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True Leadership Summit in San Francisco: Supporting Your Whole Team

By Caroline Ciaramitaro and Mikaela Lipsky, April 19, 2024

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Sam at Shack15

At True, we’ve long been dedicated to creating spaces of deep psychological safety so founders are empowered to do their best work, take big risks, and pursue wild ideas. 

To extend that ethos of support to the leadership teams of True Portfolio companies, we’ve designed a series of Leadership Summits to give senior leaders and executives that same kind of space for reflection, skill building, and connecting with peers in similar roles. 

We hosted our most recent True Leadership Summit at the Shack15 coworking space in San Francisco’s Ferry Building where portfolio leaders convened for discussions on scaling engineering teams effectively, operations best practices, mitigating burnout, and examples of effective internal communications stacks. 

Leadership Lessons With Toni Schneider

The event began with a fireside chat on leadership lessons from the storied career of Toni Schneider, a partner here at True and the interim CEO at Automattic as the company’s founder, Matt Mullenweg, takes a very well-earned sabbatical. Our VP of Culture, Madeline Minshew, prompted Toni to share what it’s been like to jump back into the CEO seat, defining qualities of great leaders he’s mentored through the years, and leadership gaps Toni’s recognized in himself – a moment that we hope set the tone for the day in encouraging attendees to speak candidly among one another.  

“It’s hard to stay creative and keep an expansive mindset when we’re all overloaded with messages and demands for our time,” shared Toni.  “I find that if I’m overthinking something — whether a strategy or how to lead a certain department best – I’m usually under-feeling and missing signals for how to move forward next. It’s tough to listen to that inner voice and instinct when we’re all moving at a rapid pace.” 

Fireside Chat

Deep-Dive Discussions & Reflective Prompts

For the remainder of the day, attendees gathered in small groups based on their functional role and industries. To get the conversations going, we posed questions to attendees, prompting them to look inward and identify areas where they can grow as leaders and refine their own departmental strategies. 

If you’re a startup leader and would like to DIY your own leadership reflection, try these prompts we shared at the summit: 

  1. Grab a notebook or open a doc, set a timer for five minutes, and answer the following question: What’s one thing holding you back from being the leader you want to be?
  2. Next, rate your organization’s quality of Communication, Trust, Collaboration, and Conflict Resolution on a scale of 1-5 with 5 being the best. To encourage decisiveness, no 3s allowed.  When finished, jot down a few notes on why you rated each area with the number that you did and consider what’s needed to increase effectiveness in those areas.

See You in NYC Next

Next up, we look forward to meeting more senior and executive leaders from across our portfolio at our True Leadership Summit in NYC on May 9th. If you’re a leader at one of our portfolio companies, talk to your founder about attending. We’d love to have you!

Chalon in Discussion


Shack15, Our Location for the SF Leadership Summit


Portfolio leaders discussing challenges and room for growth

Discussion Deep Dive

Jillian at the Fireside Chat

Happy Hour Following Our Summit

Oysters at Hog Island Happy Hour

True Team at SF Leadership Summit