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We just wrapped up our seventh annual S2G Summit, celebrating our tenth anniversary as a firm. The two-day event was jam-packed with thought-provoking presentations and discussions. In this post and the next one, we’ll share some of the highlights with you. Every year, the first day of the Summit is our Portfolio Executive Leadership Day, where we bring together many of our portfolio company leaders to learn and discuss topics that are top of mind for them. This year, the theme of the day was Leading Through the Transition, and presentations and workshops focused on the future of work, category creation, and AI. 

To kick off the day, Rishad Tobaccowala, former Chief Growth Officer at Publicis Group, an advertising and communications firm with approximately 100,000 employees worldwide, shared insights aimed at helping leaders assess and pivot their strategies to align with the changing business landscape. He outlined four major shifts reshaping the global business environment: 1) a geographical power shift from the West to the East, 2) a transition of influence from management to talent, 3) the movement from large corporations to smaller companies due to their net new job creation, and 4) significant demographic changes. As he stated, the technological evolution, starting from the advent of the internet to the current landscape shaped by AI, VR, and blockchain, calls for a reevaluation of how corporations are designed to leverage these advancements effectively.

Rishad also touched upon the changing motivations behind work. Beyond traditional drivers like money, fame, and power, there is a growing emphasis on purpose, value, connection, and personal growth. He explored the implications of these shifts, particularly focusing on the transformation in work culture and talent management strategies. He emphasized three critical questions that leaders should constantly ask themselves to remain relevant: 1) Is the current business model still appropriate? 2) Does the organizational structure have the right partners and talent to succeed? 3) Is the leadership still relevant in today's context? Aligning with these trends and exploring these questions is key to building a future competitive advantage.

According to Rishad, the foundational shift is not just about reimagining companies or work but about reimagining the very essence of our professional identities and communities in this dynamically changing world. His closing thoughts revolved around the imperative for openness to change, urging leaders to engage in meaningful dialogues about creating more adaptive, inclusive, and innovative work environments to thrive in the future. 

After Rishad’s talk, company leaders were divided into tracks and rotated through three different sessions. 

Becoming a Category King 

Our first session was an interactive workshop with the team from Play Bigger, which helps companies think about moving beyond innovation to tackling category design in order to create and monetize new markets. The idea is that just being faster, cheaper, and better will still leave you competing in an existing category and with much less of an advantage over the incumbent. The Play Bigger philosophy emphasizes that a great problem is necessary to set the category potential, and it is crucial that the problem be big enough to build a business around.

The Play Bigger team had done prework in the form of employee interviews with a few portfolio companies, and they presented their analysis to demonstrate their method. They shared the results of their analysis on the context, problem, villain, and consequences of a company strategy while our entrepreneurs participated in discussions to understand the category potential of their businesses. 

S2G AI Challenge

In this session, Vikram Sharma, Operating Partner at S2G, led our entrepreneurs through an exercise to consider the role and potential that AI can play in their companies. AI increasingly holds great potential for so many aspects of businesses and the workplace, with 72 percent of people expecting conversational AI and voice assistants to be mainstream in business in the next one to five years.

Entrepreneurs gathered in groups to network, collaborate, and design a chatbot solution for one or more of the group’s businesses, and then present their ideas to the larger group. The solutions included a chatbot that provides system functioning requirements to determine the lowest cost for the highest output, a chatbot for filing regulatory documentation, a reality chatbot that orchestrates, manages, and verifies all the other generative AI tools in a business, and a supply chain chatbot which could predict commodity pricing trends. 

The Future of Work

Entrepreneurs had the opportunity to dive a little deeper with Rishad Tobaccowala on how to lead and manage culture in a changing workplace. He highlighted the individual benefits of hybrid remote work, such as more family time and reduced commuting, alongside the advantages for companies, including enhanced hiring flexibility. But this has to be balanced with the significance of in-person interactions.

Rishad proposed finding an optimal blend of work models that aims for the best outcome with minimal resistance. He emphasized that it takes great leadership to create a strong culture, focused on cultivating excellence in talent, financial results, and products. Rishad also underscored the importance of maintaining a growth mindset, acknowledging realities, and fostering open communication. To close, he advocated for continuous learning and thoughtful reflection on emerging trends and challenges, encouraging leaders to adapt and thrive in the evolving workplace landscape.

Getting our portfolio companies together to share ideas and insights is truly one of our annual highlights, and this year did not disappoint. Stay tuned for our recap of Summit day two. And check out our most recent podcast episode that takes a deeper dive into the future of work with Rishad Tobaccowala. 

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S2G Summit Portfolio Day: Leading Through the Transition

S2G Summit Portfolio Day: Leading Through the Transition


Chuck Templeton

Managing Partner

Chuck Templeton is a long-time entrepreneur who has a deep passion for helping early-stage and emerging entrepreneurs and companies scale their businesses. He is focused on helping entrepreneurs use their business innovations to find solutions to the most urgent environmental and societal problems facing humanity today.


Josie Lane

Art Director

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