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Chapter Events

Paris CoS Meetup (Apr 14)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Paris this April. Building on the momentum of our previous gatherings, this next meetup will continue strengthening a high-trust community of Chiefs of Staff and senior operators across Paris. Date & Time: Tuesday, April 14, 2026 · 4:00 PM – 6:00 PM CET Location: Shared upon confirmation of attendance This facilitated, in-person market meetup will bring together Chiefs of Staff and adjacent operators for a structured conversation centered on: Scaling the Chief of Staff Function with Claude As the CoS role matures within organizations, many operators face similar questions: How do you scale the function? How do you move from reactive support to strategic leverage? And how can tools like Claude support clarity, efficiency, and impact? The evening will include moderated discussion and a featured CoS speaker (to be confirmed), alongside open peer dialogue to explore practical approaches and lessons learned. What to expect: A structured, facilitated conversation with a clear theme Practical insights on scaling the CoS function Peer exchange with experienced Chiefs of Staff and operators A small, curated group to encourage thoughtful participation Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re navigating how to evolve and scale your impact as a Chief of Staff, we’d love to have you join us. Attendance will be capped to maintain an intimate and high-quality discussion — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Apr 21

Leadership at Human Speed: A Workshop for Chiefs of Staff

Leadership at Human Speed: A Workshop for Chiefs of Staff Hosted by The GRIN Labs in partnership with The Purpose Project, Tuesday, April 21 This workshop draws on themes from the HumanX Executive Roundtable, Leadership at Human Speed, held April 6 in San Francisco, where senior leaders gathered to explore what high performance looks like when speed, consequence, and human complexity meet. We're bringing that conversation to you. About This Workshop You see everything. The tension before the meeting starts. The decision that moved too fast. The misalignment nobody named. The conversation the leadership team keeps avoiding. You hold the thread of the organization, often without the authority to pull it. And now, with AI accelerating everything, that pace is becoming the norm. But the real question isn't how fast you can move. It's who you are becoming by agreeing to that speed. AI is not just changing what gets done. It is shaping how decisions happen, faster cycles, less reflection, fewer pauses. Without intention, it trains leaders to move before they fully see or understand. This workshop is not about resisting AI. It's about using it without losing yourself in it. Not as something that speeds everything up, but as a partner that can hold information and create space for better thinking. We won't focus on tools or productivity frameworks. We'll slow down just enough to see clearly. What We'll Explore Together How you show up under pressure — and how that shifts as speed increases The patterns AI cannot see, but can amplify Where human judgment must lead in AI-shaped environments How to use AI to create space for clearer thinking and better conversations What You'll Walk Away With A clearer view of your patterns under pressure in fast-moving environments Language for a conversation you've been circling A simple practice to slow down in real time before high-stakes moments How This Works This is not a webinar. There is no slide deck. This is a live, hands-on session built for real conversation and reflection. Camera and audio on, this work happens in relationship. Come with something real: a moment of pressure, a stuck decision, or a dynamic that feels unclear. In a fast-moving world, presence is a leadership advantage. Facilitated by Carl Miller and Michaela Zuckova, Partners at The GRIN Labs and co-founders of The Purpose Project, a growing movement built on one belief: When people learn to notice instead of react, everything changes.

Apr 21

Austin CoS Happy Hour (4/21)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Austin for our second gathering of 2026. After a fantastic kickoff earlier this year with a thoughtful panel discussion and strong turnout from the local CoS community, we’re keeping the momentum going with a more casual happy hour meetup designed for conversation and connection. A special thank you to Kelley Henry for continuing to host and support the growth of the Chief of Staff community in Austin. Date & Time: April 21, 2026 · 5:30 PM – 7:30 PM CT Location: TBD (Austin – shared upon confirmation) This informal gathering will bring together Chiefs of Staff and senior operators across Austin for relaxed conversation, shared experiences, and meaningful peer connections. Unlike our first meetup, which featured a panel discussion, this event will be a casual networking happy hour — giving everyone more time to connect directly with fellow Chiefs of Staff and operators navigating similar leadership challenges. What to expect A relaxed, casual happy hour environment Meaningful conversations with fellow Chiefs of Staff and operators Opportunities to exchange ideas, challenges, and lessons learned New connections within Austin’s growing CoS community Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in connecting with other operators and helping grow the Chief of Staff community in Austin, we’d love to have you join us. Attendance will be capped to keep the gathering intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Apr 21

