What exactly is a Chief of Staff?

Having experienced the value of the CoS/founder partnership, I’m a huge advocate for both founders and the generalist-CoS-types who can find great success and fulfillment through it. Here, I’ll share a little of my personal experience. Eventually, I may build out more comprehensive resources.

If there’s one theme you’ll see repeated again and again when people talk about this role, it’s how versatile it is. The actual shape of the role depends on what the Chief of Staff brings to the table, what kind of work the organization is doing, and where the principal most needs support.

I’ve known CoS leaders who came from all kinds of backgrounds, ranging from marketing, education, consulting, product, engineering, government, and others. Naturally, each brings a different lens and set of strengths.

My own background has been rooted in startup operations, people/HR, and online community building. So the things I’m drawn to tend to fall into those categories. That said, a CoS can typically cover some version of the following:

  • Focus and prioritization

  • Support through moments of scale, transition, or uncertainty

  • Strategic planning

  • Translating vision into clear execution plans

  • Building internal operations functions (People, Admin, BizOps)

  • Managing executive-level communications and information flow

  • Designing and facilitating meetings

  • Organizational design, role clarity, and team structure

  • Developing leadership teams

  • Structuring and managing complex projects

  • Creating values-aligned policies and SOPs

  • Shaping culture

  • Supporting team and community engagement

Why I love the Chief of Staff role (and why you might too!)…

I frequently get asked why I am drawn to startups and why I choose to specifically work in this role. Like most CoS I know, I didn’t intentionally choose this role or path; it was a result of integrating things into my life that felt natural and allowed me to step into work that energizes me.

This is the first role that I’ve ever been in that has put me into a near constant flow state. I credit this to the adaptive nature of the role and the wide variety of tasks that keep me just at the edge of my capabilities.

One of the things I appreciate most is that there is a good balance of strategy, implementation, and relationship building. As it turns out, this is a valuable and complementary asset for founder-like people who produce a lot of unstructured ideas and relationships, without the time or discipline to manage everything downstream of that.

For better or worse, I am a generalist and enjoy having a lot of breadth to my role. To some extent, this may be a byproduct of having been in the startup world for so long, but I think that the startup environment gave me a place to find the intellectual stimulation I naturally craved.

I’m always searching for the place where I can be upstream of as many issues and opportunities as possible. I also work best in long-term, partnership type of roles, where I can really get to know the people I’m working closest to and leverage my operational strengths to support their effectiveness. This role checks those big boxes, along with many others.

Finding the Right Principal–CoS Partnership

When people reach out to me asking how to become a Chief of Staff or hire one, I always say that one of the most beautiful things about the role is that it never looks the same. It is a highly adaptive role shaped around the needs of the person or people it supports.

This is why it’s notoriously difficult to find a good match. These roles and the people who fill them tend to be shaped in very unique ways. This is true of all people, but it’s more pronounced in these support-oriented roles where you need to be on the same wavelength.

Whether you’re seeking a role as a CoS or you are a founder who is looking for a great person to support you, the most important thing you can do is take the time to really understand the alignment and nuances in values, skillset, needs, and personality. Assuming skills and values alignment, also ask yourself:

  • Would I want to be around this person? Every day?

  • Does this person seem like the kind of person I can respect and trust?

  • Do we communicate in a natural, unforced way? Does our energy flow easily?

  • Do they inspire me? Do I think I can learn from them?

In my own career, as well as when hiring others, my mantra is: if it’s not a clear “hell yes!” (on both sides) then it’s a NO.

If there are hesitations, don’t underestimate them. Every human has idiosyncrasies and areas to work on. You’re not looking for perfection. But you should feel a strong yes in your gut.

Hard skills are important but so is your gut feeling. On paper, someone might be great but you just don’t “vibe”. Listen to that. Your body can tell you things that your brain cannot make sense of. Every single time I’ve overridden my intuition, I’ve regretted it. And, conversely, when I’ve listened to my gut, I generally do not regret it. Also, keep in mind that you can train most skills, but you cannot train on values alignment and being a good match on the other dimensions.

Personality Profile

I’ve taken several personality and working style assessments over the years. While I’m aware of their limitations, they’ve helped me put language to how I tend to show up at work, both in my natural strengths and in the areas I need to stay mindful of.

I’m sharing a few of my results here because they might help you identify some of the traits that often show up in strong Chiefs of Staff or generalist operator types. Every CoS looks different, but there are some common threads.

