8 Years of Trajectify: Every Solution Creates a New Challenge

About three years ago, I was out to dinner with several Trajectify coaches. We were celebrating the end of the year, Trajectify’s fifth year in business, and they asked me a question that I struggled to answer. 

They wanted to know whether Trajectify was ‘Mike’ or whether Trajectify was something bigger. 

Was I building Trajectify to be a lifestyle business or something more? 

Up to that point, I supposed I had been building a lifestyle business. As I pondered their question, I knew my answer — I wanted it to be something bigger. 

If Trajectify was going to scale, I had to be more strategic about it. 

On the one hand, I could say that I’ve been successful. In 2020, we were number 23 on Philadelphia100’s list of the 100 fastest growing businesses in the Philadelphia region. The recognition was appreciated and a clear external indication that we are a scaling company, not just a guy doing some coaching.

On the other hand, when you’re small, it’s easy to grow rapidly. Does that recognition really mean we’re scaling the way I’d like to? Three years ago, we decided to increase our investments in content, and when I look at Trajectify’s website, our articles, our email newsletter — there’s still a lot of Mike. 

So how am I really doing on that goal to turn Trajectify into something bigger?

I’m going to share some of the ways we’ve grown in the last three years. I’ll also pull back the curtain a bit and share one of the main places I’m struggling. And there will always be struggles because every solution creates a new set of challenges. 

Growing the business 

In the last three years, I’ve made a number of investments to increase both the depth and breadth of Trajectify’s offerings to clients. 

We added organizational assessments to our roster of services. We were then able to help organizations more systematically — starting in the midst of the organization and moving out, up, and down. It’s a powerful way for an organization and its leadership to understand what’s happening inside and use that to make a growth and change management plan. 

Near the end of 2018, I got certified with The Alternative Board to run peer advisory groups. I had always tried to organically build these boards, and using their structured and proven methodology delivered even more than I’d anticipated. 

We grew an advisory board that is effective for both the members and us. The participating CEOs have received significant insight and support from each other. Plus, it’s became a lower investment opportunity to begin working with us. We’ve turned many of those members into successful Trajectify engagements. 

Recognizing that many of our clients needed services we weren’t yet offering, we expanded our team to bring on Jim McMonagle to offer CFO services and Lisa Peskin to offer sales coaching. 

As a result of all these investments, we’ve grown the average size of our engagements. We continue to help clients not only scale their organizations and grow their leadership, but we’re also helping them through capital and other major transactions. We’re getting into the trenches more as part-time interim executives, working in the trenches with clients side by side. 

Growing through the pandemic

And of course, we weathered a pandemic and its ensuing unpredictability (and continue to do so). 

While we’d previously done some work remotely, the intimacy of coaching benefited from in-person interactions — or so we thought. The pandemic taught us how to get that same intimacy remotely. We also helped organizations make the remote work shift themselves. 

As was the case with many businesses, the pandemic created an opportunity we weren’t expecting. We had an “aha” moment: if everyone is operating virtually, then a leadership coach or a growth strategist in Philadelphia is no different than one in Boston. 

We could now compete without geographic boundaries because we weren’t at a geographic disadvantage in comparison to local coaches in other places. We began to spend more resources looking beyond Philadelphia to do business development. Business development without boundaries is still a work in progress for us and we haven’t landed too many clients from this prospecting.

Still, it’s an opportunity we’re carrying forward. 

Challenges to growth 

At that celebration dinner three years ago, I named the desire to create something bigger with Trajectify. In several ways, I’ve delivered on that plan. 

At the same time, there’s a key area that continues to be a sticking point for me and for Trajectify’s growth: scaling beyond myself. 

In the early stages of a services business, the person who founded the company is the person who’s out there selling. Ultimately, there comes a point when you either need to scale because you can’t sell anymore of yourself or you need to put a cap on your services. 

It’s a conundrum because there’s a lot of evidence out there (and everyone who’s built a service business agrees) that for the first few million in revenue and couple dozen employees, people want to buy from the CEO. You’re too small to have an effective salesforce. 

The best plan is still for the CEO, the founder, to be out there selling. Of course that means their time delivering services is limited. 

It’s an easy place to get stuck. When the founder is out there selling, people are so interested in them that they don’t want to buy other resources — or from a sales manager. If the founder doesn’t find a way to productize their services, it is difficult to scale. 

To be totally candid, it’s a place where I still get a little bit stuck. I love to schmooze and tell stories. I love to build relationships. It’s how I’ve bootstrapped a business. 

