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• Lead by Experiment: A Practical Approach to Navigating Complexity & AI

  • When
    05/27/2026
  •  
    5:00 PM - 6:30 PM
  • Location
    Canopy Menlo Park

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  In today’s world, leaders are expected to move fast, innovate constantly, and still somehow get everything right. No pressure, right?

  For many high-achieving women, that pressure can quietly turn into overthinking, perfectionism, and hesitation, especially when the stakes feel high, the room is complex, and the margin for error feels very small.

  This interactive session is not about adding another leadership framework to your already full plate. It is about creating something far more powerful: permission to experiment.

  Together, we’ll explore why perfectionism can become the enemy of agility, and how small, safe-to-fail actions can help leaders move from analysis paralysis to meaningful momentum. Through live micro-experiments, Melissa will show how experimentation builds confidence, courage, creativity, and psychological safety. For ourselves and the teams we lead.

  • Date/Time: May 27 at 5:00- 6:30 PM
  • Location; Canopy, Menlo Park

  You’ll leave with a practical way to give yourself, or your team, a “permission slip” to try something new this week.

  What You’ll Walk Away With

  By the end of this session, you will:

  1. Understand why “permission to experiment” is more powerful than traditional creativity training.
  2. Experience a live micro-experiment that helps break through overthinking and analysis paralysis.
  3. Leave with one practical permission slip you can use immediately. 

  About the Speaker!
  

  Melissa Dinwiddie helps leaders turn the "impossible" into reality—without burning out in the process.

  After studying dance at Juilliard, Melissa spent 15 years as a professional artist in Silicon Valley, while also performing as a jazz singer-songwriter and improviser. Now, as an innovation strategist, she brings this creative toolkit to teams at Google, Meta, and Salesforce.

  Through her Create the Impossible™ framework—Play Hard. Make Crap. Learn Fast. Melissa shows analytical minds how to unlock agility and lead with courage through rapid change. Author of Innovation at Work, she's known for interactive sessions that leave audiences energized and ready to try something new.

  
  

  
  

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• Second Act! You’re Not Lost, You’re Outgrowing Your Life

  • When
    06/25/2026
  •  
    5:00 PM - 6:00 PM
  • Location
    Zoom

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  You’re Not Lost, You’re Outgrowing Your Life

  A session for women who've arrived and are ready for more.

  There is a particular kind of restlessness that visits high-achieving women in midcareer. The title is there. The track record is solid. The respect is real. And yet, something quietly insists that there is more. Different. Truer.

  That feeling is not a warning sign. It is a compass.

  Executive coach Colleen Pimentel reframes midlife career restlessness not as a crisis to manage, but as a signal to follow. In this session, she will guide you through a practical framework designed for senior women who are ready to move from confusion to clarity, and from restlessness to reinvention.

  This session is not about walking away from what you have built. It is about building forward from who you are becoming.

  WHAT YOU WILL TAKE AWAY

  1. Clarity over confusion: Understand why the traditional linear career path may no longer fit, and how to name what you actually want next.
  2. Fear reframed as growth: Learn to recognize dissatisfaction as a signal of expansion and build courage without making reckless leaps.
  3. A framework you can use: Leave with a grounded model for sustainable reinvention that honors where you are and where you are going.

  ABOUT THE SPEAKER 

  With a 30-year legacy in Big Tech  (Google, Oracle, etc.) and over 10 career reinventions, Colleen doesn't just understand the climb, she knows how to find your true purpose and master the art of evolving to live it. 

  She is now a dedicated speaker, author and trusted mentor focused on guiding high-achieving individuals toward their next chapter. Colleen shares proven, practical strategies to gain crystal-clear vision, ensure value alignment, and take bold, intentional action. She empowers groups and individuals to move past exhaustion and build a career defined not just by achievement, but by deep, unwavering purpose.

  THIS SESSION IS DESIGNED FOR YOU IF you are a senior woman leader navigating one or more of the following:

  • A career transition or role change you have been quietly considering
  • Leadership fatigue that is not solved by a vacation or a promotion
  • A desire for more aligned impact, but no clear path yet to get there

  Reserve your seat today!

  
  

  
  

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• Public Speaking: Building Confidence, Authenticity, and Engagement

  • When
    07/15/2026
  •  
    4:00 PM - 5:00 PM
  • Location
    Zoom

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  Speak with confidence. Lead with presence.

  
  

  Most leaders are never taught how to speak, they are just expected to. This is a practical, judgment-free session for senior women who want to own the room, not just survive it.

  
  

  Whether you are addressing your board, pitching a new idea, leading a town hall, or simply trying to feel more at ease in the rooms you already belong in, the ability to communicate with confidence changes everything.

  The goal is not to be perfect. It is to be present, clear, and unmistakably you.

  In this hands-on session, executive coach and product leadership veteran Diana Stepner shares the practical techniques she has used and taught across startups, enterprise organizations, and executive coaching engagements. You will leave with tools you can use immediately, in your next meeting, your next presentation, your next conversation that matters.

  • Event Date / Time: July 15 | 4:00 - 5:00  PM PST 
  • Location: Zoom

  What you will take away

  1. Confidence that is yours: Unlock your speaking potential and learn to channel nervous energy as fuel - not a liability.
  2. Authentic delivery: Move past performance mode and into genuine connection with your audience, every time you speak.
  3. Techniques that work: Walk away with proven methods, including Memory Bookends and the Accordion Method, for clear, engaging delivery.

  This session is designed for you if

  • Presentations, pitches, or town halls feel more draining than they should
  • You want to be more compelling without becoming someone you are not
  • You are stepping into higher-visibility roles and want to show up fully

  About the Speaker

  Diana Stepner is a Silicon Valley native who believes in the power of putting people first. She combines deep product leadership experience with a human-centered approach to help ambitious product leaders unlock their full potential.

  Diana’s background includes leadership roles across startups, enterprise organizations, digital agencies, and software consulting, including E.piphany, Cheapflights, SimplePractice, Salesforce, Monster, Pearson, Razorfish, Epsilon, and more. She holds a MIMS from UC Berkeley, an MBA from Boston University, and an ACC credential from the International Coaching Federation.

  Reserve your seat today!

  
  

  
  

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