As Volaris Group celebrates its 30th anniversary in 2025, we are publishing a series that looks at the people, businesses, and milestones that have helped build and grow our ecosystem of software businesses into what it is today.
When U.S.-based government services provider MAXIMUS decided to divest its asset management software divisions in 2008, it turned out to be Constellation Software’s Volaris Group that was the lucky buyer.
Richard Montoni, CEO of MAXIMUS at the time of the sale, expressed confidence in Constellation as an acquirer of the businesses, citing a “long-standing record of successful software implementations” as standing behind his belief that the buyer could capitalize on the core capabilities and opportunities of the intellectual property. It was a winning outcome for both buyer and seller: MAXIMUS could refocus on its core offerings, while Volaris set out to grow the former asset solutions division over the long term.
17 years later, the results of that deal speak for themselves. The asset solutions businesses that grew from the initial acquisition are still with Volaris Group. Rebranded and unified under the name of AssetWorks, the group has grown into several distinct verticals that operate independently and include: Fleet, Appraisal, Facilities, Higher Education, Government, and Risk Management.
Within Volaris, AssetWorks has become one of the best-known long-term successes out of the early corporate carve-out transactions completed by Volaris. The growth of AssetWorks has spread between two portfolios over those years, sharing the successes of many leaders between them.
Long-Term Growth at AssetWorks: From 2008 to 2025
While the initial success of a carve-out acquisition focuses on short-term goals, other benefits can take a longer period of time to play out. AssetWorks is an example of how the right acquirer – one that understands software and can give the acquired business the right attention and investment – can inject new life into a business where it was previously stagnating.
If AssetWorks had been sold to a private equity firm, it might have changed ownership once or twice during those 17 years. Instead, having called Volaris home, it has benefited from steady, ongoing investment and strategic guidance, set up from the moment of acquisition and continually adjusted. Aside from maintaining its market leadership, AssetWorks has grown and deepened its expertise into specialized verticals and benefited from the decentralized leadership approach that Volaris practices.
When AssetWorks became part of Volaris, it resulted in an impressive ‘family tree’ of employees that have grown professionally with Volaris, and those who have gone on to become acquiring managers.
–Gordon Smith, Portfolio Leader, Volaris Group
AssetWorks: Investing in Leaders
The growth of its leaders has been one of the drivers of success for AssetWorks. Here are just some of the people that Volaris and AssetWorks have invested in. They have had the chance to flourish and build rewarding careers in an environment of learning and mentorship.
Several leaders who were part of the MAXIMUS acquisition are still with the company today. They include:
- Gordon Smith: Gordon joined Volaris in 2008 as part of the MAXIMUS acquisition. At MAXIMUS, he was the division’s Vice President of Product Management. Once he joined Volaris, he was promoted from COO to General Manager of AssetWorks. As he thrived in the Volaris ecosystem, he became more involved with acquisitions, and 17 years later, he is a Portfolio Leader and one of the most senior leaders within Volaris, overseeing all M&A and operational activities for a portfolio of more than 30 businesses.
- Tony DeSilvester: Like Gordon, Tony first became part of Volaris through the MAXIMUS acquisition in 2008. He started his career as an installation technician in 1998, and after AssetWorks joined Volaris, he gained exposure to sales, professional services, and general management of software businesses. As a Portfolio Leader and one of the most senior leaders at Volaris, he oversees the management of vertical market software companies and his portfolio’s M&A goals. Due to the opportunities afforded to him, he has dedicated his management career to mentoring and building leaders throughout his portfolio.
- Michael Borello: Another leader who came to Volaris from MAXIMUS in 2008, he moved into M&A after being involved in his first acquisition in 2010 while leading AssetWorks Appraisal. As a Group Leader, he oversees M&A activities for the fixed asset management software and risk management software verticals, and coaches acquired companies to grow their businesses.
