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: Evening Mixer (Flatiron)
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 – 9:00am
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.
Scott Amenta
Founder at Chief of Staff Network
Tom Guthrie
President at Chief of Staff Network
Keynote & Workshop – 9:15am
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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.
Juhi Kabra
Founder & Executive Coach at Juhi Kabra Coaching
andrea Mayendia
Chief of Staff to CTO/CPO at Dow Jones
Artem Fishman
Chief Product & Technology Officer at Dow Jones
Networking – 10:15pm
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.
Victoria Farris
Consultant. Speaker. Coach. at Farris Consulting
Breakout Rooms – 11:00am
AI vs. Human Alignment Paths
Choose your alignment path during this unique breakout block.
The "Human-Centered Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI-Powered 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-Centered Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI-Powered Room" will guide you in building AI-powered workflows live with experts, equipping you with practical tools to streamline operations and reduce friction.
Lola Martinez
Program Director at Reforesters Laboratory & NYC Guide at Othership
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.
Rachel Peck
Founder & CEO at Metronome Consulting
fmr. Chief of Staff at Harry's
fmr. Chief of Staff at Harry's
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.
Tim Armstrong
Founder & CEO at Flowcode
fmr. Chairman & CEO at AOL
fmr. Chairman & CEO at AOL
Breakout Rooms – 3:30pm
AI vs. Human Alignment Paths
Choose your alignment path during this unique breakout block.
The "Human-Centered Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI-Powered 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-Centered Room" will help you deepen trust, refine your communication style, and strengthen relational influence inside your organization.
The "AI-Powered Room" will guide you in building AI-powered workflows live with experts, equipping you with practical tools to streamline operations and reduce friction.
Lola Martinez
Program Director at Reforesters Laboratory & NYC Guide at Othership
Workshop – 4pm
Systems Thinking for Chiefs of Staff: Three Altitudes, One Operating System
Chiefs of Staff are the engines of alignment. This session gives you a compact operating system across three altitudes—partnering with your principal, orchestrating the leadership team, and coordinating cross‑functional execution—so AI amplifies your impact without replacing judgment.
Using a simple systems frame—Objects, Questions, Actions—you’ll design a weekly cadence, decision pathways, and communication loops. We’ll pinpoint where AI speeds prep, synthesis, and follow‑through, and where human discretion must lead for ethics, politics, and relationships.You’ll leave with a usable blueprint: lightweight rituals, artifacts, and prompts that clarify priorities, tighten handoffs, and improve reliability.
Using a simple systems frame—Objects, Questions, Actions—you’ll design a weekly cadence, decision pathways, and communication loops. We’ll pinpoint where AI speeds prep, synthesis, and follow‑through, and where human discretion must lead for ethics, politics, and relationships.You’ll leave with a usable blueprint: lightweight rituals, artifacts, and prompts that clarify priorities, tighten handoffs, and improve reliability.
Jamie White
Chief of Staff, Marketing at Notion
Closing – 5pm
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.
Scott Amenta
Founder at Chief of Staff Network
Tom Guthrie
President at Chief of Staff Network
Happy Hour – 5-6pm
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 – 9am
Day 1 Recap
Start the morning with a concise, AI-generated recap of Day 1, highlighting key themes, insights, and takeaways.
Scott Amenta
Founder at Chief of Staff Network
Tom Guthrie
President at Chief of Staff Network
Workshop – 9am
Beyond the Plan: The Human Side of AI Transformation
We've all seen great organizational transformation programs fail because we have forgotten that organizations are made up of humans.
Messy, complex, fearful, hopeful humans who deserve more than Gantt Charts and PowerPoints to help them reimagine their current ways of working (and follow through on that change!). Unlocking the organizational potential promised by AI depends on our ability to help individuals see, understand, and ultimately navigate their internal barriers to change.
Messy, complex, fearful, hopeful humans who deserve more than Gantt Charts and PowerPoints to help them reimagine their current ways of working (and follow through on that change!). Unlocking the organizational potential promised by AI depends on our ability to help individuals see, understand, and ultimately navigate their internal barriers to change.
Dominique Lear
Chief of Staff at Incandescent
Breakout – 10:20am
Building AI-First Operational Systems
Learn how Chiefs of Staff can design scalable, AI-driven workflows that extend executive capacity and fuel company growth.
This workshop introduces a 3-Pronged AI Adoption Framework to help you create operational leverage that scales with the business—not headcount. Walk away with practical strategies to multiply founder and executive bandwidth through smarter, AI-first systems.
This workshop introduces a 3-Pronged AI Adoption Framework to help you create operational leverage that scales with the business—not headcount. Walk away with practical strategies to multiply founder and executive bandwidth through smarter, AI-first systems.
Justin St-Louis Wood
Strategic Initiatives & AI Operations at Novisto
Breakout – 10:20am
Navigating the Nervous System: Leadership, Trust, and Culture Beyond AI
In today’s AI-driven world, efficiency and data can be automated, but human
connection, trust, and culture cannot. This engaging, interactive conversation explores how your
nervous system shapes presence, decision-making, and team dynamics in ways that no
technology can replicate.