Dallas Chief of Staff Meetup (Tue Apr 21)

We’re excited to host the second Chief of Staff Network (COSN) meetup of 2026 in Dallas. A special thank you to Darshan Amin and Akinwunmi Akinwande for generously hosting and supporting the continued growth of the Chief of Staff community in Dallas. Date & Time: April 21, 2026 at 6 PM Location: Shared upon confirmation of attendance This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators across Dallas for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. Following a strong start to the year, this meetup is focused on deepening relationships, sharing experiences, and building momentum for the Dallas community in 2026. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Dallas chapter, followed by open networking and shared stories from your experiences supporting founders and senior leadership. What to expect: A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Updates on plans for the Dallas chapter in 2026 A small, curated group to encourage deeper connection Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape the next phase of the Chief of Staff community in Dallas this year, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Apr 22

Chicago Chief of Staff Meetup (Wed Apr 22)

We’re excited to bring the Chief of Staff Network (COSN) community together in Chicago for our first meetup of 2026. As we head into Q2, this gathering is focused on bringing together Chiefs of Staff and senior operators across Chicago to build stronger local connections and continue growing a high-trust community in the city. A special thank you to Jen Kaufmann for generously hosting and helping bring the Chicago CoS community together. Date & Time: Wednesday, April 22, 2026 · 6:00 PM – 9:00 PM CT Location: Shared upon confirmation This informal, in-person meetup will bring together Chiefs of Staff and adjacent operators for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Chicago chapter, followed by open networking and shared conversations with peers navigating similar challenges and opportunities. Whether you’re looking to exchange ideas, learn from others, or simply meet fellow Chiefs of Staff in the area, this is a great opportunity to plug into the local community. What to expect A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Opportunities to share experiences and insights Food, drinks, and new connections Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape the Chief of Staff community in Chicago this year, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Apr 28

Chief of Staff London Mixer(Apr 28)

We’re excited to bring the Chief of Staff Network (COSN) community together again in London. While we weren’t able to host our last planned gathering on March 18, we’re back and looking forward to reconnecting the community on April 28. A special thank you to Andrea Brewster for generously hosting this mixer and helping foster a vibrant Chief of Staff community in London. Date & Time: April 28, 2026 · 6:00 PM – 8:00 PM GMT Location: Details will be shared with confirmed attendees This informal, in-person mixer is designed to connect Chiefs of Staff and adjacent operators across London for an evening of relaxed conversation, networking, and community-building. Whether you’re already working in a CoS role, supporting senior leadership, or exploring the path, this is a chance to meet others who understand the unique challenges and rewards of the role. There’s no formal agenda — just a brief check-in on COSN and what’s ahead for the London chapter, followed by open networking and candid conversations about operating in and around the Chief of Staff function. What to expect: A casual, welcoming environment Meaningful conversations with fellow CoS and operator professionals Updates on the London chapter and upcoming COSN initiatives New connections and shared experiences Who is this event for? This mixer is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape and strengthen the Chief of Staff community in London, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to secure your spot.

Apr 29

Detroit CoS Meet Up (APR 29)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Detroit for our second gathering of 2026. Building on the momentum from our first meetup this year, we’re continuing to strengthen a connected, high-trust community of Chiefs of Staff and senior operators across Detroit. A special thank you to Lindsey Tocco for generously hosting and supporting the continued growth of the Detroit CoS community. Date & Time: Wednesday, April 29, 2026 · 6:00 PM ET Location: TBD (shared upon confirmation of attendance) This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. As we continue building consistency in Detroit, this meetup is focused on deepening relationships and fostering a committed local network. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Detroit chapter, followed by open networking and shared stories from your experiences supporting founders and senior leadership. What to expect: A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Updates on plans for the Detroit chapter A small, curated group to encourage deeper connection Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in helping shape the next phase of the Chief of Staff community in Detroit, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

May 5

Chief of Staff Launchpad (May-June)