DISC (Mediator)

  • Sensitive, loyal, and emotionally intuitive

  • Values accuracy, quality, and systematic thinking

  • Prefers stability, but enjoy new people and stimulating projects

  • Takes calculated risks and favor deliberate, meaningful change

  • Outgoing, enthusiastic, and persuasive with both logic and emotion

  • Diplomatic; seeks win-win outcomes in conflict

  • Makes thoughtful, people-aware decisions based on research and high standards

  • Skilled at connecting ideas, people, and concepts

Myers-Briggs (INFJ)

  • Complex, multi-talented

  • Humanitarian and idealistic

  • Blends vision and practicality

  • Cares deeply about people and society

  • Sometimes mistaken for extroverts

  • Thrives on deep, long-term relationships

  • Strong insight into others’ motivations

  • Empathic and emotionally attuned

  • Expresses themselves best in writing

  • Systems builders grounded in people and values

  • Quietly impactful; contributions often hard to quantify

WorkingGenius (Discernment + Enablement)

  • Intuitive, human-centered judgment

  • Quickly spots strong ideas and improvements

  • Rooted in pattern recognition, not guesses

  • Balances practicality, common sense, and emotional intelligence

  • Trusts gut—often right, even without data

  • Helps others move ideas forward

  • Flexible; doesn't need control

  • Encouraging, responsive, and dependable

Kind Words from Others

  • Brandi is a leader that inspires me a great deal. Her work ethic is beyond impressive, this is a woman who will not quit until the job is done. Brandi’s firsthand knowledge of creating and fostering online communities and her experience is hard to match. She’s able to keep her eye on a dizzying amount of moving pieces, while nurturing the employees she manages, building and sustaining excellent relationships with clients and business partners, and making time for her own personal development, always learning more. A true expert in new media, project management, client services, meeting the needs of the world’s biggest brands, and developing personnel to be their best – she’s an epic asset to any team.

    Rose

  • Brandi. Brilliant. Reliable. Awesome. Natural. Dynamic. Inspiring. These are some attributes off the top of my head when Brandi comes to mind. Our paths crossed many times, and I was always impressed just how much she was loved by her team. Brandi has this innate ability to meet challenging projects and demanding clients with natural enthusiasm and the utmost commitment. Simultaneously she gave her team guidance, confidence, concise instructions to be able to achieve the maximum productivity to get the job done. I recommend Brandi wholeheartedly without the slightest hesitation.

    Roland

  • Brandi is one of those people that everyone wishes they could have on their team. Insightful, articulate, ethical, personable & client-focused are just a few words that come to mind. She is a well-rounded professional leader that gives everything she touches her all.

    Lindsay

  • Brandi is a truly inspiring leader. She has been instrumental in giving me a chance to prove myself; providing guidance, encouragement, and very precious advice. This has helped me advance my career, develop my skills when it comes to social media/online content management, and transition to a full-time dedicated employee. I highly recommend her as she would be a great addition to any team and a valuable asset.

    Jad

  • An excellent manager, she is always positive, constructive, and solution-oriented. She is hard-working, loyal, and relentless. Her attitude is infectious, making everyone around her better. Brandi treats adversity as an opportunity to learn something new. She embraces organizational change, is industrious, and is constantly in the process of reinventing herself. She devotes a considerable amount of her personal time to learning –something which she does for the benefit of her employer and her clients. Brandi’s biggest talent is her people skills. Her clients and coworkers love her, and she has also groomed some of our finest managers and moderators. Any organization would be lucky to have her, and I recommend her without hesitation.

    Bryan

  • Working with Brandi was one of the highlights of the job! She is very good at what she does; she is a good communicator, positive, affirming and full of ideas!

    Beth

  • I’ve never met anyone who cares about people as much as Brandi does. She is constantly striving to ensure the best possible experience for her clients and team members. Brandi has great attention to detail and an incredible work ethic. It is my pleasure to recommend Brandi as a confident, capable team leader and colleague.

    Jan

  • Her positive attitude is infectious, and she brings joy to her entire team. She is reliable, confident, organized, efficient, competent, productive, and one of the best relationship builders I have ever met.

    Craig

  • Brandi has a true love for her work. Whether it is her co-workers or clients she will do what she can to deliver the best possible results and to make sure everyone is taken care of. She is great at encouraging those around her to deliver work to their own best abilities as well.

    Kris

Brands I’ve Worked With