- Randall Walsh: Another leader who joined Volaris through the MAXIMUS acquisition in 2008, he started as a Product Manager and moved into leadership roles in professional services and sales at AssetWorks Facilities. Under his leadership, AssetWorks facilities expanded geographically and implemented a cross-selling program. As of 2025, he is a Group Manager overseeing several businesses.
- Christian Gutierrez: After joining AssetWorks and Volaris in 2008 from MAXIMUS, Christian grew from Director of Information Services to Director of Special Projects, to VP of Product Management, to General Manager of AssetWorks’ Risk Management division, which rebranded to Centurisk in 2024.
- Rob Hallett: Rob’s career at AssetWorks Fleet has propelled him from a project manager to a leadership role in professional services, then to COO and General Manager. While leading AssetWorks Fleet, he navigated the COVID-19 pandemic by pivoting to virtual customer engagement and spearheaded the successful launch of five new products that helped sustain double-digit growth. As a Group Manager, he is focused on expanding the Asset and Fleet Management portfolio, fostering collaboration among leaders, and ensuring that newly acquired businesses are onboarded seamlessly.
- Carl Bruce: A sales executive at the time that Volaris acquired MAXIMUS, his leadership has expanded after Volaris acquired AssetWorks. As a Portfolio Manager, he is building out the securities and medical verticals within Volaris Group’s portfolio, working with Portfolio Leader Gordon Smith.
During the 17 years that AssetWorks has been part of Volaris, the company has continued to attract talent and invest in their growth. Leaders who are building careers at AssetWorks include:
- Cristina Wheless: Her history with AssetWorks began when she joined in 2017 as the Chief Services Officer. From there, she was given the opportunity to advance quickly through the organization, taking on progressively more responsibility as COO, CEO, Group Leader, and as of 2024, a Portfolio COO. As a leader, she takes pride in empowering people and developing talent within her team.
- Trey Drake: While Trey didn’t join Volaris during the acquisition, he worked at MAXIMUS before the deal happened, working in software development there between 2003-2006. He rejoined AssetWorks in 2013, after it had been under the ownership of Volaris for five years. Since then, he has taken on several leadership roles: VP of Product, COO, Group President, Group Leader, and Portfolio Manager. As of 2025, he became the AI Transformation Officer, bringing insights to the broader portfolio.
- Dean Hebert: Dean came to AssetWorks after selling InCircuit to AssetWorks in 2010. Between 2010 and 2024, he worked in operations, sales, customer success, and as a COO and CEO for the AssetWorks Asset SaaS division – eventually leading him to a role as Group Manager, where he applies his knowledge to M&A and operations.
- Ellena Howze: Ellena came to AssetWorks through the acquisition of InCircuit in 2010, where she worked on application design and development. Joining Volaris and AssetWorks broadened her opportunities, and she took on leadership roles in R&D, professional services, and operations before becoming the General Manager of AssetWorks Appraisal – Asset Management.
- Glenn Adams: Currently the General Manager of AssetWorks Facilities, he joined the company in 2013 and gained progressively more experience in product management, which later led to leadership positions as the Chief Product Officer, COO and General Manager.
- Crystal Germond: Before taking on the role of General Manager at eQuip in 2024 (part of AssetWorks), Crystal had taken on progressively senior roles in sales and marketing at the Fixed Assets division of AssetWorks since 2020.
The list of leaders who are building long-term careers at AssetWorks is continually growing, reflecting a belief that developing a strong bench of leaders gives resilience to the larger organization. It remains part of the long-term growth strategy at AssetWorks to create many career opportunities for people to move up within the organization.
I’ve always been incredibly proud of my team for growing from very small beginnings to something a lot larger. It has bound us not only to our customers, but to each other. We are a very tight knit team and it leads to collaborations across the department, making strategy a lot easier. There’s buy-in from everyone in our processes and I’m proud of that.
-Christian Gutierrez, General Manager, Centurisk
What’s next for AssetWorks
As AssetWorks continues to maintain market leadership and expand into new areas of growth, we look forward to what another 17 years will bring to them within Volaris.
