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About the Event
Being a CEO can be both exhilarating and isolating—but it doesn’t have to be. Ctrl+Alt+Retreat is a full-day experience designed for CEOs who are navigating the relentless demands and unique challenges of building transformational companies. This retreat offers you the space to reset, connect, and recharge—surrounded by peers who understand the weight and promise of your journey.
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The Details
Date: Friday, June 13, 2025
9:30 AM - 5:00 PM (Check In: 8:30-9:30 AM)
The Engine
750 Main St, Cambridge, MA 02139, USA The Event Space, 1st Floor
Parking: We encourage you to use SpotHero to find a spot at a nearby garage or other local parking options. Please allow extra time for parking and arrival.
Agenda & Details
Scroll right to view the agenda and programming for the day.
Registration, Breakfast, & Headshots
8:30 am | Location: Lobby & Front Gallery
Check in and enjoy breakfast. Professional headshots will be available in the Back Gallery. Dress however you see fit.
Welcome & Framing the Day: Theme of Resilience
9:30 am | Location: Event Space
Opening remarks to set the tone for the day, with a focus on resilience in leadership.
- Emily Knight, CEO & President, The Engine
- Jaye Goldstein, Executive in Residence, The Engine
- Dr. Rachel Barbanel-Fried, Clinical Psychologist & Executive Coach
Speed Chats by Sector
10:00 am | Location: Gallery Space
Connect in small groups with CEOs from your sector—health, climate, or advanced systems—for rapid networking and shared insights.
- Health: Front Gallery
- Climate: Back Gallery
- Advanced Systems & Infrastructure: Left Gallery
Speed Chats by Stage
10:30 am | Location: Gallery Space
Join peers at similar company stages (pre-seed, seed, A+, non-profit, etc.) for targeted discussion and advice.
- Pre-Seed: Front Gallery
- Seed: Back Gallery
- Series A or Later: Left Gallery
Choose Your Own Adventure #1
11:00 am | Location: Gallery Space
Select a topic that resonates most with your current challenges and dive deep in focused, small-group discussions.
- Raising Funds: Event Space
- People Management: 1F
- Managing Up With Your Board: 1B
- Co-Founder Relations: 1A
- Product + Technology Development: 1G
Lunch: Building Your & Your Team’s Resilience
12:00 pm | Location: 1st Floor Conference Rooms
A facilitated lunch conversation about building resilience for yourself and your team, led by experienced coaches.
Infrastructure Pre-Seed: Rebecca Anders, 1E
Infrastructure Seed, A or Later: Liza Shirazi, 1F
Climate Pre-Seed: Ben Herbstmann, Event Space Left
Climate Seed: Katherine Otway, 1H
Climate Series A or Later: Jaye Goldstein, 1I
Human Health Pre-Seed Group 1: Cait Tolman, 1A
Human Health Pre-Seed, Group 2: Tiana Veldwisch, 1B
Human Health Seed, Group 1: Sarah Milby, Event Space Right
Human Health Seed, Group 2: Becky Bermont, Event Space Center
Human Health Series A or Later: Rachel Barbanel-Fried, 1G
Choose Your Own Adventure #2
1:00 pm | Location: 1st Floor Conference Rooms
Pick a new, second topic for another round of interactive, peer-driven learning.
- Raising Funds: Event Space
- People Management: 1F
- Managing Up With Your Board: 1B
- Co-Founder Relations: 1A
- Product + Technology Development: 1G
Self-Management Sessions #1
2:00 pm | Location: 1st Floor Conference Rooms
Choose from a range of practical workshops designed to help you leverage technology, enhance productivity, and develop effective strategies for managing leadership challenges.
- Leveraging AI: Event Space
- Reducing Every Day Stress: 1F
- Health + Wellness: 1B
- Productivity: 1G
- Walk + Talk: Patio
Self-Management Sessions #2
2:35 pm | Location: 1st Floor Conference Rooms
Select a second workshop to further deepen your skills in areas like technology adoption, productivity, and effective leadership practice.
- Leveraging AI: Event Space
- Reducing Every Day Stress: 1F
- Health + Wellness: 1B
- Productivity: 1G
- Walk + Talk: Patio
Resilience Conversation & Reflections
3:05 pm | Location: Event Space
Join a closing conversation on resilience with Dr. Namita Bisaria, followed by group reflections to wrap up the day.
Happy Hour
3:45 pm | Location: Patio
Unwind, network, and continue conversations, in an informal setting.
Meet the Coaches
Executive Coaches
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Becky Bermont
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Benjamin Herbstmann
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Cait Tolman
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Jaye Goldstein
Jaye Goldstein Jaye Goldstein is the Executive in Residence for The Engine. Her role focuses on designing our strategy and building robust data systems to measure outcomes. Jaye is also the CEO + Founder of Founder to Leader; she has spent 20+ years working at the intersection of education and innovation at places like Petri, MIT and Harvard.
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Katherine Otway
Katherine Otway Katherine Otway, Chief Marketing Officer at The Engine, is a marketing executive with over 20 years of building customer-centric brands and driving growth. She served as Chief Marketing Officer at Zapata AI, an Engine Ventures portfolio company focused on generative AI software for enterprises. Her track record includes a decade of designing new ventures at IDEO, advising startups and accelerators on marketing strategy, delivering executive education for Kellogg and Babson, and developing entrepreneurial ecosystems abroad.
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Liza Shirazi
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Dr. Rachel Barbanel-Fried
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Rebecca Anders
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Sarah Milby
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Tiana Veldwisch
