The Chief Strategy Officer AI Summit
Join your fellow strategy leaders for our upcoming Outthinker Summit, an exclusive live event designed specifically for our network members. This intimate gathering brings together Chief Strategy Officers, Chief Transformation Officers, and ELT Strategy executives from Fortune 1000 and $B+ public & private companies for a day of peer-to-peer collaboration and strategic insight exchange.
You'll connect with the collective genius of our network through dynamic sessions, rapid challenge forums, and curated networking opportunities—all focused on the critical issues shaping your role today. This isn't a typical conference; it's a transformational experience where you'll engage directly with peers facing similar challenges. You'll leave with new connections and practical, actionable solutions.
A big thank you to our host and longtime Outthinker member – TIAA, and to our partner Disruptive Edge making the summit possible.
Agenda & Timings
May 27 – Group Dinner at Serafina (*241 Madison Avenue, New York, NY)
6:00–9:00 PM — Informal dinner at Serafina Italian restaurant in their private dining area
* Note specific address, as there are multiple Manhattan Serafina locations
May 28 – Outthinker Summit hosted by TIAA (730 3rd Avenue, New York, NY)
8:30 AM — Registration, breakfast, and networking
9:00 AM — Welcome and introductions
9:30 AM — The Synthetic Strategist (AI synthetic data and research)
10:45 AM — Networking + coffee break
11:15 AM — Architecting Strategic Partnerships (CSO peer-lead “How I did it” case)
12:15 PM — Networking lunch
1:15 PM — When the Cost of Cognition Collapses, What Happens to Your Moat?
2:00 PM — Challenge Forums
2:55 PM — Networking + coffee break
3:10 PM — How AI is Changing the Core Job of the CSO & Strategy Office
4:10 PM — Learning capture & close
4:30–5:30 PM — Networking reception
What to Expect
Summits are facilitated by Kaihan Krippendorff, Founder of Outthinker, Wharton Senior Fellow, podcast host, and top 20 ranked management thinker and business strategist by Global Gurus & Thinkers50.
The summit combines structured learning, peer exchange, and practical insight designed to accelerate your strategic impact.
You'll gain:
Cutting-edge applications of AI to strategy and decision-making
The latest tools and techniques to keep you at the cutting edge of strategy practice
Opportunities to contribute to your peers' toughest strategic questions and walk away with new connections and insights
Peer-to-peer guidance on your most urgent challenges through Rapid Round Challenge Forums
Speakers and Topics
The Synthetic Strategist
What if you could interview 1,000 of the people who matter most to your strategy? The hard-to-reach customers, executive decision makers, and new market segments that are nearly impossible to get in a room or survey — not next quarter, but in the next six minutes?
Peter Weinberg, co-founder of Evidenza and former head of LinkedIn’s B2B Institute, has built exactly that capability: a synthetic research platform that replaces slow, expensive traditional market research with AI-generated respondents that match real human decision-makers with startling accuracy. For Chief Strategy Officers, this rewrites the rules of how quickly and confidently you can validate strategic assumptions, test positioning, and size market opportunities. But Weinberg’s deeper argument is about competitive edge: in a world where AI can generate infinite answers, the strategists who win will be the ones who know how to ask the right questions.
About the Speaker
Peter Weinberg is a co-founder of Evidenza, synthetic research platform surveys AI-generated copies of customers to produce market research 100X faster than traditional approaches, with the same level of accuracy. Their focus is on quantitive research for hard-to-reach B2B populations. Prior to Evidenza, Peter worked at LinkedIn for over a decade, where I co-founded the Linkedin B2B Institute where he partnered with the world's leading experts and academics to research the fundamental principles of growth in B2B marketing. Outside of work, Peter is a profoundly unsuccessful science fiction novelist, father of two, and a devoted Nintendo player. He was born, raised, and will eventually die in New York City.
TIAA & Vanguard: How Two CSOs Created a New Category Through an Unlikely Partnership
Strategic partnerships are often described in hindsight as inevitable. In practice, they begin as improbable conversations between people who see something others don’t — and who have the conviction and relationships to turn that vision into reality.
Eric Goldstein, EVP & Chief Strategic Growth Officer at TIAA, will walk strategy peers through exactly how one such conversation — between two chief strategy officers who shared a mission-driven worldview — gave rise to the Vanguard Target Retirement Lifetime Income Trusts: the first product in Vanguard’s history to embed a third-party guaranteed income annuity inside its target-date fund structure.
Eric will share how mission alignment unlocked what competitive logic alone could not, how the vision was built and socialized into something both organizations could commit to, and what it took to bring a genuinely unprecedented product to market. He’ll also reflect on the broader strategic questions the experience surfaces: How do you build a case for something that has no precedent? How do you find the right partner when the logic isn’t purely competitive? And what does it mean for strategy officers to function not just as planners, but as architects of growth?
The session will be structured as a case walk-through followed by an open peer conversation, giving attendees the opportunity to draw parallels to their own partnership challenges, portfolio decisions, and growth mandates.
About the Speaker
Eric Goldstein is Chief Strategic Growth Officer at TIAA, the leading provider of retirement services for those in the academic, research, medical, and nonprofit fields, with over $1.4 trillion in assets under management. Previously serving as TIAA’s Chief Strategy Officer, Eric was the architect of a landmark partnership with Vanguard — resulting in the Vanguard Target Retirement Lifetime Income Trusts, the first product in Vanguard’s history to embed a third-party guaranteed income annuity inside its target-date fund structure. Before TIAA, Eric held senior roles in investment banking at JPMorgan and management consulting at McKinsey & Company, and earned his law degree from Yale Law School.
