Chief of Staff Connect New York 2025
The Art of Human Alignment
Join an exceptional group of senior Chief of Staff leaders shaping the future of organizational success.
Oct 22-24, 2025
Times Square, NY
Oct 22: Early registration & evening experience (TBA)
Oct 23: Day 1 interactive talks, workshops and connections + happy hour in Times Square
Oct 24: Day 2 interactive talks, workshops and connections in Times Square


DARA CHEN
Attending the Chief of Staff Connect conference was a highly valuable way to connect with others in the role. It was a practical, engaging way to learn from and connect with the best. I not only left with a treasure trove of best practices but also gained a network of like-minded peers.
EMILIE GRAHL
Overall great conference. I most appreciated the time to network and learn from fellow CoS's, particularly the day 1 problem solving session.


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Where Elite Chiefs of Staff Unite.
Engage with a highly curated group of Chiefs of Staff from top-performing organizations, gaining insights from those driving impact at the forefront of their businesses.
- Chiefs of Staff driving strategic execution and alignment across high-performing organizations.
- Professionals navigating the unique challenges and opportunities of scaling, sustaining growth, or optimizing large, complex operations.
- CoS teams working collaboratively to align leadership priorities, manage cross-functional initiatives, and create operational clarity across the organization.

Inside COSC NEW YORK
Shaping the Future of Organizational
Success
Chief of Staff Connect New York is our premier 2-Day Event for elite Chiefs of Staff.
COSC is built around an essential focus: the role of Chiefs of Staff as the connective force that ensures alignment, collaboration, and execution at the highest levels of an organization. As trusted advisors and strategic operators, Chiefs of Staff excel at creating coherence across teams, systems, and leadership agendas, amplifying their impact with tools like AI to streamline workflows and enable data-driven decision-making.
COSC is built around an essential focus: the role of Chiefs of Staff as the connective force that ensures alignment, collaboration, and execution at the highest levels of an organization. As trusted advisors and strategic operators, Chiefs of Staff excel at creating coherence across teams, systems, and leadership agendas, amplifying their impact with tools like AI to streamline workflows and enable data-driven decision-making.
COSC NEw york 2025 Themes
Not Just a Conference, A Catalyst for Impact
Drivng Organizational Alignment
Explore strategies for aligning leadership priorities, breaking down silos, and fostering seamless collaboration across teams and departments.
Navigating Conflict: Transforming Tension into Team Strength
Explore practical strategies to foster healthy, constructive conflict that strengthens trust, encourages diverse perspectives, and drives better decision-making.
Building Scalable Systems
Through interspersed demos and hands-on workshops, attendees will explore key operational challenges such as managing performance reviews, designing career ladders, and optimizing workflows.
Chief of AI:Leading the Future of Intelligent Operations
Dive into the pivotal role Chiefs of Staff play in evaluating AI solutions, driving adoption across teams, and ensuring responsible use through robust governance and data security practices.
Fostering Culture: Leadership in Times of Change
This theme explores the role of Chiefs of Staff in creating a culture of trust, collaboration, and shared purpose, even in the face of adversity.
15+
Expert Voices
6+
Hands-On Workshops
130+
Senior Chiefs of Staff

