Ask a Chief of Staff

📣 Calling all NYC based Chiefs of Staff! We have 3️⃣ great events coming up at the end of April and we'd love to see you there ⬇️ ➕ a secret bonus event that's invite only....so DM me if you want know more 💌 1️⃣ 𝗣𝗲𝗼𝗽𝗹𝗲 𝗟𝗲𝗮𝗱𝗲𝗿𝘀 𝗖𝗼𝗳𝗳𝗲𝗲 𝗠𝗲𝗲𝘁𝘂𝗽 𝗵𝗼𝘀𝘁𝗲𝗱 𝗯𝘆 Offsite 𝗮𝗻𝗱 Ask a Chief of Staff Tuesday, April 22, 8AM - 930AM ☕️ Come grab a cup of coffee/tea on us before you head off for your work day! 2️⃣ 𝗖𝗼𝗳𝗳𝗲𝗲 𝗮𝗻𝗱 𝗖𝗼-𝗪𝗼𝗿𝗸𝗶𝗻𝗴 𝗶𝗻 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝘄𝗶𝘁𝗵 Industrious Thursday, April 24, 10AM - 5PM 🍕Come and co-work with fellow Chiefs of Staff - breakfast and lunch will be served! 3️⃣ 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝗛𝗮𝗽𝗽𝘆 𝗛𝗼𝘂𝗿 𝗶𝗻 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝘄𝗶𝘁𝗵 Notion Tuesday, April 29, 6-8PM 🍹 Have a drink on a beautiful (covered) rooftop and connect with Chiefs of Staff from all over the city! ⬇️ Links to register for all events in the comments below ⬇️

📣 Looking for a Chief of Staff role? Or want to make sure your resume is interview-ready? Join us on April 1️⃣ 0️⃣  for a Peer Resume Review, led by our incredible community mentor, Sam Chai (former Chief of Staff at listen.dev and Recruiting Lead at Hypercare)! Whether you’re actively exploring new roles or simply staying sharp, this session will walk you through how to: ✅ Highlight what matters most in your Chief of Staff experience ✅ Tailor your resume to different industries and company sizes ✅ Avoid the most common resume pitfalls 🗓 Thursday, April 10 | 1:00–2:15PM ET 🔗 Register here: https://lu.ma/axnf40b3 Want 💲🔟 off your registration fee? Drop a 🤑 in the comments and I'll DM you a code! Bring your resume and leave with feedback, fresh ideas, and more clarity on your next move. Hope to see you there! 💼💫

Happy Monday! 👋🏼 If you're on the market for a new Chief of Staff role, you're in luck! Ask a Chief of Staff is hiring for 🔟 ➕ roles all over the US. Interested in any of these roles? Go to bit.ly/AaCoS-open-roles to apply! 💼 𝗨𝗦 𝗙𝗼𝘂𝗻𝗱𝗶𝗻𝗴 𝗣𝗮𝗿𝘁𝗻𝗲𝗿 𝘁𝗼 𝗮 𝗚𝗹𝗼𝗯𝗮𝗹 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹 𝗔𝗱𝘃𝗶𝘀𝗼𝗿𝘆 𝗙𝗶𝗿𝗺 (𝗦𝗙, 𝗟𝗔, 𝗼𝗿 𝗡𝗬𝗖) - Remote (SF, LA or NYC) - 8-12+ years of overall experience - Experience in MBB or top-tier strategy consulting environment - Relationship-first mindset with high EQ, discretion, and polished interpersonal skills - Comfortable operating without rigid structures — this is a role for someone who thrives in ambiguity and is excited to build from scratch. - An entrepreneurial builder – ideally a founder, operator, or someone who’s helped stand up a new initiative 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $200K-$300K + bonus + equity 🤖 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗖𝗼-𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝗮𝘁 𝗮𝗻 𝗔𝗜 𝗣𝗹𝗮𝘁𝗳𝗼𝗿𝗺 𝗦𝘁𝗮𝗿𝘁𝘂𝗽 - SF in person - 5-7 years of overall experience - Experience in early stage startups/high-growth environments, ideally with exposure to the AI product space - Must have hands-on experience in financial modeling, business planning, budgeting, and data analysis - Proven track record in leading cross-functional initiatives and streamlining operations, with the ability to handle both strategic initiatives and day-to-day operations 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $150K-$165K + equity  𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗠𝗮𝗻𝗮𝗴𝗶𝗻𝗴 𝗣𝗮𝗿𝘁𝗻𝗲𝗿 𝗼𝗳 𝗮 𝗩𝗖 𝗙𝗶𝗿𝗺 - SF in person - 5-7 years of overall experience - Strong operational background in venture capital or VC-backed companies - Proven track record managing follow-up and administrative tasks, ensuring priorities are met and nothing falls through the cracks - Oversee special projects like website redesigns and portfolio company platform work - Ability to manage projects independently and work with senior executives 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $150K–$160K + carry 🏛️ 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗖𝗼-𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝗼𝗳 𝗮𝗻 𝗔𝗜 𝗣𝗼𝗹𝗶𝗰𝘆 𝗡𝗼𝗻 𝗣𝗿𝗼𝗳𝗶𝘁 (𝗦𝗙 𝗼𝗿 𝗗𝗖) - Hybrid in SF or DC - 7+ years of experience - Experience in strategic roles, with client-facing experience at top consulting firms is a plus - Knowledge and experience in AI governance, technology policy, or related fields preferred - Proven track record in driving outcomes through process optimization, strategic planning, and cross-functional collaboration - Exceptional executive support and communication skills, with the gravitas to “manage up” and stand in for senior executives in key meetings - Data-driven decision maker experienced with OKRs and synthesizing complex information to inform strategy 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $150K-$180K + benefits

