Putting People First: Q&A with Group Leader Cristina Wheless

Cristina Wheless isn’t afraid to take a good opportunity when she sees it. After 13 years spent running her own software consulting firm in California, Wheless took the bold step of joining Volaris-owned AssetWorks in 2017, and she brought all her employees with her.

At the time she joined AssetWorks, her company’s customer base included several Tier 1 universities in North America, many of whom were running AssetWorks software. Her consulting firm, CKIS, had been certified by AssetWorks in 2009 as the only non-AssetWorks entity that could implement on their behalf. The CKIS team provided implementation, customization, integration, and business consultancy services. Her business was successful, growing steadily, and she’d trained people in her organization to be the best in the industry.

Shuttering the doors on her successful consulting business wasn’t even on her radar when AssetWorks CEO Tony DeSilvester approached her, asking her if she would be interested in bringing her team to his company.

“I would not have considered closing my business to work with anyone but Tony and his team,” Wheless says. “My move to AssetWorks was about the people, and specifically the discipline, the integrity, and the work ethic. I came over for the opportunity to work with individuals who are likeminded and who have shared values and ideas of what is supposed to happen in business.”

Wheless first joined AssetWorks as Chief Services Officer. From there, she was given the opportunity to advance quickly through the organization, taking on progressively more responsibility over the span of five roles. Now a Group Leader with more exposure to M&A, Wheless oversees multiple businesses and conducts deals in myriad transactions daily.

Acquired Knowledge sat down with Wheless to get insight into her life as a leader, and to understand how she puts people at the center of everything she does.

What was it like to transition from having your own business to being a leader in a larger company?

There was an adjustment period. When you’re a business owner, you’re not accustomed to anyone questioning you. You own your whole reality. But right from the beginning, at AssetWorks I was encouraged to examine the organization I’d inherited and figure out what I needed to do to improve it. So I still had a feeling of ownership over the business.

The biggest difference moving from business owner to Volaris leader was having support, best practices, and the best people around me. Yes, there’s someone who’s going to call me out if I’ve had a bad quarter, but it just made me work harder.

Volaris has taught me a new way of thinking. I often look back and say, 'Wow, what kind of business owner would I have been 18 years ago if I’d had the resources and support available to me now available to me then?'

How has your career developed at Volaris since 2017?

It has developed very quickly, but for me, appropriately fast. I went from Chief Services Officer at AssetWorks to taking on the customer development side of the house, to moving to Chief Operating Officer, then Chief Executive Officer, and then to Group Leader, all in the span of five years.

When I look at the trajectory, it was fast. I would take on a new area, do everything I could to optimize it, make it more profitable and more efficient, and then I would move onto the next one. I was used to owning a business, so it was what I expected and needed it to be. Had I moved any slower, I would have been frustrated and potentially bored.

When you’re in business for yourself, it’s hard to look outside and figure out what you need to do. Coming into this environment, I was able to work closely with a mature sales organization to structure, frame, and execute the best deals possible. Interacting with other leaders within Volaris this way, along with the support I received, helped accelerate my career and my business acumen.

Do you think your career has developed more quickly at Volaris than it would have if you’d stayed in business for yourself?

Absolutely. When you’re in business for yourself, it’s hard to look outside and figure out what you need to do. Coming into this environment, I was able to work closely with a mature sales organization to structure, frame, and execute the best deals possible. Interacting with other leaders within Volaris this way, along with the support I received, helped accelerate my career and my business acumen.

Pretty much everything in the Volaris playbook, I have leaned on. I went to best practices summits, organic growth summits, and participated in almost every competitive learning exercise available.

Volaris has taught me a new way of thinking. I often look back and say, “Wow, what kind of business owner would I have been 18 years ago if I’d had the resources and support available to me now available to me then?” These are the same kind of conversations I have with M&A prospects: “These are the resources available to you with Volaris. Take them and see how fast you grow.”

What do you see as the biggest advantage you bring to your role as Group Leader?

I have context for a deep understanding and empathy for small business owners and the challenges software companies face. These are people that have built companies from the ground up – many of them bootstrapped without outside funding. They’ve invited employees into their world, taught them what they need to know, and their employees add value. At the end of the day, being a small business owner is a huge responsibility and the vast majority of small business owners take it very seriously.

As I’m talking to prospects who are looking to either exit or grow their businesses, I can articulate why Volaris is a good home for their business and for their employees. Because everything they did in their environment, we’re going to do. We’re just going to do it bigger, and with more support and with more focus than they have in a more myopic environment.

What makes Volaris a good home for these businesses in your mind?

The Volaris model compels everyone to focus on what really matters, which is people. We are an operating group that acquires vertical market businesses. But we don’t just acquire the businesses, we acquire great employees, and we help them achieve their potential so we all can prosper. It’s a way to conduct business with honor.

And I say to companies that are considering joining Volaris, our interest is not in flipping their business in five years for a profit. The fact that we buy and hold forever gives us a unique opportunity to find talent in these organizations and to preserve the business’s legacy and its culture. It’s our goal to find those people in your company and build them up.

You recently oversaw a business split at AssetWorks. Tell us how you approached that process.

I’m a self-described business split enthusiast. When a business grows to the point where your customers have different priorities, or they’re in different industries, or you’re attacking different geographies or market segments, it’s time to look at options for regaining focus. When you get to the point where there are more priorities than there are people, your business starts to feel like a jack-of-all-trades, which means you’re the master of none.

The AssetWorks split was finalized in January 2022, which gave FacilityForce the opportunity to set business priorities that were distinct from AssetWorks. It wasn’t easy, but it’s given us the opportunity to strengthen our bench, and better service our customers. We can now develop more leaders in AssetWorks and FacilityForce, and bring focus to the customers and geographies, and verticals we are pursuing. Ultimately, this has allowed both companies to grow in a way they need to, and in a way that they couldn’t have done together.

A business split means growth for everybody. A split is a way of allowing the best people in your organization to double down, focus, service their customers and grow. And as a result, we have two companies growing faster than one company could have grown.

How do you see yourself as a leader?

I spend more than half my time coaching, mentoring, working on leadership development, and building succession plans. What matters most is our people. Without a strong bench of leaders and succession plans, there’s no way we’re going to grow.

As a leader within the company, people may see you as a role model. What does that mean to you?

I would tell anyone who’s looking at me as a potential role model, it’s a ton of work. You can have it all. You can have and build and grow a career and a company, and at the same time you can have successful relationships and be a parent. If you’re willing to put the time in, you can have your cake and eat it too.

I’m very happy and content with the way my adult life has unfolded so far. And to the extent that anyone considers me a role model, I’m happy to share my experiences as a businessperson, how I’ve positioned myself, and why I made the choices I made. I’m happy to have those conversations all day long to help anyone looking for their own path to find it.

What advice would you offer people looking to start a career at Volaris?

Do it, for one. Don’t shy away and don’t be intimidated. Imagine yourself as a sponge. There’s so much out there for you to learn, just soak it all in.

This is an environment where, as your career progresses, you can be shaped into the best possible leader. If you keep an open mind and you’re willing to work, this is the best environment, without exception.