Agenda
Don't miss the full
Connect experience

Check-in – 8am
Networking Breakfast
Start your day with intention, connection, and a fresh cup of coffee. Join fellow Chiefs of Staff to set the tone, share what’s ahead, and spark meaningful conversations that will anchor your experience.
Opening – 9:15am
Welcome & Energizer
We’re kicking off Connect with energy, intention, and connection. Join us as we set the tone for the day, share what’s ahead, and spark a few meaningful conversations to get you grounded, excited, and ready to make the most of the room.
Keynote & Workshop – 9:30am
Storytelling for Operators
Storytelling is more than narrative, it’s a tool for operational alignment. Learn how to craft stories that move teams, influence up, down, and across, and bring clarity to complex change.
Breakout Rooms – 10:45am
AI vs. Human Alignment Paths
Choose your alignment path during this unique breakout block.
The "Human Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI Room" will guide you in building AI-powered workflows live with experts, equipping you with practical tools to streamline operations and reduce friction.
The "Human Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI Room" will guide you in building AI-powered workflows live with experts, equipping you with practical tools to streamline operations and reduce friction.
Workshop – 11:30am
Conflict as a Growth Engine: Leading Through Strategic Disagreement
Conflict doesn’t have to break alignment; it can drive it. In this session, you’ll learn frameworks and techniques to navigate disagreement strategically, roleplay real-world misalignment scenarios, and discover how to transform tension into trust and progress within your teams.
Networking – 12:30pm
Collective Experience
Connect organically with Chiefs of Staff at similar stages of AI and operational maturity through a guided networking experience.
You’ll identify and build relationships with peers facing similar challenges and opportunities, ensuring you leave COSC with connections that will support your alignment work long after the event.
You’ll identify and build relationships with peers facing similar challenges and opportunities, ensuring you leave COSC with connections that will support your alignment work long after the event.
Break – 1pm
Networking Lunch
Refuel and recharge while deepening conversations from the morning. This lunch is your chance to reflect, share insights, and continue building meaningful relationships with CoS peers.
Live Case Lab – 2:15pm
Post-Mortems and Missed Signals: A Candid Debrief of a Transformation Gone Wrong
In this interactive live case session, you’ll analyze a real-world transformation that missed its mark, informed by a recorded podcast with an exceptional CEO provided before COSC.
Small groups will unpack what went wrong, draft actionable advice, and hear the CEO’s reflections live, turning a failed transformation into a powerful learning experience you can apply to your own high-stakes projects.
Small groups will unpack what went wrong, draft actionable advice, and hear the CEO’s reflections live, turning a failed transformation into a powerful learning experience you can apply to your own high-stakes projects.
Break / Session – 3:30pm
Optional: Future Self Post Office
Step into a reflective pause with our Future Self Post Office, where you’ll write a postcard to your future self predicting your organization’s alignment challenges and personal leadership goals six months from now.
We’ll mail your note, then capture it in AI to generate an instant prediction for tomorrow, offering a striking contrast between human intuition and AI speed.
We’ll mail your note, then capture it in AI to generate an instant prediction for tomorrow, offering a striking contrast between human intuition and AI speed.
Panel – 4pm
The Future of Alignment: What Work Looks Like in 2035
What will it take to align teams in the decade ahead? This forward-looking panel brings together experienced operators and thought leaders to explore how shifting work models, AI integration, and organizational design will redefine alignment in the years to come.
Closing – 4:45pm
Closing & Networking
We’ll close the day with reflections and open networking over drinks and light bites, giving you space to solidify your learnings, share your insights with fellow Chiefs of Staff, and build new connections that will support your alignment work long after COSC ends.
Happy Hour – 5-7pm
Chief of Staff Mixer
Unwind and connect with fellow Chiefs of Staff over casual conversations, refreshing drinks, and tasty bites. Expand your network in a relaxed and engaging atmosphere.
Check-in – 8am
Networking Breakfast
Ease into Day 2 with a relaxed breakfast alongside fellow Chiefs of Staff. This is your moment to reconnect, reflect on Day 1, and set your intentions for the day ahead with clarity and calm.
Opening – 9:15am
AI Recap
Start the morning with a concise, AI-generated recap of Day 1, highlighting key themes, insights, and takeaways.
Interactive Talk & Workshop – 9:30am
Taste, Judgment, and Power: Honing Executive Sensibility in the Age of AI
In a world where AI scales outputs, your judgment becomes the differentiator. This interactive session uses mini-case vignettes where you will evaluate scenarios, discuss in pairs what’s good or off, and decide whether you would ship or stop it.
You’ll walk away understanding how to guide quality, not just speed, using your executive sensibility to lead in an AI-augmented environment.
You’ll walk away understanding how to guide quality, not just speed, using your executive sensibility to lead in an AI-augmented environment.
Networking – 10:15am
Peer-to-Peer Networking
Join intimate, themed roundtable discussions designed for thoughtful, low-pressure networking with fellow Chiefs of Staff. Each table will focus on a different topic relevant to your role, helping you build deeper connections and gain insights from peers navigating similar challenges.
Workshop – 11:30am
AI or Human? Making the Call
Faced with a hiring decision? A messaging pivot? A strategic call?
In this hands-on workshop, you will work through tough organizational scenarios and debate who’s better for the job—human or machine.
In this hands-on workshop, you will work through tough organizational scenarios and debate who’s better for the job—human or machine.
Break – 12:30pm
Networking Lunch
Refuel while continuing meaningful conversations sparked during the morning.
Interactive Talk & Workshop – 1:30pm
Practical AI Adoption Stories
Learn how Chiefs of Staff are successfully implementing AI solutions in their organizations.
This session explores real case studies of AI transformation at the executive level, balancing efficiency with ethical and secure practices. You’ll leave with practical insights to guide your own responsible AI adoption.
This session explores real case studies of AI transformation at the executive level, balancing efficiency with ethical and secure practices. You’ll leave with practical insights to guide your own responsible AI adoption.
Panel – 2:15pm
The Future of the Chief of Staff Role
As organizations evolve, so does the role of Chief of Staff. This closing talk explores what’s next for the profession in the context of AI integration, organizational complexity, and the need for alignment at scale.
Closing – 3pm
Closing & Networking
We’ll close the day with reflections and open networking over drinks and light bites, giving you space to solidify your learnings, share your insights with fellow Chiefs of Staff, and build new connections that will support your alignment work long after COSC ends.
PRICING
Get your tickets now!
Membership Bundles
Buy a bundled Chief of Staff Connect Ticket Chief and enjoy 1 year of Chief of Staff Network PRO Membership.
Early
Bird
Bird
Price:
$799
Limited Tickets Available
End Date: 5/1/2025
Benefits: Early bird buyers will be enrolled in a raffle for a feature interview episode on the Chief of Staff Podcast!
Regular Registration
Price:
$1,199
Regular Registration ends 10/1/2025
Bundle:
Ticket & PRO Membership
Ticket & PRO Membership
Price:
$1,600
This bundle includes your Chief of Staff Connect NYC ticket and 1 year of CoS Network PRO Membership ($950 value), offering you extended access to the tools, insights, and community to excel in your role.
Group
Tickets
Tickets
Price:
$599
Looking to attend Chief of Staff Connect with 3+ CoS team members? Reach out to us for group pricing!
What Attendees Are Saying
Chief of Staff connect
delivers the results