CHIEF OF STAFF LAUNCHPAD A rigorous, cohort-based certification for aspiring and first-time Chiefs of Staff. — Welcome to the Chief of Staff Launchpad, an intensive, cohort-based certification designed to equip aspiring and first-time Chiefs of Staff with the frameworks, skills, and judgment to excel in this high-impact role. This program goes beyond functional expertise. You'll develop the interpersonal, strategic, and organizational fluency required to operate as a trusted partner to your Principal and leadership team. Through 6 live expert-led sessions, structured discussions, and actionable frameworks, you'll learn to navigate the unique dynamics of the Chief of Staff role while leveling up as a strategic leader. — KEY OUTCOMES By the end of this program, you will: Master proven frameworks to navigate the Chief of Staff role with confidence and clarity Strengthen your Principal relationship and build alignment with your leadership team Define your scope and priorities—know what to own, what to delegate, and where to focus your time Build executive presence and expand your influence across the organization Join a lasting community of Chiefs of Staff to share challenges, strategies, and support — COURSE DETAILS Duration: 6 weeks of intensive learning Format: 6 live expert-led sessions, small group discussions, and office hours with former Chiefs of Staff and professional coaches Schedule: Weekly live sessions (Tuesdays, 12pm ET) + Office hours (Wednesdays, 12pm ET) + Welcome and Send-off mixers Certification: Digital certification badge upon completion to showcase on LinkedIn and professional profiles Important: Sessions are conducted live and are not recorded. To receive certification, participants must attend at least 5 of 6 live sessions. Office hours attendance is highly encouraged to maximize your learning and coaching experience. — WHAT'S INCLUDED Expert-led sessions with actionable frameworks tailored specifically for the Chief of Staff role Curated, high-trust cohort and private Slack community for ongoing peer support Structured group coaching through dedicated office hours with experienced Chiefs of Staff and coaches Actionable toolkit you can apply immediately to drive alignment and impact in your role — WHO SHOULD ATTEND Aspiring Chiefs of Staff seeking to build confidence and a clear roadmap before stepping into the role First-time Chiefs of Staff who want to hit the ground running with proven frameworks and community support Operators at early-stage companies looking to structure and elevate their role for greater influence and effectiveness — SCHEDULE & SYLLABUS Cohort 3: May – June 2026 Session 1: CoS Role & Career Path May 5, 12pm ET Welcome Mixer May 6, 12pm ET Session 2: Strategic Planning Fundamentals May 12, 12pm ET Office Hours w/ Aarti Bhatnagar May 13, 12pm ET Session 3: Internal & External Comms May 19, 12pm ET Office Hours w/ Rachel Peck May 20, 12pm ET Session 4: Building an Effective Principal Partnership May 26, 12pm ET Office Hours w/ Scott & Tom May 27, 12pm ET Session 5: Navigating & Aligning the Exec Team Jun 2, 12pm ET Office Hours w/ Juhi Kabra Jun 3, 12pm ET Session 6: Job Search Masterclass Jun 9, 12pm ET Send-off Mixer Jun 10, 12pm ET — ENROLL NOW Visit our website to see all the details about this program. Discounts available for annual CoS Network PRO Members. Contact us for more info.

May 6

Boston CoS Meetup (Wed, 6 May)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Boston for another in-person gathering. A special thank you to Emily Glasgow for generously hosting and helping grow the Chief of Staff community in Boston. Date & Time: May 6, 2026 · 10:30 AM – 12:00 PM ET Location: Shared upon confirmation of attendance This informal, in-person meetup will bring together Chiefs of Staff and adjacent operators across Boston for thoughtful conversation, meaningful connections, and shared insights into the realities of operating in strategic leadership roles. Designed as a focused morning gathering, this session will provide space for Chiefs of Staff and operators to exchange perspectives, discuss common challenges, and learn from peers navigating similar responsibilities within their organizations. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Boston community, followed by open discussion and networking with fellow operators. What to expect A welcoming, conversational environment Meaningful discussions with fellow Chiefs of Staff and operators Peer insights and shared experiences A small, curated group to encourage thoughtful participation Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in connecting with peers and helping grow the Chief of Staff community in Boston, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

