Start-up businesses (Part 1) — How to use a chief of staff as an entrepreneur

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.

Ready to learn more about how to use a chief of staff as an entrepreneur? Head on over to vChief to read the complete article.

Madeleine Niebauer is the Founder & CEO of vChief Virtual Chief of Staff service, which offers part-time and interim chief of staff support to start-ups, nonprofit organizations, and businesses of all sizes.