Meg Rockman
Fractional COO and Chief of Staff, Rockman Consulting
It was SO well conducted! The thoughtful planning and effort that went into it was evident. Thank you for putting on such a great event.

Dara Chen
Chief of Staff to CEO, Rad AI
Attending the Chief of Staff Connect conference was a highly valuable way to connect with others in the role. It was a practical, engaging way to learn from and connect with the best. I not only left with a treasure trove of best practices but also gained a network of like-minded peers.

Zoe Cornish
Chief of Staff and Culture, BrightLocal
It was a brilliant event with lots of practical takeaways.Coming from the UK, I did wonder if the content would be US-centric; however, it was all super relevant.
Speakers
Experience The Industry’s Leading Thinkers on Organizational Excellence

Tim Armstrong
Founder & CEO at Flowcode
fmr. Chairman & CEO at AOL

Dominique Lear
Chief of Staff at Incandescent

Rachel Peck
Founder & CEO at Metronome
fmr. Chief of Staff at Harry's

Juhi Kabra
Founder & Executive Coach
at Juhi Kabra Coaching
fmr. Chief of Staff at Redesign Health

Eric Osman
Founder & CEO at Mockingbird
Become a Speaker
Have something to share with the Chief of Staff community? Apply here to join Connect as a speaker.
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Download our prospectus to learn more about the opportunities available for official sponsors.
BECOME A PARTNER
COSC is proudly presented by the Chief of Staff Network.
The CoS Network brings a group of solution oriented minds together into an environment set up for collaboration and sharing of best practices.
Benefits of PRO Membership
Benefits of PRO Membership
- Local Events & Braintrusts
- Research & reports
- Highly engaged community of peers
- Fundamentals Course and Power Skills Certification


Buy a cosc ticket,
enjoy 1 year of PRO membership
Buy a bundled ticket to any Chief of Staff Connect event and get access to PRO Membership for 1 year.
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Over the three years I've been a member, I've grown my skills and confidence as a Chief of Staff thanks to the diverse, supportive community and the many, varied professional development opportunities and resources.
I'm so grateful to be a part of the Chief of Staff Network.
I'm so grateful to be a part of the Chief of Staff Network.