Learn how stress, regulation, and embodiment directly impact
leadership effectiveness, and leave with practical tools to cultivate calm, clarity, and presence in high-stakes situations.
connection, trust, and culture cannot. This engaging, interactive conversation explores how your
nervous system shapes presence, decision-making, and team dynamics in ways that no
technology can replicate.
Learn how stress, regulation, and embodiment directly impact
leadership effectiveness, and leave with practical tools to cultivate calm, clarity, and presence in high-stakes situations.
Victoria Farris
Consultant. Speaker. Coach. at Farris Consulting
Workshop – 11:15am
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.
This session includes a pre-recorded podcast episode and case styudy to prepare.
In this hands-on workshop, you will work through tough organizational scenarios and debate who’s better for the job—human or machine.
This session includes a pre-recorded podcast episode and case styudy to prepare.
Eric Osman
Founder & CEO at Mockingbird
Tom Guthrie
President at Chief of Staff Network
Break – 12:30pm
Networking & Lunch
Refuel while continuing meaningful conversations sparked during the morning.
Panel – 1:30pm
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.
Michael Martocci
Founder & CEO at SwagUp
Kyle Hagge
Chief of Staff, CEO at Morning Brew
Scott Amenta
Founder at Chief of Staff Network & Co-founder / Head of Product at Sylva
Interactive Talk & Workshop – 2:00pm
Driving AI Transformation: Aligning Execs & Operationalizing Change
AI adoption isn’t just a tech rollout, it’s an organizational shift that requires alignment at the highest level.
In this session, Ana Silva, Chief of Staff at Section, will walk through real-world case studies of leading successful AI transformations: aligning executive stakeholders, driving adoption, and building systems that balance efficiency, ethics, and trust.Participants will have the opportunity to map their own organization’s readiness and identify the next steps to lead AI initiatives from the inside.
In this session, Ana Silva, Chief of Staff at Section, will walk through real-world case studies of leading successful AI transformations: aligning executive stakeholders, driving adoption, and building systems that balance efficiency, ethics, and trust.Participants will have the opportunity to map their own organization’s readiness and identify the next steps to lead AI initiatives from the inside.
Ana Flávia Silva
Chief of Staff to the COO at Section
Closing – 3pm
Closing & Networking
We’ll close the day with reflections and open networking 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.
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
Ana Flávia Silva
Chief of Staff to the COO at Section
Justin St-Louis Wood
Strategic Initiatives & AI Operations at Novisto
Michael Martocci
Founder, CEO at SwagUp
Jamie White
Chief of Staff, Marketing at Notion
Andrea Mayendia
Chief of Staff to CTO/CPO
at Dow Jones
Artem Fishman
Chief Product & Technology Officer at Dow Jones
Victoria Farris
Consultant, Speaker, Coach.at Farris Consulting
Kyle Hagge
Chief of Staff, CEO at Morning Brew
Lola Martinez
Program Director at Reforesters Laboratory & NYC Guide at Othership
TICKETS
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
Late Registration
Price:
$1,399
Late Registration ends 10/19/2025
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
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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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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Become a Partner
Download our prospectus to learn more about the opportunities available for official sponsors.
BECOME A PARTNER2025 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
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.
FAQs
Here are the most common questions we receive. If you have any further questions, the best thing to do is reach out to a member of our team!
Register todayIs there a hotel room block?
We don’t have a formal block, but here are nearby options within a short walk of the venue:
- Casablanca Hotel - 4 star - ~ 500 a night (closest, 300 ft away)
- Hampton Inn Manhattan/Times Square - 3 star - ~ 500 a night
- Courtyard NY Manhattan Times Square - 3 star - ~500 a night
- Knickerbocker - 4 star - ~ 600 a night
Further out - 10-15 minute walk
- Michaelangelo - 4 star - ~480 a night
- Courtyard NYC Manhattan Central Park - 3 star - ~440 a night
What is the refund policy?
Can’t make it? We’ll refund your ticket in full until September 1. After that date, we ask that you transfer your ticket to another Chief of Staff at your organization or you may apply the cost of your ticket to CoS Network PRO Membership.
Do you offer group discounts?
Yes! Bringing 3+ Chiefs of Staff from your company? Reach out to us for a special group rate.
Do you offer discounts for nonprofits?
We’re eager to support nonprofit leaders. Email hi@chiefofstaff.network to request a nonprofit discount.
Who should attend Connect?
Senior Chiefs of Staff from high-growth startups, large enterprises, government, universities, and nonprofits. If you’re shaping strategy and driving execution, especially in AI at the executive level, Connect is for you.
What is PRO+ Membership?
PRO+ includes:
- Full CoS Network Membership (private Slack, courses, and programs)
- A ticket to Chief of Staff Connect 2025 (NY or Europe)
- Locked-in pricing for next year’s conferences
To get started, Apply for Membership Here.
Is there a pre-conference mixer?
Yes! Join us on October 22, 5-7pm for an optional evening Mixer just steps from the venue. It’s your chance to meet fellow Chiefs of Staff in a relaxed setting before diving into two days of content and connection.