Thank you for the warm welcome, Austin! 🤠 🍻 Last night, Ask a Chief of Staff hosted it's first ever Chief of Staff Happy Hour in Austin and brought together Chiefs of Staff from all stages and sizes of companies 🍺 It was so great to see the Chief of Staff community come together, despite the rain and traffic, and we can't wait to be back to do it again soon!

We're hiring for 🔟➕ Chief of Staff roles at Ask a Chief of Staff and are looking for amazing candidates to fill these positions! ➡️ Interested in any of these roles? Apply at bit[.]ly/AaCoS-open-roles 💻 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗖𝗼-𝗳𝗼𝘂𝗻𝗱𝗲𝗿𝘀 𝗮𝘁 𝗮𝗻 𝗔𝗜 𝗣𝗹𝗮𝘁𝗳𝗼𝗿𝗺 𝗦𝘁𝗮𝗿𝘁𝘂𝗽 (𝗦𝗙 𝗶𝗻 𝗽𝗲𝗿𝘀𝗼𝗻) - 5-7 years of overall experience - Experience in early stage startups/high-growth environments, ideally with exposure to the AI product space - Must have hands-on experience in financial modeling, business planning, budgeting, and data analysis - Proven track record in leading cross-functional initiatives and streamlining operations, with the ability to handle both strategic initiatives and day-to-day operations 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $150K-$165K + equity 💼  𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗠𝗮𝗻𝗮𝗴𝗶𝗻𝗴 𝗣𝗮𝗿𝘁𝗻𝗲𝗿 𝗼𝗳 𝗮 𝗩𝗖 𝗙𝗶𝗿𝗺 (𝗦𝗙 𝗶𝗻 𝗽𝗲𝗿𝘀𝗼𝗻) - 5-7 years of overall experience - Strong operational background in venture capital or VC-backed companies - Proven track record managing follow-up and administrative tasks, ensuring priorities are met and nothing falls through the cracks - Oversee special projects like website redesigns and portfolio company platform work - Ability to manage projects independently and work with senior executives - Not looking for someone pursuing an investment track 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $150K–$160K + potential carry 🐶 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 𝘁𝗼 𝘁𝗵𝗲 𝗖𝗢𝗢 𝗮𝘁 𝗮 𝗣𝗲𝘁 𝗛𝗲𝗮𝗹𝘁𝗵 𝗦𝘁𝗮𝗿𝘁𝘂𝗽 (𝗡𝗬𝗖 𝗛𝘆𝗯𝗿𝗶𝗱) - 5–8+ years of overall experience - Experience in strategy, operations, consulting, or a Chief of Staff role; high-growth startup and B2B SaaS experience preferred - Own the company-wide OKR process, driving strategic planning and alignment - Demonstrated success in streamlining workflows, enhancing cross-functional collaboration, and creating scalable communication frameworks - Track record of leveraging data-driven insights and managing dashboards to provide real-time visibility into business performance 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $140K-$160K + benefits 🩺 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗠𝗮𝗻𝗮𝗴𝗲𝗿 𝗮𝘁 𝗮𝗻 𝗔𝗜 𝗣𝗼𝘄𝗲𝗿𝗲𝗱 𝗣𝗮𝘁𝗶𝗲𝗻𝘁 𝗖𝗮𝗿𝗲 𝗣𝗹𝗮𝘁𝗳𝗼𝗿𝗺 (𝗥𝗲𝗺𝗼𝘁𝗲 𝗨𝗦) - Northeast DC/NY preferred - 5+ years in account management, customer service, operations, or sales in value-based healthcare and Risk Adjustment - Must have hands-on experience with Risk Adjustment and Quality operations (EDPS, in-home assessments, chart retrieval, HEDIS) - Proven ability to drive customer value through cost reduction, revenue growth, and improved outcomes - Skilled in coordinating with internal teams and vendors for seamless service delivery and renewals 𝗧𝗮𝗿𝗴𝗲𝘁 𝗦𝗮𝗹𝗮𝗿𝘆: $120K-$150K + equity

