Start-up businesses (Part 3): Lessons Learned at vChief

I thought a good way to wrap up our startup series would be to share some of my own lessons learned as the startup founder of vChief. I started vChief as a side hustle, working as a chief of staff myself. I found the role exhilarating because it was a great mix of strategic planning, ​​day-to-day execution and implementation of projects, and uplifting a leader to be her best. I also quickly realized the benefits a chief of staff could provide to startup leaders.


I began to envision the chief of staff role differently from the traditional model. Why couldn’t the levels of support be molded to fit the needs of a leader? I was passionate about providing this level of service to clients, but I also was learning my own lessons about being a startup founder as I went along.


I’m going to cover the same key points our client partners covered in parts one and two, adding my own experiences as a founder of what began as a very lean startup and has grown into something much bigger than I could have imagined six years ago.


Using your chief of staff as an entrepreneur in your business

Let me admit something right off the bat: I held off a long time in hiring my own chief of staff. Even though I fully believe in the benefits of having a chief of staff–clearly, it’s my business model!--I felt like I didn’t need one right away, because I am a chief of staff! It wasn’t until the volume got high enough that I realized I couldn’t actually manage it all myself.


Having spent many years as a chief of staff, I thrive in that do-it-all role with my pulse on every aspect of the business. I completely understand wanting to keep all the plates spinning on your own terms. Your startup is your “child” in a way. It’s something you created, and likely envisioned well ahead of the actual existence of the company. No one would argue the point that a founder is the most attached to their business.


While that passion, dedication and drive are unmatched, causing wonderful things to happen in your business, they can also lead to overwhelm, stagnation, and shutting down progress without you even realizing it.


This is why it is essential, if you want to move the needle forward, to bring in a trusted thought partner who gets the business from your angle, yet can take their own unique perspective and experience and offer some new and innovative ways of doing things, organizing systems, and running operations. These are the chief of staff’s responsibilities.


But I humbly admit that I spent the first four years in business trying to do it all. About six months into our current growth spurt, I knew I needed support, because I was working way more than I wanted to. As soon as I let go and utilized the incredible power of my own chief of staff, my business grew even more rapidly, and our ability to serve clients expanded. I hired my chief of staff at the start of 2021. We grew 300% that year. We could not have done that without my chief of staff and the other central team members we hired.


Here are a few ways I have used my chief of staff as an entrepreneur at vChief:

  • Strategic planning. As vChief charts our path forward in 2022 and beyond, my chief of staff has led the charge to identify our priorities, goals, and metrics, and review our progress on a regular basis.

  • Setting strategic priorities for me as a leader. My role has shifted fairly drastically from 2020 to now. I set priorities and metrics for myself as a leader, in the same way we do for our company, and my chief of staff facilitates that process, and holds me accountable to spending my time in ways that are aligned with those priorities.

  • Planning our team retreat. I said “I want to host a team retreat in February in Puerto Rico.” Then I promptly forgot about it and let her run the entire thing from planning to execution. She drafted the slides, prepped my talking points, and ensured I was ready to lead without doing all of the pre-work required to get there. She and my executive assistant planned all of the logistics, meals, activities, and sessions, so I didn’t have to.

  • Enrolling in benefits. When we brought on employees to our central team for the first time in 2021 (we had used contractors exclusively to that point), we needed to figure out benefits for them. She researched and got us enrolled in 401K, health, vision and dental benefits.

  • Managing my executive assistant. I was so excited to add an EA to our team this year. She’s stellar but also new to the EA role, and it is wonderful to have a chief of staff who can guide her professional development

  • Meeting planning. My chief of staff leads the planning for all of our team meetings, leadership team meetings, and professional development sessions for our chiefs of staff.

  • Miscellaneous fire-fighting. As we all know, there are urgent situations that arise as we lead our work day to day. It is amazing to be able to have someone who you can just assign the one-off things that need to be dealt with but that are distracting from the work that has the most impact.

Adding a chief of staff to your roster adds enormous impact, leveling up how you function as a leader and founder, and how your business functions and provides service to its customers.


Building a team when the time is right

I think adding a chief of staff as one of your first employees is a great way to add leverage, especially if you are a sole business owner (or even functioning as a partnership). Among other things, your chief of staff will help you organize your systems and evaluate where you are lean.


Once you have a sense for where you have some gaps you need to fill, take time to be thoughtful about what those roles will look like within your organization and what type of people you want in those positions. Let your chief of staff help guide the hiring process. This may even be the ideal time to strategize the next step on the career path for your chief of staff.


I worked for a long time as a sole founder, with only a handful of independent contractors who I outsourced work to because I either didn’t have the time or interest in doing it. Now that vChief has grown as much as it has, I need people working on dedicated operations in a more long-term, full-time capacity.


Some areas where I quickly filled the gaps by building a team:

  • Accounting

  • Establishing a digital presence

  • Communications and content development

  • Business development

As vChief grew, one of the first areas I had to intentionally pull myself back from was getting involved in every client interaction. It’s one thing to lean in when you have 20 clients, but once we reached 75 clients–with the potential for exponential growth beyond that–I quickly realized I can’t be the one who solves every issue. It was necessary to start asking strategic questions:

  • How do we manage consultant placement, and how can we systematize it so the knowledge doesn’t just rest with one person (as it did with me for a long time?

  • Do we fold customer relations into our business development roles or create a client success role or team?

  • What is the best way to manage our finance function with in-house and external support?

  • What technology systems can we build that integrate the many aspects of our work and can make our team operate more efficiently?

What are some areas in your own business where you can let go, and bring in someone more specialized?


Building an org chart

In part two, which focused on building an org chart as a small business, our client partners shared some tips that were unified across businesses:

  • Focus on your personal strengths and maintain those within your business; delegate and hire within the other areas needed in order to accelerate growth

  • Be proactive in aligning your team’s strengths with the growing needs of your business

  • Have a leader on the team who can focus on the long term vision while also staying attuned to the present and how to get from here to there

  • Define your long-term goals


We’re getting to the stage of organization with vChief where other people need to be making decisions and I can’t be involved in every decision, so I’m figuring out how to pull myself up and out and empower other people to drive those decisions. This is where building an org chart comes in handy, and can help you decide:

  • who owns the decision

  • who is consulting

  • who has veto power

Personally, designing an org chart has been helpful for me to envision the ways in which I can move forward in my business. It’s not that I want to take a step back, but I want to grow the internal team so that I can play a new role again. We’re in a transition phase where other people are starting to own things like the finances and client relations, freeing up my time for high level management and brand building.


Once you have a vision for where you can go and you determine your unique value add as a leader to get to where you want to go, you realize you don’t have to do all of the things to make your business run. You are specifically gifted at doing some things that will get you to that vision point, but what can you give away to other people? This is the beginning framework of your org chart.


Remember, you started this venture because you had a vision of how you can solve a problem or make something better. Don’t lose sight of that as your business grows. Rather, embrace that vision even tighter and communicate it loud and clear to others as you bring them on for support and encouragement towards that vision. Figure out how to delegate, automate, and push through growth in a positive manner, continuing to provide exactly the type of service that each client needs while staying true to your high level goals.