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.

Chief of Staff Connect SF - ReConnect

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/

Chief of Staff San FranciscoPost Connect Meetup

We’re excited to bring the Chief of Staff Network (COSN) community together in San Francisco for a special post-Connect meetup following the Chief of Staff Connect Summit in SF on May 15, 2026. This gathering is designed as a more relaxed follow-up for attendees, speakers, and members of the broader Bay Area CoS community to continue conversations, deepen relationships, and reconnect after the summit. A special thank you to Melinda Munroe, Reuben Torenberg, and the CBRE team for hosting this gathering at Salesforce Tower. Date & Time: June 9, 2026 · 6:00 PM – 8:30 PM PT Location: Salesforce Tower (shared upon confirmation of attendance) After a full day of ideas, conversations, and new connections at CoS Connect SF, this meetup creates space to continue those discussions in a more informal setting alongside fellow Chiefs of Staff and operators. Whether you attended the summit or are joining the broader San Francisco CoS community for the first time, this evening is designed to help operators connect more deeply with peers navigating similar leadership challenges and opportunities. There’s no formal agenda — just good conversations, shared experiences, and the opportunity to build stronger relationships within the Chief of Staff community. What to expect A relaxed, high-quality networking environment Continued conversations from CoS Connect SF Meaningful connections with Chiefs of Staff and senior operators Drinks, conversations, and new introductions 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 attended CoS Connect SF, we’d especially love to see you continue the conversations here. Attendance will be capped to keep the group thoughtful and high-quality — 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/

Melbourne Chief of Staff Network Chapter Launch

We’re excited to officially launch the Chief of Staff Network (COSN) community in Melbourne. This marks our first COSN gathering in Melbourne, bringing together Chiefs of Staff and senior operators across the city to start building a strong, connected local community. A special thank you to Zoe Zropf for hosting and supporting the launch of the Melbourne chapter. Date & Time: June 10, 2026 · 6:00 PM AEST Location: Shared upon confirmation of attendance This informal, in-person gathering is designed to bring together Chiefs of Staff and adjacent operators across Melbourne 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 Melbourne. 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 Melbourne, 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 Melbourne 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 Melbourne, 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/

Workflow Thinking: The Skill Behind Every Automation

The leaders getting the most out of AI aren't just better at prompting. They think differently about their work—seeing tasks as part of flows rather than isolated actions. That shift is what separates someone who uses AI one task at a time from someone who builds systems that run without them. This session gives you the mental model behind tools like Zapier, Google Flows, and Claude Cowork—and the discipline of mapping processes before touching any software. What You'll Take Away A reusable lens for spotting which of your workflows are automation-ready. The data mapping step most leaders skip—and why it breaks everything downstream. Enough fluency to design, evaluate, and direct cross-app workflows without writing code. 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.

Chief of Staff Connect - Berlin Forum

Chief of Staff Connect Berlin Forum - 2026 Date: July 2, 2026 Location: Kreuzberg, Berlin From Force Multiplier to Builder Chief of Staff Connect is coming to Berlin 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.

Sydney CoS Meetup (7/9)

We’re excited to bring the Chief of Staff Network (COSN) community back together in Sydney for our second meetup of 2026. Following a strong launch earlier this year, we’re continuing to build momentum and strengthen connections among Chiefs of Staff and senior operators across Sydney and the broader Australia community. A special thank you to Zoe Zropf for hosting and continuing to lead the growth of the Sydney Chief of Staff community. Date & Time: July 9, 2026 · 6:00 PM AEST Location: Shared upon confirmation of attendance This informal, in-person meetup is designed to bring together Chiefs of Staff and adjacent operators for an evening of relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles. Whether you’re currently in the CoS seat, supporting founders and executive teams, or navigating broader operational leadership responsibilities, this is an opportunity to connect with peers who understand the unique challenges and opportunities of the role. There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Sydney chapter, followed by open networking and shared conversations with fellow operators. What to expect A casual, welcoming environment Meaningful conversations with fellow Chiefs of Staff and operators Opportunities to exchange ideas, challenges, and lessons learned 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 Sydney and across Australia, 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/