May 7

Berlin Chief of Staff Meetup (May 7)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Berlin for our next in-person gathering. Building on the momentum from previous meetups, this event will continue strengthening a high-trust community of Chiefs of Staff and senior operators across Berlin. A special thank you to Ania Montoya for hosting and helping lead the Berlin Chief of Staff community. Date & Time: May 7, 2026 · 6:00 PM CET Location: Shared upon confirmation of attendance This informal, in-person meetup will bring together Chiefs of Staff and adjacent operators for meaningful conversation, peer connection, and shared insights into the realities of operating in strategic leadership roles. In addition to open networking, the evening will include a short panel or fireside-style conversation, creating space to explore real experiences, practical lessons, and challenges faced in the CoS role. There’s no rigid agenda — just a brief touchpoint on COSN and what’s ahead for the Berlin chapter, followed by a mix of discussion, networking, and shared stories from operators supporting founders and leadership teams. What to expect A casual, welcoming environment A short panel or fireside conversation with experienced operators Meaningful discussions with fellow Chiefs of Staff and operators Opportunities to exchange insights, challenges, and lessons learned Food, drinks, and new connections Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re interested in connecting with peers and helping grow the Chief of Staff community in Berlin, we’d love to have you join us. Attendance will be capped to keep the group intimate — please RSVP to save your spot. For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit: https://www.chiefofstaff.network/

Nov 20

Chief of Staff Connect - London

Chief of Staff Connect New York 2026 Date: November, 2026 (Final Date TBA) Location: London, UK (Venue TBA) From Force Multiplier to Builder Chief of Staff Connect is returning to London in 2026, bringing together senior Chiefs of Staff who are building the next generation of company execution. Join us for a 1-day gathering designed for leaders who don't just support strategy, but turn it into measurable outcomes. This year's focus is From Force Multiplier to Builder: the shift from amplifying leaders behind the scenes to owning the systems, programs, and operating models that move the business forward. We'll spotlight Chiefs of Staff delivering real results (revenue growth, cost savings, and organizational efficiency) while strengthening the power skills and judgment required to lead through complexity. Core Themes Architecting Systems That Scale: From Ad Hoc to Operating Model Design repeatable operating systems for planning, decisions, and communication that reduce friction and enable growth without constant intervention. The Launcher's Toolkit: Shipping Projects That Move Metrics Learn how top CoS leaders scope, resource, and deliver high-impact initiatives with clear KPIs, from AI implementations to new business units. Developing Leaders, Not Just Supporting Them Design programs that grow your executive team's capabilities and create succession depth across the organization. Engineering Intelligent Operations: The CoS as Chief AI Architect Take ownership of AI strategy execution—evaluating tools, designing workflows, driving adoption, and establishing governance that turns AI from experiment to competitive advantage. From Firefighter to Architect: Designing Organizational Resilience Stop solving the same problems repeatedly. Create early warning systems, decision protocols, and cross-functional structures that prevent crises and accelerate recovery. Who Should Attend This event is built for senior Chiefs of Staff who are ready to move beyond execution support and become the architects of how their companies operate. If you're driving strategic initiatives, building organizational systems, or leading transformation, this is your peer group. Combine Your Ticket with PRO+ Membership Save up to 24% when you bundle your Chief of Staff Connect ticket with an annual Chief of Staff Network PRO+ membership. Get year-round access to our private community of 900+ Chiefs of Staff, exclusive training programs, monthly events, and the peer network that will help you continue building long after the conference ends. Apply to join PRO Memberships →

Oct 22

Chief of Staff Connect - New York

Jul 14

Chief of Staff Launchpad (July - August)

