Start-up Businesses (Part 1): How to Use a Chief of Staff as an Entrepreneur

Written by vChief

December 23, 2021

I’ve talked time and again about the benefits of enlisting support from a chief of staff when you are in the grind of developing your startup. Living the life of a startup founder can be incredibly rewarding, but also very lonely and overwhelming. Having a trusted partner who can help you plan and develop your business is key.

This time around, I thought I’d share some words of wisdom from our vChief clients and their experiences in utilizing a chief of staff within their organization as they figured out how they wanted their company to grow.

Feedback was shared by:

  • Kishan Madamala of Maxton & Company, eCommerce business which sells niche office supplies and accessories
  • Nicole Jarbo of Goodbets, a boutique fundraising firm
  • Joanne Hill-Powell of LiftEd, education technology company serving special education programs by providing data to help advance learning capabilities

Settle in and learn what these three clients discovered as they vetted a chief of staff to guide them in their startup journey.

How does your chief of staff function like an entrepreneur?

KM: We’re a small company. If you’re going to have day to day work, you probably have a regular team of employees and contractors taking care of those responsibilities. But we’ve grown substantially over the past ten years. We have more corporate work and work done outside of the day-to-day.

For example, moving our headquarters…[there was a lot involved in] this change: shutting down the old space, dealing with local government, changes of address with major vendors, utilities to open accounts with, taxes, local administrative fees and costs. Our chief of staff was able to handle all that for us.

NJ: A lot of the work I do is very creative, and it’s often external facing for people. Clients come to us and have a very vague idea of what they’d like to accomplish. They know they want it to be meaningful or influential in the space or achieve certain outcomes, and I help them design the most effective strategy. And we’ll support the execution if they don’t have the energy to do that.

The chief of staff I work with the most is really a thought partner to me, helping me draw out these more nuanced kinds of things we’d want to think about, like a communication strategy. [They see] things I’m going to miss, helping make sure we meet a certain level of quality that we want to put out there. [They] support me in doing a lot of the work I would be doing myself: thinking, strategizing, analyzing, envisioning, refining.

JHP: The one key piece to entrepreneurship is being able to wear several hats. Particularly at a startup level, you’re expected to perform in so many areas with or without expertise, but the great thing about our chief of staff is she works hand in hand with me as a cofounder and our CEO to operationalize our sales efforts. She had a very rich background already on processes around sales…she came in and immediately helped us to develop a new system…and then she collaborated with us about being a lot more strategic around our sales goals, our metrics, and our go-to-market strategy.

[She was] able to look at other areas of our business operationally…we know we have a platform that can help to support a problem that’s very ripe right now but at the same time our business is struggling and we need to be very intentional about every dollar. She was able to play both of those sides every single day, and think about the problems we’re facing today but the solutions that take us forward.

She [also] played a key role in communicating our updates to investors real-time. In the midst of all that, although we’re a small team, she was thinking about onboarding anyone new to the team, and maintaining the morale of the team. I absolutely feel like that defines entrepreneurship: you’re nimble, meet the needs of today, thinking about tomorrow and willing to constantly be lane-switching and hat-changing.

When did you know you needed a chief of staff?

KM: I remember when Maddy was starting the business, one of our regional friends had shared her post and I thought it was a really great idea. That was about 5 or 6 years ago and, at the time, I thought this is exactly perfect for somebody like me. I only had 4 or 5 employees and was mainly focused on operating, but what I could use some help on were other important tasks, one-off tasks that still needed to be done.

I use my chief of staff a little differently from others. I don’t have my chief of staff do any scheduling or helping to manage my time. I assign them more on special projects, one-offs that need to be done well. It’s something that would otherwise fall on me so knowing I can trust somebody else with those things is a real load off my plate.

NJ: I knew I needed some support, with the consulting [work] I had started, but I really understood I needed help when I ended up in the ER and needed emergency surgery. Clients were still emailing me and asking for things. I started this venture thinking it would give me more freedom; I realized that wasn’t necessarily true. After that, I reached out to get some more help.

JHP: We’re really fortunate to be working with vChief through some leveraged support with our lead investor, Camelback Ventures. Because of our startup needs, they helped to subsidize the cost. We knew that we had this need long before we were able to access the need and services.

What do you wish you knew then that you know now?

KM: When you bring on a chief of staff, you’ll want to get to know the person and understand where their strengths are and how that interacts with the strengths of your own team, and make sure that you’re selecting somebody with a complementary skill set. You want to have somebody you have a real rapport with.

NJ: The same thing I want to see in our clients: understanding what is the end goal. A lot of the folks we work with in the nonprofit space have ideas of doing things but often don’t have a very clear idea of what the outcome or output should be. We help them visualize that and understand how it’s going to meet these more intangible ambitious goals they have. That kind of outcome is real deep understanding and a vision for where I want to take the business and what I want to accomplish.

JHP: So much advice, but I think in the context of this conversation, it would be what a value add a chief of staff is. As a founder, you’re trying to do everything. We thought ‘we can’t hand this over to anyone’ until we figured it out. We’re still working on product market fit, we need to get that feedback and refine how we sell and go to market with our platform, but the level of support our chief of staff has provided has enabled us to really focus on the areas that truly only we can do best.

Also, to advocate for this level of support sooner, because this has been really an integral part of us being able to focus on the most impactful work as founders.

I’m grateful to these founders for sharing their perspectives, providing us a better picture of how each business uses their chief of staff for support in unique ways. While each of these entrepreneurs have their own experiences, I heard a few common threads across each of their journeys.

First, trying to “do it all” yourself is not a successful business model. All three founders admitted they needed additional support, which is a message I also spread loud and clear. Finding that trusted advisor in your chief of staff can work wonders.

When you decide a chief of staff will add value to your startup (and they will!), find someone who thinks slightly differently than you and has a skill set that complements your own. You don’t need a carbon copy of you but, rather, an individual who will bring a fresh perspective and mindset to your organization.

Finally, communication is essential, both with your chief of staff and anyone else involved in your organization. Be very clear and direct about your goals for how you want the organization to grow. And remember that a chief of staff can be utilized to help you build a communication strategy and ensure you are reaching customers, whether current or potential, in the way you want.

There is so much power and value in adding a chief of staff to your organization, and it doesn’t have to be a full-time commitment. We work with our clients to create a chief of staff package that works for your needs, because every startup is an individual entity with distinctive features.

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