When the Cost of Cognition Collapses, What Happens to Your Moat?
Classical economics treats labor and capital as the two constrained inputs to any production function — the scarce ingredients that every firm must assemble and deploy. For a century, strategy has been built on top of that assumption: competitive advantage comes from acquiring hard-to-replicate labor — talent, expertise, institutional knowledge — and combining it with capital better than your rivals. The structural forces that shape an industry, the resources that make a firm defensible, the very concept of a moat — all of it presumes that cognitive work is costly, finite, and difficult to transfer.
What happens when that presumption breaks?
Jonathan Rosenfeld leads the Fundamental AI Group at MIT CSAIL, where computer scientists and economists work side by side on two questions most AI forecasters skip: What is physically possible? and What is economically viable? His foundational work on the laws of scaling — published in 2019, before the field had consensus — maps the real trajectory of AI capability against the real cost of running it. The trendlines suggest something that looks less like an efficiency gain and more like a phase transition. Task horizons are expanding 10x per model generation. Compute-per-watt is improving 100x per step. The marginal cost of a unit of cognitive work is collapsing toward the cost of the electricity it consumes.
If that's true, the structural sources of advantage need re-examination. When labor ceases to be scarce, what takes its place? Why did Microsoft — with GitHub, early OpenAI access, and every structural advantage — lose the coding-agent race to Cursor? What's defensible when headcount and capability decouple? And what should a Chief Strategy Officer be doing about it this quarter, not this decade?
Jonathan will lay out the economics, walk us through the physics underneath, and put a set of provocative claims on the table for the room to dissect. Bring your industry, your moat, and your skepticism.
About the speaker
Dr. Rosenfeld is Co-Founder and CTO at Cellular Intelligence. As an accomplished AI executive and entrepreneur with over 20 years of experience, he has directed large-scale efforts and teams, including hundreds of engineers, and has been at the forefront of research and strategy in areas such as AI, genomics, physics, and information theory. Recognized for driving industry-defining breakthroughs, particularly in the fundamental underpinnings of AI via scaling laws, his foundational work at MIT has significantly advanced the field. He holds five degrees: Ph.D. and MSc in CS from MIT, and a BA in Physics, a BSc in EE, and an MBA from the Technion. Dr. Rosenfeld was also the Valedictorian of the IDF's elite Psagot program.
The Strategy Officer’s Core Job—and How AI Is Changing It
The real work of a strategy officer is not analytical optimization—it is political and social. The true “job to be done” is to bring senior leaders to collectively align on, believe in, and commit to the right decisions, often in the face of uncertainty, competing interests, and imperfect information. In this session, David Duncan will explore how AI is beginning to reshape that core responsibility. Moving beyond tools and technologies, David will examine how AI is changing the way strategic conversations are framed, how scenarios are explored, how consequences—both intended and unintended—are surfaced, and how leaders come to buy into difficult choices. Drawing on real, cutting-edge applications across a range of businesses and situations, this session will show how AI is influencing not just strategic analysis, but the human process through which strategic decisions actually get made.
About the Speaker
David Duncan is a bestselling author, advisor, and Partner at Disruptive Edge, where he works with senior leadership teams on growth, innovation, and strategic transformation. He is the co-author of Competing Against Luck with Clayton Christensen and the author of The Secret Lives of Customers. Previously, David was a long-time leader at Innosight, where he helped shape many of the firm’s most influential approaches to strategy and innovation, and earlier in his career, he worked at McKinsey & Company. He brings a rare combination of analytical rigor and lived experience in how senior teams actually make—and commit to—strategic decisions.
Suggested Hotels:
Get ready to enjoy New York City’s historic charm during your visit thanks to TIAA’s incredible location in the center of Midtown East NYC. All of the suggested stays below are within a 5-7 minute walk to the venue. Click the name of the hotel to view property details.
The Courtyard Midtown East: A classic, homestyle stay for Marriott Bonvoy members. This option puts you right in the middle of Midtown, making it easy to get just about anywhere you need to go. Enjoy spacious rooms, convenient amenities and easy access to Grand Central Terminal and nearby dining.
The Bernic Hotel NYC: As part of Hilton’s Tapestry Collection, this hotel provides a boutique-style stay with a bit more personality than your typical hotel. Known for its sleek design and welcoming atmosphere in Midtown East, many rooms feature private balconies, providing a rare opportunity to enjoy fresh air and city views. This is a great option for Hilton Rewards members.
Hyatt Grand Central New York: This hotel is ideal for travelers seeking convenience and connectivity. With direct access to Grand Central Terminal, The Hyatt GC offers modern accommodations and easy access to transportation, shopping, and iconic NYC landmarks.
InterContinental New York Barclay: If you’re looking for a blend of historic elegance with a contemporary luxury feel, this landmark Midtown East property is for you. Here you can expect refined rooms, upscale dining, and a sophisticated atmosphere just a short walk from top sights, shopping, and dining. This option is most ideal for IHG Rewards members.
About the venue:
The TIAA Building at 730 Third Avenue is a prominent Midtown East office tower that has served as the longtime headquarters of TIAA since the 1950s. Originally a mid-century corporate building, it has been recently modernized into a Class A office space providing a comfortable and commitment setting to enjoy the Summit.