CHIEF OF STAFF LAUNCHPAD A rigorous, cohort-based certification for aspiring and first-time Chiefs of Staff. — Welcome to the Chief of Staff Launchpad, an intensive, cohort-based certification designed to equip aspiring and first-time Chiefs of Staff with the frameworks, skills, and judgment to excel in this high-impact role. This program goes beyond functional expertise. You'll develop the interpersonal, strategic, and organizational fluency required to operate as a trusted partner to your Principal and leadership team. Through 6 live expert-led sessions, structured discussions, and actionable frameworks, you'll learn to navigate the unique dynamics of the Chief of Staff role while leveling up as a strategic leader. — KEY OUTCOMES By the end of this program, you will: Master proven frameworks to navigate the Chief of Staff role with confidence and clarity Strengthen your Principal relationship and build alignment with your leadership team Define your scope and priorities—know what to own, what to delegate, and where to focus your time Build executive presence and expand your influence across the organization Join a lasting community of Chiefs of Staff to share challenges, strategies, and support — COURSE DETAILS Duration: 6 weeks of intensive learning Format: 6 live expert-led sessions, small group discussions, and office hours with former Chiefs of Staff and professional coaches Schedule: Weekly live sessions (Tuesdays, 12pm ET) + Office hours (Wednesdays, 12pm ET) + Welcome and Send-off mixers Certification: Digital certification badge upon completion to showcase on LinkedIn and professional profiles Important: Sessions are conducted live and are not recorded. To receive certification, participants must attend at least 5 of 6 live sessions. Office hours attendance is highly encouraged to maximize your learning and coaching experience. — WHAT'S INCLUDED Expert-led sessions with actionable frameworks tailored specifically for the Chief of Staff role Curated, high-trust cohort and private Slack community for ongoing peer support Structured group coaching through dedicated office hours with experienced Chiefs of Staff and coaches Actionable toolkit you can apply immediately to drive alignment and impact in your role — WHO SHOULD ATTEND Aspiring Chiefs of Staff seeking to build confidence and a clear roadmap before stepping into the role First-time Chiefs of Staff who want to hit the ground running with proven frameworks and community support Operators at early-stage companies looking to structure and elevate their role for greater influence and effectiveness — SCHEDULE & SYLLABUS Session 1: CoS Role & Career Path Jul 14, 12pm ET Welcome Mixer Jul 15, 12pm ET Session 2: Strategic Planning Fundamentals Jul 21, 12pm ET Office Hours w/ Aarti Bhatnagar Jul 22, 12pm ET Session 3: Internal & External Comms Jul 28, 12pm ET Office Hours w/ Rachel Peck Jul 29, 12pm ET Session 4: Building an Effective Principal Partnership Aug 4, 12pm ET Office Hours w/ Scott & Tom Aug 5, 12pm ET Session 5: Navigating & Aligning the Exec Team Aug 11, 12pm ET Office Hours w/ Juhi Kabra Aug 12, 12pm ET Session 6: Job Search Masterclass Aug 18, 12pm ET Send-off Mixer Aug 19, 12pm ET — ENROLL NOW Visit our website to see all the details about this program. Discounts available for annual CoS Network PRO Members. Contact us for more info.

