards, and rewarding the wrong behaviors.

Neil is Google’s Chief Strategist and the bestselling author of Converted. In this conversation, he shares how he thinks about strategy as an incremental discipline: keeping the business alive today while moving it into a stronger position tomorrow.

They explore how leaders unintentionally turn metrics into theatre, why “more measurement” often becomes a coping mechanism, and how to set decision standards that match the speed of your competitive environment. The conversation also examines where AI can amplify strategic confusion, and how CSOs can keep strategy anchored in what customers actually value.

Things we’ll cover:
How Neil defines strategy as survival + positioning
Product-led vs customer-led models (and the role marketing plays in each)
Customer lifetime value and what it changes in enterprise strategy
Why common metrics aren’t comparable (even when they share the same name)
The “manipulation test” to reveal weak KPIs
How leaders override data — and how to design better decision standards
Why AI adoption fails when strategy is unclear

Learn more about Outthinker’s community of chief strategy officers - https://outthinker.com/
Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Today’s guest is Adam Zalisk, Chief Strategy Officer at Amplify — a pioneer in K–12 education since 2000. Today, Amplify serves more than 10 million students across all 50 U.S. states, delivering next-generation curriculum and formative assessment in ELA, math, and science.

In this conversation, Adam reflects on what changes when strategy becomes a formal role inside a growing organization. Rather than treating strategy as a static plan, he frames it as a set of clear commitments tied to an explicit end state — and explains why ambiguity around those commitments is often what causes companies to struggle as they scale. He also introduces a practical framework for understanding why strategy offices emerge in the first place, helping leaders distinguish between different strategic needs and translate strategic thinking into real organizational traction.

Things we’ll cover:

• How Adam defines strategy in growth-stage companies
• The four distinct reasons organizations create a strategy office
• What leaders are actually looking for when they say, “we need strategy”
• How a strategy office avoids becoming an internal order-taker
• Where strategy functions most often lose — or earn — credibility

This episode is a practical guide for CSOs navigating growth, ambiguity, and rising organizational complexity. If you’re wrestling with focus, alignment, or execution as your organization scales, this conversation will sharpen how you think about the role — and the impact — of strategy.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks

Today’s guest is Michael Drexler, Chief Strategy Officer at Brightstar Capital Partners, a private equity firm that invests in closely held, middle-market businesses and helps them scale into professional, process-driven organizations.

Michael’s career spans leadership roles across investment banking, global strategy, and private equity—from Barclays to the World Economic Forum, and Brightstar Capital Partners—giving him a rare perspective on how strategy functions evolve as companies mature from founder-led to institutional scale.

In this conversation, we unpack lessons from Michael’s career leading strategy functions and explore how the head of strategy role transforms along a company’s growth journey.

Things we will cover:

• How strategy evolves from a “chief of staff” role in founder-led companies to a full-fledged internal consulting function
• The mindset shift from advising a single CEO to influencing a broader leadership team
• How to build and sustain an effective strategy team—including Michael’s “2-to-4-year rotation” and “no bad news for two weeks” rules
• Why private equity firms view internal strategy functions differently—and how to reposition your team in a PE environment
• Michael’s four-step framework for prioritizing projects that’s “never failed him once”

From developing consulting-style skillsets inside corporations to balancing neutrality among competing executives, Michael brings clarity and practicality to what it means to be an effective CSO.

• Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
• Follow us on LinkedIn - https://www.linkedin.com/company/outthinker-networks