Meet Clara Ma, the Founder and CEO of Ask a Chief of Staff, a resource for Chiefs of Staff looking to secure high-impact roles and drive results within their respective companies.
Clara’s entrepreneurial journey began with her own experience as a Chief of Staff in early 2020. Facing the challenge of navigating a new role with little direction, she reached out to other Chiefs of Staff for support and quickly saw the need to share the knowledge she was gaining. This ultimately led to the creation of Ask a Chief of Staff, which was designed to help new and experienced Chiefs of Staff navigate their roles through workshops, mentorship, networking, and personalized coaching services. Today, Clara and her company are continuing their mission of building a collaborative and supportive environment where their members can help one another succeed as Chiefs of Staff.
We asked Clara about the founding story behind Ask a Chief of Staff, if she always knew she wanted to be an entrepreneur, and what’s next for her and her company.
Tell us the story behind your company’s founding. How and why did you start working on Ask a Chief of Staff?
My journey as an entrepreneur into the executive search and talent sector began with my own career experience. I took on a Chief of Staff (CoS) position in February 2020. I had never previously served in the role and I was supporting a CEO who had never had a Chief of Staff. The CoS role was an emerging feature of the startup ecosystem at that time. Therefore, my executive principal and I didn’t have much to rely on when it came to defining what a successful CoS/CEO dynamic looked like. I found myself reaching out to other Chiefs of Staff on LinkedIn, sending cold introductions asking for 15 minutes, or buying virtual coffees so I could benchmark myself against a new set of peers.
After starting to find the rhythm, I saw a unique opportunity to build scalable mechanisms for this otherwise disaggregated knowledge. I put together my experience of relying on a networked community as a career accelerator with the opportunity to build a shared well of knowledge around the role, and Ask A Chief of Staff was born.
What problem does Ask a Chief of Staff solve?
Ask a Chief of Staff (AaCoS) delivers uniquely integrated community, knowledge, and coaching as the premier resource for Chiefs of Staff who aim to secure high-impact roles and drive results. Data gathered from my members shows that many of them are joining the AaCoS Community upon entering their Chief of Staff roles for the first time. Along with this data, new Chiefs of Staff consistently share that they are expected to “show up and figure it out” with very little direction on where to even start. And for experienced Chiefs of Staff, novel problems consistently emerge. There is a lack of accessible and credible knowledge for this role because of its recent integration into the corporate space, especially in the fast-paced, venture-backed ecosystem. This was a challenge I faced when serving as CoS at an early-stage startup. When members join the AaCoS Community, they gain access to recurring online workshops taught by industry leaders, a mentorship directory of vetted former Chiefs of Staff, a network of similarly ambitious CoS peers, and personalized job search and coaching services.
Did you always know that you wanted to be an entrepreneur?
Despite having grown up in Silicon Valley and attending nearby UC Berkeley for my undergraduate studies where being a founder was a common aspiration, I didn't envision a career as an entrepreneur. I launched my career in technology recruiting. Through various roles within startups, I gained a deep understanding of the tech industry's dynamics. I stumbled into entrepreneurship after a period of burnout and a reflective sabbatical at my last corporate role.
My decision to travel this new career path was driven by my opportunistic desire to serve an overlooked niche that I saw in my work as a tech recruiter: enhancing the performance of startups and their executives by placing Chiefs of Staff. I recognized a talent market gap that matched my skills and experience, and I seized on an ideal moment to incorporate a business. My entrepreneurial journey is more about solving a specific problem—one that I had faced myself—than it is about adopting an entrepreneurial identity as a founder. My journey highlights the fact that entrepreneurship can stem from practical considerations applied to opportunities to leverage one’s skills where they are needed most.
What were the most difficult and most impactful lessons you’ve learned starting and running a company?
The importance of adaptability and community building in a niche market. Before launching, I hadn’t fully appreciated the seasonal nature of the recruiting industry, which created significant fluctuations in the first few months of my business. This stark realization came after the initial excitement of my first job placement through my fledgling company, soon followed by the onset of a low season. The highs and lows were intense, but this challenge also presented an opportunity to diversify and stabilize the business.
The development of a community around the Chief of Staff role, supported by my steady delivery of tailored content, attracted professionals seeking career advancement for my talent pipeline. Building out a new community-based business segment also created a more reliable revenue stream, as members subscribed and syndicated the value of being connected to their peers. This supplemental focus on community building helped mitigate the seasonal dips in recruiting revenue. It also provided constant engagement with my audience, fostering loyalty and steady growth among my talent pipeline along with creating a platform for unforeseen opportunities as the community matured.
My entrepreneurial journey has been about solving a specific problem—one that I had faced myself. My journey highlights that entrepreneurship can stem from practical considerations applied to opportunities to leverage one’s skills where they are needed most.
Have you struggled with self-doubt as an entrepreneur? How do you navigate this?
My journey as an entrepreneur has been filled with tests of my resilience and confidence. After the initial success of my first job placement, the ensuing slow season brought significant self-doubt. But even as I struggled through that very anxious phase, I knew that I could not afford to languish in negative thinking. To navigate these feelings, I've found a few strategies particularly effective.
I connected with a network of fellow female founders who have been invaluable in sharing their own experiences and insights. This has not only helped in feeling less isolated, but it’s also provided practical advice and emotional support during challenging times.
Taking time to celebrate each success, no matter how small, has been crucial. This includes even the small acts like hanging the first invoice on my whiteboard as a reminder of what I’ve achieved. These celebrations, whether small moments of positive reflection or popping a mini bottle of champagne, help maintain a positive outlook and motivate me to keep pushing forward.
Shifting my focus away from the cliched and impractical milestone of building a billion-dollar business and toward making a positive impact on a smaller scale has also alleviated undue pressure. By aiming to improve the lives of a few individuals in meaningful ways, I've been able to see more immediate and tangible results of my efforts, which reinforces the value of my work.
Regular reflection on progress made, not just in terms of financial success but also in terms of personal growth and the development of the business, helps put temporary setbacks into perspective.
What’s next for you and Ask a Chief of Staff?
We're excited to continue growing our membership in the community, connecting more aspiring and current Chiefs of Staff to share their working knowledge and diverse personal experiences that inform their roles. So far, we’ve built out interest groups by industry and geography and for Chiefs of Staff who are parents, women, non-binary, and LGBTQ+ leaders. We’re also introducing new content such as small group executive coaching and more career support so members can feel even more successful in their roles.
On a personal note, I remain committed to my own leadership journey, making sure I actively learn from peers and other entrepreneurs so I can provide the best experience to our community. This commitment is why communities like Dreamers & Doers are so valuable from my perspective. At Ask a Chief of Staff, we aspire to find places of belonging and learning through others. Dreamers & Doers has been such an inspiration for what we’re already implementing at AaCoS, and I look forward to reinvesting more of the knowledge that I gain from the Dreamers & Doers collective!