I’m great at selling relationships. What I’m less good at: selling products. 

So, how do I get unstuck?

New solutions and new challenges

I’ve considered something I’ve coached many clients through: bringing partners into the business. 

Right now, I’m the only one with skin in the game. Yes, I have fantastic coaches — who aren’t partners in the business. 

Creating skin in the game for someone else is one of the most important components you can do to move from a founder-led services business to a scalable services business. 

So, looking to the future, I’m considering the same things I coach my clients to think about in choosing a partner. The two that are most relevant to me right now are:

• Complementary skill sets and diverse thinking. You know the saying — if there are 10 people in the room, and they all agree, then nine of them are unnecessary. I look for those that bring skills and thoughts to the table that we don’t already have. 

• Network. I’m working with a client who’s looking for a business partner in another region because he has a lot of business opportunities there but isn’t part of the local community. I could seek a partner in a different location and further our geographic expansion. 

I’m also going to have to get some psychological work done on myself. When Trajectify scales and I bring in partners, the business won’t be all about me anymore. I started a business to be in control. We know that many entrepreneurs are control freaks. Now I’ve built to a point where I need to let go of some of the control. And again I think that every solution creates a new challenge.

I’ve been working with a client who followed such a trajectory. He ran a professional services firm and was struggling to scale. He decided to sell his company and become part of something bigger. Without taking money off the table, he rolled it over to own a piece of the bigger company and became a member of the management committee. He traded control for the opportunity to be part of something bigger. 

And that solution presented new challenges. He’s continuing to learn how to participate in decision making in a whole new way.

Final thoughts

One of my lessons over the past three years has been that every solution creates new challenges.

I spent the first five years building Trajectify into a stable lifestyle business. During that time, I surprised myself by deciding to also join another startup. I shared Trajectify’s service delivery with two other coaches to free up some of my bandwidth. Perhaps I’d laid the early groundwork for a business that was bigger than myself. When I came back, they stayed, I focused on biz dev, and we restarted our growth. 

We’ve accomplished big things and helped our clients accomplish even bigger things. Every step along the way has solved one problem and created new challenges for me to navigate. 

Thank goodness they do. I thrive on persistent learning and growing alongside my clients.

Here’s some of what we’ve been up to the last eight years:

In 2014, 75% of our clients more than doubled their revenues for the calendar year. I was named A Most Admired CEO for my work at Trajectify by the Philadelphia Business Journal.

In 2015, two clients received acquisition offers. One sold for 25x revenue, too rich to turn down, and we coached them through the process. The other had so much confidence in their growth and future opportunity, they didn't accept the offer and continued to double revenues each year. Trajectify’s talent expanded to include its first two coaching partners, Chuck Hall and Joe Spinelli.

In 2016, 5 of the top 25 companies ranked in the Philadelphia 100 worked with Trajectify. The program identifies and honors the 100 fastest growing, privately held entrepreneurial companies in the Greater Philadelphia Region.

In 2017, 5 Trajectify clients were on the Inc. 5000 list of fastest-growing private companies in America. One of our clients exited for 5x revenue. Joe Cotellese joined us as Product Management coach.

In 2018, Trajectify client My Independence at Home was named SBA Minority-owned business of the year. We increased programming in NYC, including Bootstrappers Breakfasts. We launched The Alternative Board (TAB) peer advisory boards. We held the first Trajectify Live Business Growth Conference and Leadership Retreat. We added clients on the West Coast.

In 2019, Trajectify experienced its greatest growth ever, more than doubling revenues. We moved our offices into Offsite at Fitler Club. We introduced new products like the Organizational Assessment and increased focus on interim CXO assignments, getting in the trenches working side-by-side with more clients. We hired our first full-time Business Coordinator. We expanded to add clients in NYC, Baltimore, and Boston.

In 2020, Trajectify won the Philadelphia 100 award for being one of the fastest growing private companies in the region. Coaches Henna Pryor, Russ Cherry and Lisa Peskin joined our team, as did Business Coordinator, Ralph Thorn. In light of the COVID-19 crisis and resulting business and economic environment, Trajectify launched new workshops and content to engage more leaders as they faced great uncertainty. Two Trajectify clients were acquired in life-changing events for those business owners. Our growing list of clients also continued to increase its presence on the annual Inc. 5000 list.

I can’t wait to share what we’ve done in 2021. We’re staying strong to help keep you strong, overcoming each new challenge that every solution might bring. It’s growth.