Discover the essential building blocks of a portfolio career strategy. This session includes a real-life example of someone’s journey to align their passions, define their personal purpose, and build a diverse portfolio for a fulfilling plural career.
This session explores Venture Capital with a focus on seed-stage investments and the role of advisors. Learn how VC firms operate, startup funding stages, and what founders need at each phase. Featuring insights from VC experts and a startup founder.
This session reframes Brand Management as a strategic lever for building a successful portfolio career, not a superficial marketing exercise. We will demystify what an executive brand truly is, why it matters far earlier than most leaders assume, and how it directly shapes access to board seats, advisory roles, and broader portfolio opportunities. The session will make the mechanics tangible, demonstrate how intentional positioning creates pull instead of reactive hustle, and highlight the importance of doing this work well in advance of any transition. It will conclude with a practical activation exercise to help participants clarify and align their narrative with the portfolio career they want to build.
A strong personal network is a nice-to-have during the operating career, but paramount for portfolio career success. This session covers strategies for identifying and prioritizing existing connections, establishing new relationships intentionally, and nurturing your personal network. Learn how to map your network, manage touchpoints, and maximize impact.
This session helps you assess whether a board role is right for you. Explore what board service entails, key differences between private and public boards, and practical factors like travel, risk, and resilience. Learn how AI is creating new opportunities for leaders.
This session explores how to navigate the path into the boardroom. It will introduce the NYSE Board Services program as a structured pathway into board service and feature firsthand insights from her journey into the boardroom. Drawing on her experience, she will share practical lessons on positioning, credibility, sponsorship, and the realities of the selection process, offering a candid perspective on what it truly takes to secure and succeed in a board role.
This panel will feature an open discussion on the organic path into the boardroom and how opportunities develop through networks, reputation, and operating experience. Panellists will compare startup, private, public, and non-profit boards, highlighting differences in expectations, governance, and value creation. The conversation will also explore how board dynamics and selection processes vary across geographies, offering practical insights for executives considering board roles in different markets.
This session explores why AI must become the portfolio executive’s co-pilot. As leaders transition from full-time operating roles into board and advisory positions, they lose the infrastructure that once supported them, including EAs, chiefs of staff, strategy teams, and research analysts. AI becomes the new support layer, enabling them to manage complexity, prepare for board work, sharpen thinking, and operate with leverage. At the same time, their credibility in the boardroom will increasingly depend on their ability to guide AI-driven enterprise transformation. We will examine how executives can both build personal AI fluency and visibly demonstrate AI domain expertise, ensuring that their market relevance and board impact are unmistakable.
Monday September 7, 2026 10:30am - 11:10am PDT Laugaras Lagoon
In addition to upskilling existing teams, delivering meaningful AI-driven business transformation requires attracting and integrating additional AI-native talent. This fireside chat will explore what it takes to compete for world-class AI professionals in today’s highly dynamic market, from sourcing and positioning to assessing, onboarding, and retaining top talent. We will share practical insights on building credible AI teams that can move from experimentation to real enterprise impact.
Monday September 7, 2026 11:10am - 11:30am PDT Laugaras Lagoon
This session demystifies coaching and consulting as portfolio career paths. We will explore the spectrum of coaching modalities, from informal mentorship and advisory relationships to formal, certified executive coaching. In parallel, we will examine consulting pathways, from operating as an independent consultant to joining established strategy or advisory firms. The session will also address how executives without a traditional consulting background can grow organically into advisory and consulting roles, building credibility, structure, and client traction over time.
Monday September 7, 2026 11:30am - 12:00pm PDT Laugaras Lagoon
Having explored the different pathways, roles, and experiences throughout the retreat, this workshop is the most important moment to put pen to paper and intentionally design your downrange portfolio career strategy. We will give you dedicated time to synthesize the key learnings and begin visualizing what your second career could look like in practice. Surrounded by a stunning natural landscape, this is an opportunity to think expansively, get creative, and unleash your hidden (or not so hidden), artistic talents as you shape your next chapter.
Monday September 7, 2026 1:00pm - 2:00pm PDT Laugaras Lagoon
This session is dedicated to sharing your portfolio career visualizations with the group, inviting thoughtful and constructive feedback, and sharpening your thinking through open dialogue. Each participant will present their portfolio career strategy and immediate commitments, while collectively identifying how the cohort can actively support one another in transforming individual visions into tangible outcomes.
Tuesday September 8, 2026 1:00pm - 4:30pm PDT Blue LagoonNorðurljósavegur 9, 240 Grindavík, Iceland
This session explores how executive coaching can support a portfolio career transition, emphasizing the value of accountability partners and how portfolio career coaching differs from traditional professional development coaching.
Tuesday September 8, 2026 4:30pm - 4:45pm PDT Blue LagoonNorðurljósavegur 9, 240 Grindavík, Iceland
Receive an update on Insight Partners’ Empower program, designed to help executives activate and accelerate their post-operating career preparation. The session will include a brief demonstration of the Empower platform, powered by Diligent, showcasing how it supports board readiness and portfolio career execution.
Tuesday September 8, 2026 4:45pm - 5:00pm PDT Blue LagoonNorðurljósavegur 9, 240 Grindavík, Iceland
