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.

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/

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/

The CoS AI Build-A-Thon

You’ve seen the magic in Part 1: Claude Cowork, where we oriented you to the latest AI capabilities. Now, it’s time for Part 2: The Build-A-Thon, where we move from "chatting" to constructing durable systems. This 90-minute intensive is designed for the Chief of Staff who is tired of being the bottleneck for communications and internal operations. You will build prescriptive Claude Projects, custom Skills, and interactive Artifacts  that turn "internal friction" into "operational flow." No coding required—just your operational expertise and a bias for action. By registering for this event, you agree that your contact information may be shared with event sponsors and partners for follow-up communications related to this session.

Amsterdam CoS Borrel (May 13)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Amsterdam for our second meetup of 2026. Building on the momentum from our first gathering this year, this borrel is all about continuing to strengthen connections within the local CoS community — while also creating space for more practical, behind-the-scenes sharing. A special thank you to Trudy Westby for generously hosting and supporting the Amsterdam Chief of Staff community. Date & Time: May 14, 2026 · 6:30 PM CET Location: Shared upon confirmation of attendance This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators for an evening of relaxed conversation, meaningful connections, and practical insights. Alongside open networking, we’ll introduce a light “show & tell” format, where a few attendees will walk through real examples from their day-to-day work — the systems, templates, and processes that quietly keep their organizations running. Think of it as a peek behind the curtain into how Chiefs of Staff actually operate. You might hear things like: How someone structures their weekly CEO brief and why A practical approach to running OKRs or leadership reviews A system or workflow that’s made a meaningful impact The goal is to keep things grounded, practical, and useful — with plenty of room for discussion, questions, and shared learning. What to expect A casual, welcoming borrel environment Short, practical “show & tell” moments from fellow Chiefs of Staff Meaningful conversations and peer exchange New connections within the Amsterdam 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 peers and learning how others are solving real operational challenges, 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/

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/

Chief of Staff Connect - San Francisco

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.

Building an AI Champions Program That Actually Works

Most AI Champions programs start strong and end with a Slack channel no one checks. Without a defined role and real accountability, it becomes a volunteer project - the first thing dropped when priorities shift. And even when programs survive, a second failure mode kicks in: ideas outpace execution. No one has the skills to build the agent, ship the workflow, or turn the opportunity into a working solution. The organizations pulling ahead are developing people who can execute, not just advocate. This session covers what that requires: the right champions, the right skill-building path, and the right measures to keep it alive. What You'll Take Away A clear profile for identifying champions who drive execution. The technical and business skill mix that turns good ideas into working solutions. KPIs that connect the program to business outcomes past the pilot. By registering for this event, you agree that your contact information may be shared with event sponsors and partners for follow-up communications related to this session.

Zurich Chief of Staff Chapter Launch

We’re excited to officially launch the Chief of Staff Network (COSN) community in Zurich. This marks our first COSN gathering in Zurich, bringing together Chiefs of Staff and senior operators across the city to start building a strong, connected local community. A special thank you to Noah Dwora for hosting and helping kick off the Zurich chapter. Date & Time: June 4, 2026 · 6:00 PM CET Location: Shared upon confirmation of attendance This informal, in-person gathering will bring together Chiefs of Staff and adjacent operators for a relaxed evening of conversation, connection, and community-building. Whether you’re currently in a CoS role, working closely with founders or executive teams, or exploring the path, this is an opportunity to meet peers who understand the unique nature of the role — and to help shape what the Chief of Staff community looks like in Zurich. There’s no formal agenda — just a light introduction to the Chief of Staff Network, followed by open networking and candid conversations about operating in (and alongside) the Chief of Staff role. As this is our first meetup in Zurich, the focus is simple: bring together great operators, start meaningful conversations, and lay the foundation for a strong local network. What to expect A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators An introduction to COSN and plans for the Zurich chapter Drinks, conversations, and new connections Who is this event for? This event 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 Zurich, we’d love to have you join us. Spaces are limited 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/