May 19

AI & The Law: Know Enough to Be Dangerous

AI & the Law: Know Enough to Be Dangerous AI is reshaping how organizations operate and most leaders are navigating it without a map. This three-session live course equips Chiefs of Staff, Legal Ops professionals, and business operators with the strategic and legal fluency they need to guide their organizations confidently. By the end, you'll know the right questions to ask, the red flags to watch for, and how to become the most informed person in the room when AI decisions are on the table. This course is a collaboration between Operators (Chief of Staff Network, Legal Operators, BizOps Network) and Briefly (www.brieflynow.com). Session 1: Tuesday, May 19 at 12pm ET AI Risk vs. Reward: Building Your Organization's Adoption Strategy Speaker: Damien Riehl, Clio Your CEO wants to move fast on AI. Your legal team wants to pump the brakes. Your job is somewhere in between. In this kickoff session, Damien Riehl, lawyer, engineer, and one of the most in-demand AI speakers in the legal world, cuts through the noise to give you a clear-eyed framework for thinking about AI adoption. From risk-tolerant tech startups to compliance-heavy healthcare systems, every organization faces the same fundamental tension. This session gives you language, scenarios, and strategies to navigate it — and to help your leadership team make smarter decisions faster. You'll come away able to: Articulate the real risks and rewards of AI adoption in plain language Advise your C-suite on balancing speed with compliance Understand how different organizational cultures require different AI strategies Speak confidently about legal tech capabilities and what's actually possible Session 2: Thursday, May 21 at 12pm ET AI Governance Crash Course: What the Law Actually Says Right Now Speaker: Shannon Yavorsky (primary) / Julia Apostle (EU AI Act specialist), Orrick There's no single AI law - and that's exactly what makes this complicated. The EU AI Act is coming into force. Hundreds of state bills are actively being debated in the U.S., and in the meantime, existing laws like GDPR, CCPA, Title VII, the FTC Act, and huge numbers of state laws are already being applied to AI in ways most leaders don't realize. This session is a practitioner's guide to the current state of AI governance. We’ll cover what’s in force now, what's coming down the pipeline, and critically, what your organization probably needs to be doing right now that it isn't. You'll come away able to: Understand which existing laws govern AI use at your organization today Give a confident 10-minute briefing to your exec team on the regulatory landscape Understand the basics of AI risk categories under the EU AI Act and how they may or may not apply to your company Identify the highest-risk areas in your organization Track what to watch for as federal and state legislation continues to evolve Session 3: Tuesday, May 26 at 12pm ET AI Contracting: Protecting Your Organization in Every Deal Speaker: David Tollen, Tech Contracts Academy & Sycamore Law Group Most AI law is happening in contracts, not in legislatures. Whether you're buying AI tools, selling AI-powered products, or managing a vendor relationship that predates the AI era, the terms of your agreements matter more than ever. Data privacy clauses, indemnity provisions, and DPAs that seemed routine two years ago now carry entirely different weight. In this practical closing session, David Tollen, one of the country's leading experts on technology contracts, walks through what non-lawyers need to know to negotiate smarter, avoid costly mistakes, and work effectively alongside their legal and commercial teams. You'll come away able to: Identify the key provisions in AI-related contracts that require extra scrutiny Understand what questions to ask before signing any AI vendor agreement Know when to revisit existing contracts in light of AI developments Work more effectively with your commercial lawyers and revenue teams Bonus: Office Hours Session Following the three core sessions, an optional open-format office hours will be available for registered attendees. No formal teaching, just open Q&A and peer conversation moderated by Adam Stofsky (Briefly) and the Sylva team. It will be a space to connect, share real situations, and get perspectives from others navigating the same challenges.

May 15

Chief of Staff Connect - San Francisco

May 13

CoS San Diego Meetup ( May 13)

We’re excited to bring the Chief of Staff Network (COSN) community back together in San Diego for our Q2 gathering. A special thank you to Mary Hendra for continuing to host and thoughtfully shape the San Diego CoS community. Date & Time: Wednesday, May 13, 2026 · 5:00 PM PT Location: TBD (shared upon confirmation of attendance) This informal, in-person meetup will bring together Chiefs of Staff and adjacent operators across San Diego for meaningful conversation, shared learning, and genuine connection. Based on recent discussions and past gatherings, a few themes continue to surface: The many hats we wear as Chiefs of Staff Practical strategies for juggling competing priorities Transitions, clarity of role, and managing up effectively Where the CoS seat can lead next Rather than a rigid agenda, this will be a facilitated, conversational gathering shaped by the lived experiences in the room. Expect candid dialogue, practical insights, and space to explore what “next” looks like in your own journey. What to expect: A welcoming, high-trust environment Candid discussion around real CoS challenges Peer insights and shared frameworks Meaningful connections with fellow Chiefs of Staff and operators Who is this event for? This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles. Please include your current job title and company so we can verify your role and approve your registration. If you’re navigating the complexity of the CoS role — or thinking intentionally about where it leads — we’d love to have you join us. Attendance will be capped to keep the group intimate and discussion-rich — please RSVP to save your spot. For more information about the Chief of Staff Network and upcoming events, programs, and conferences, visit: https://www.chiefofstaff.network/

May 7

Chief of Staff Connect New York

What Our Chapter Leaders Say

Chapter Events

Paris CoS Meetup (Apr 14)

Leadership at Human Speed: A Workshop for Chiefs of Staff

Austin CoS Happy Hour (4/21)

Dallas Chief of Staff Meetup (Tue Apr 21)

Chicago Chief of Staff Meetup (Wed Apr 22)