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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.

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 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

8:00 AM - 9:00 AM

Networking Breakfast

Meet your Chief of Staff peers over coffee, tea, and an amazing buffet style breakfast!
9:00 AM - 9:30 AM

Welcome Session

Kick off the day with our outlook on the development of the Chief of Staff role at successful organizations globally.
Scott Amenta
Founder at Chief of Staff Network
Rahul Desai - Chief of Staff Network General Manager
Rahul Desai
GM at Chief of Staff Network
9:30 AM - 10:15 AM

Outperforming as a CoS

Discover different IQ & EQ strategies for creating leverage and outperformance in your role.
Rachel Peck
Founder & CEO, Metronome
Sophie Kaye
Director & Chief of Staff, Frame.io
10:15 AM - 11:00 AM

Interactive Problem-Solving Hot Seats

Share your challenges and gain insights from fellow CoS professionals.
11:00 AM - 11:30 AM

Founder Fireside Chat

Michael Martocci will share the founding story of SwagUp and talk through some of the consequential decision points along the way, in conversation with Tom Guthrie
Michael Martocci
CEO of SwagUp
11:30 AM - 12:15 PM

Keynote: CEO and CoS Discussion

American businessman, venture capitalist, political strategist, and writer, Bradley Tusk, sits down with his Chief of Staff, Meghan Collins, to share an inside look at their working relationship.
Bradley Tusk
Founder & CEO at Tusk Holdings
Meghan Collins
Chief of Staff at Tusk Holdings
12:15 PM - 12:45 PM

Networking Lunch

Network over lunch and engage with fellow Chiefs of Staff in hand-selected roundtables.
12:45 PM - 1:30 PM

Strategic Planning Workshop

Learn best practices for strategic planning processes and how to spot golden opportunities in these interactive sessions.
emily Smith
Chief of Staff at Lattice
Thea Charles
Chief of Staff, Organizational Effectiveness, Business Insider
1:30 PM - 2:00 PM

AI Lightning Talks

Get inspired by quick, impactful talks on AI advancements and how this next wave of tech can impact and improve your effectiveness.
Michelle Banham
Chief of Staff at You.com
R. A. Farrokhnia
Faculty & Executive Director at Columbia Univeristy
2:15 PM - 3:00 PM

CoS Superpowers

In these facilitated small group sessions you'll learn from two leaders about portfolio management as a CoS and deciding what to work on.
Judy Abad
Partner at Abad Capital
Michelle Mittler
VP, Chief of Staff at Vista Equity Partners
3:00 PM - 3:45 PM

Effective Communication Workshops

Enhance your communication skills with practical storytelling techniques, crisis communications, and tactics to handle hard conversations in these interactive workshops.
Nancy Xu
Exec Coach & Head of Growth at Mochary Method
Sobina Grenderova
Sabina Grenaderova
Corporate Affairs Manager at Macquarie Asset Management
Chris Connelly
CEO, The Stable Way & fmr. CoS, Google Area 120
3:45 PM - 4:15 PM

Small Group Jam Sessions

Tackle leadership challenges and team dynamics in focused, moderated discussion groups.
4:30 PM - 5:00 PM

Closing Session

Recap the day’s highlights and preview upcoming social activities and dinner.
Scott Amenta
Founder at Chief of Staff Network
Rahul Desai - Chief of Staff Network General Manager
Rahul Desai
GM at Chief of Staff Network
5:00 PM - 7:00 PM

Downtime with Optional Activities

Choose from a city tour, speed networking, or other engaging activities with fellow Chiefs of Staff.
9:00 AM - 10:00 AM

Networking Breakfast

Meet your Chief of Staff peers over coffee, tea, and an amazing buffet style breakfast!
10:00 AM - 10:15 AM

Opening Remarks

Kick off the day with a celebration of CoS achievements, sponsor shoutouts and a preview of the upcoming sessions.
Scott Amenta
Founder at Chief of Staff Network
Rahul Desai - Chief of Staff Network General Manager
Rahul Desai
GM at Chief of Staff Network
10:15 AM - 11:00 AM

Winning Strategies: Planning and Execution for Maximum Impact

Master your skills on simplification from complexity, prioritization for measurable value and value creation for all sizes and maturities of businesses.
Eleazar Orellana
fmr. Chief of Staff, Northwestern Mutual
Szilvia Kocsy
Chief of Staff, LinkedIn
11:15 AM - 12:00 PM

Growing Your Business

Learn how to identify growth opportunities and influence your principal to take them on as a CoS.
Piyush Khandekar
CoS to COO, Reddit
Abhishek Vora
CoS to CEO, LaunchDarkly
12:00 PM - 12:45 PM

Networking Lunch

Network freely over lunch and engage with other Chiefs of Staff.
12:45 PM - 1:30 PM

Exiting the CoS Role

Explore strategies for transitioning from the CoS role to new opportunities.
Stella Treas
VP, Chief of Staff to the CEO at GitLab
Dan Katz
VP, Head of Corp Dev at Homeward Health
Juhi Kabra
CoS to CEO, Redesign Health
1:30 PM - 2:30 PM

Debrief, Closing Remarks, and Mingle

Recap of the day’s highlights and a final opportunity to mingle with fellow attendees.
Scott Amenta
Founder at Chief of Staff Network
Rahul Desai - Chief of Staff Network General Manager
Rahul Desai
GM at Chief of Staff Network
2:30 PM - 4:00 PM

Optional: Group NYC Experience

The best strategy minds come together for an exciting NYC walk and scavenger hunt. An unforgettable city experience with your Chief of Staff peers.
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.
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.
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.
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.
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.
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.
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.
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
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
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
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.
Chief of Staff Connect welcomes leaders from the world's biggest and most innovative brands.
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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

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tickets

Limited Early Bird tickets available now!
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Become a Speaker

Have something to share with the Chief of Staff community? Apply here to join Connect as a speaker.
GET STARTEDChief of Staff Connect 2024

Become a Partner

Download our prospectus to learn more about the opportunities available for official sponsors.
BECOME A PARTNERChief of Staff Connect 2024

2025 COSC sponsors

Exclusive Sponsors & Partners

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
  • 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.
LEARN MORE
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.
Heather Higgins
fmr Chief of Staff to CEO, ChartIQ