🙇🏻♀️ I don’t often share too much about my entrepreneurial journey: mostly because I’m still figuring it out along the way. But when Dreamers & Doers® and Women On Topp gave me an opportunity to reflect on my first year as a founder, it gave me a chance to pause and look back 💜 👀 It’s easy to look back and say “I should’ve done X differently.” But when you’re in it—building something from scratch—it’s all trial, error, and gut instinct. In those early days of Ask a Chief of Staff, I was focused on quick wins: close a deal, generate revenue, prove that this idea had legs. But I quickly learned that the real challenge wasn’t starting: 𝗶𝘁 𝘄𝗮𝘀 𝘀𝘂𝘀𝘁𝗮𝗶𝗻𝗶𝗻𝗴. 💡If I could go back, I’d remind myself: 𝗟𝗼𝗻𝗴-𝘁𝗲𝗿𝗺 𝘀𝘂𝗰𝗰𝗲𝘀𝘀 𝗰𝗼𝗺𝗲𝘀 𝗳𝗿𝗼𝗺 𝗯𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝘀𝘁𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗶𝗻 𝗺𝗶𝗻𝗱. Grateful to be featured alongside 1️⃣ 3️⃣ incredible women in this new piece from Women On Topp, reflecting on the messy, powerful, human side of year 1️⃣ entrepreneurship. ⬇️ Full article in the comments below ⬇️ Thank you to Dreamers & Doers® & Doers for always amplifying women’s voices and for curating such an inspiring group of founders to learn from 💜

👀 Chiefs of Staff: Let’s talk about the stuff no one else is saying out loud. I’m teaming up with Maggie Olson of Nova Chief of Staff for a no-fluff, no-filter conversation on the 𝗵𝗼𝘁 𝘁𝗮𝗸𝗲𝘀 that are shaking up the Chief of Staff world. 🚨 Should a Chief of Staff always be “on”? 🚨 Does being a former EA help or hurt? 🚨 What red flags should you actually watch for in a CoS role? 🚨 Will AI replace the Chief of Staff role? 🚨 And… is the Chief of Staff title losing its meaning? Whether you’re a current Chief of Staff, aspiring one, or a CEO hiring for the role, this is the conversation you want in your calendar ⬇️ 🗓 April 10, 1-2pm ET 📍Free live webinar + Q&A 🔗 Register here: https://lu.ma/veyhunfi Hope to see you there!

Ask a Chief of Staff is coming to Austin!! 🎉 On March 2️⃣ 7️⃣ th, we’re hosting our first-ever Austin Chief of Staff Happy Hour at Zilker Brewing Company 🍻 Attendees will have a chance to: 🔹 Meet fellow Chiefs of Staff 🔹 Swap stories & best practices 🔹 Build connections in a room full of people who get it Whether you’re new to the role or a seasoned Chief of STaff, this is your chance to unwind, network, and celebrate the unique impact of the Chief of Staff position. ⏰ March 2️⃣ 7️⃣ | 6:00 - 8:00 PM CDT 📍 Zilker Brewing Company, Austin, TX Space is limited, so register now to save your spot! ⬇️ https://lu.ma/i8gl59f7 Tag an Austin based Chief of Staff who should join us! 👇

For Chiefs of Staff, AI has the potential to streamline operations, cut through the noise, and help you focus on what really moves the needle. But with so many options out there, how do you know what actually works? 🗓 Join us on 𝗠𝗮𝗿𝗰𝗵 2️⃣ 8️⃣ 𝘁𝗵 for another workshop co-hosted by Ask a Chief of Staff and Ambient: 🤖 𝗔𝗜 𝗶𝗻 𝗔𝗰𝘁𝗶𝗼𝗻: 𝗔𝗜 𝗧𝗼𝗼𝗹𝘀 𝗧𝗵𝗮𝘁 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗛𝗲𝗹𝗽 𝗖𝗵𝗶𝗲𝗳𝘀 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳 Our last AI workshop had over 7️⃣ 0️⃣ 0️⃣ registrants—and we’re back with another free session that’s open to the public! 𝗪𝗵𝗮𝘁 𝘁𝗼 𝗲𝘅𝗽𝗲𝗰𝘁: ✅ Live AI tool demos—real-world examples, not just theory ✅ A hands-on session—build your first AI-powered app (no coding required!) ✅ Q&A session—get your AI questions answered in real time 𝗜𝗳 𝘆𝗼𝘂’𝗿𝗲: ⚡ Drowning in meetings & emails and want AI to do the heavy lifting ⚡ Unsure which AI tools are actually worth using ⚡ Curious how Chiefs of Staff are leveraging AI in their daily workflows This workshop is for you. 5️⃣ 0️⃣ 0️⃣  seats only — grab your spot now! 🎟 ➡️ Link to register: https://lu.ma/vavg6mut ⬅️