vChief's 5 Year Anniversary: Part 1 - A Jump into Entrepreneurship



It’s hard to believe I wrote my first blog post five years ago, introducing

my new venture and enlightening business leaders on what is possible with a chief of staff supporting you virtually. As we celebrate our fifth anniversary, it seemed fitting to reflect on ho w far we’ve come since those early days when I first took the leap into entrepreneurship. I’ll be posting a five-part series on lessons learned, opportunities for growth, successes we’ve celebrated and everything in between.


Celebrating Success

As I look back on the successes we’ve had in vChief over the years, what I’m most proud of is

the fact that we intentionally built a company that is very representative of the future of work, both for employers (our clients) and for our team members. Simply put, we were virtual first, and we’ve never been anything other than virtual. Although that might not be a perfect solution for everyone and every situation, I do think more people are clamoring for that because of the flexibility it allows in their lives.


We’ve also found that our method of working with our clients, by bringing in talent in a way that is flexible and can adapt with a client’s needs as they grow or as they lead different initiatives, has really resonated. Not every client needs a 40 hour-per-week solution to their talent, and we adapt to that in ways that support their business at every stage of growth.


On the consultant side, there are so many people who want work options that are flexible, part-time and remote, we’ve never had any trouble finding talent. Our talent is the main thing that differentiates us from the competition--they’re a cross-section of MBAs, JDs, certified project managers, former executive directors, and more. We always receive positive feedback about our talent: 98% of clients surveyed would recommend vChief to a friend. That’s really validating for me as an entrepreneur, coupled with the fact that we’re creating really flexible opportunities for people that enables the work-life balance our team members crave.


I’m a prime example of being able to take work-life balance and build the life that you want. I took the first steps to start this company while working remotely from Costa Rica. The fact that I’ve been able to travel with my family for over eighteen months out of the five years we’ve been running this is a testament to what you can do when you have that kind of flexibility. We also have team members who have worked from the Dominican Republic, Columbia and Myanmar! We have team members who are founding their own ed tech companies while working for vChief. And we have dozens of working parents who use vChief to give them the flexibility they want to have quality time with their kids and truly meaningful work experiences at once.


Leaning in to Failure

Maybe this doesn’t quite fit in the “failure” category, but something we’ve been thinking about a lot lately is our strategic growth plan. If I could do it all over again, I would have thought earlier about our strategic growth, and crafted a plan around how I wanted that to look. We spent our first four years growing organically, which was great because we were so lucky to have a strong pipeline of referrals. It took me a while, however, to really consider how to grow strategically and what that meant in terms of how we grew our team and also how we changed our systems.


Right now, we are going through an incredible growth spurt, which is exciting. We have proven our model, and there is strong demand for our services. But we’re also feeling the bottlenecks and the inefficiencies of our systems. In hindsight, it would have been nice to fix some of those inefficiencies as well as be able to anticipate what we needed on the staffing side to really approach the growth we’re having now in a way that feels more sustainable.


Leveraging Lessons for Business

Reviewing our wins and areas for opportunities allows us to leverage them in growing our business. Regarding the future of work, our flexibility and remote work stance are values we live by. Our team members live by it and many of our clients aspire to it. We love that we can help leaders find more flexibility in their own days by providing them chief of staff support. Hopefully that will enable them to delegate things and find more flexibility for themselves. I still stand by what I said in my first post: “I have seen how invaluable [the chief of staff role] has become to the leaders I support. I see it when we are finally able to squeeze in an hour of ‘thinking time’ or extra family time each day, amidst all of the meetings and travel on their calendar.”


We often work with clients who are in the same state of affairs that we’re in now, experiencing significant growth and feeling the pain points and lack of time to get everything done. That’s when they decide to bring in a chief of staff to help solve those issues.


It would be great if we can get to clients before they get to that point, to help them plan ahead for big growth spurts, in ways we wish we had done ourselves. We’re still figuring out where those types of clients are and how to find them, and then convince them they need this before they’re to the point of feeling overwhelmed in their roles. I know that’s something we can continue to think about and work on as we reach out to new organizations.


Next up, I’ll be talking about the most valuable lesson I’ve learned as an entrepreneur.