Our panelists shared how succession planning creates a strategic advantage for founders and business owners looking to exit

Did you miss the webinar? Watch the replay and review key takeaways below.

Many software business owners and founders only put their attention on succession planning once they are eyeing retirement, a sale, or a next chapter.

But thinking several years ahead is more likely to result in the best outcomes for everyone, including customers, employees, and the leaders who is looking to move on.

As a buy-and-hold acquirer of software businesses, we shared our long-term approach to succession planning in a webinar called “Turning Succession Planning into a Strategic Advantage,” which ran live on October 28, 2026.

Three leaders from across the Volaris Group network joined Chief of Staff Ryan Hill to share their experiences. Each of them has previously stepped into a leadership role at a business for the first time after being acquired by Volaris, and each later handed a business to a successor. The leaders were:

• Kevin Bradley, CEO of Vencora, joined Wellington IT as a sales executive in 2003 and became Managing Director when the founders sold the company to Volaris in 2014.
• Andy Nelson, Portfolio Leader at Omegro, was a British Army officer before joining Wellington IT as a developer. He became the first managing director of Gaina, a drinks industry software business that was split out of Wellington IT, another company acquired by Volaris. He later handed the leadership title at Gaina to another Volaris leader, Kealan Curran.
• Ian Glenn, Group Leader at Vencora, went from leading development at Wellington IT to becoming CTO and then CEO in fewer than four years. In 2025, he handed the business to another Volaris leader, Colin Mitchell.

Together, the panelists have seen succession from every side. Here are five takeaways from their discussion for software business leaders who are thinking about their next step.

1. A strong bench gives business owners more options for an exit

For company owners and founders who are thinking about retiring or selling, the options ahead of them are shaped by the strength of their senior leadership team.

“If you’ve built a management or leadership team around you, that gives you options,” said Kevin Bradley. “[A strong succession plan] makes the business more attractive to a buyer, and it gives the founder more choice about what they do next.”

His advice to business owners is to start the conversation about succession planning before there is an immediate need, instead of waiting for the “perfect moment.” Starting early makes it possible to assess where the team is today, and what it will take to get successors and senior leadership teams where they need to be to run the business.

When selling to an experienced buyer of software businesses like Volaris Group, we can help get a team ready by connecting senior leaders with coaches and a support network to help leaders as they step into new responsibilities.

2. Succession planning is a byproduct of developing talent in the business

When founders talk about succession, they often start with a revenue milestone or their own timeline. Less frequently, the conversations start with the team behind the business—but in our panel’s view, this is one of the key pieces of a smooth transition.

Their perspective is that succession works best when people are being developed every day while the business is already operating, not when succession is treated as a separate project.

Ian urged founders not to think about succession in terms of one person or one named role, which he says “puts unnecessary pressure on everyone.” Instead, he suggested looking at the capabilities that people have and what the business needs, then giving people chances to build them: an important project, a customer initiative, or work in a function they don’t know yet.

“If you build [talent development] into how you run the business day to day, and develop capability through work people are already doing, succession becomes the output.”
— Ian Glenn, Group Leader, Vencora

Panelists advocate that business owners give their senior leadership team “stretch assignments”—responsibilities that sit just beyond their current job scope—to challenge people to strengthen the business today while creating options for later.

Selling a business to the right acquirer can also open doors for the people within the business. The panelists talked about how at Volaris Group, all three of them grew into roles that went beyond the businesses that they were originally in. In Andy’s case, he benefited from Wellington IT splitting part of its business off to create Gaina. That move created a new leadership role for him and opportunities for others.

3. Plan the handover so it feels like an evolution, not an upheaval

Ideally, a leadership change should feel like a smooth and natural transition for customers or staff. Andy Nelson and Ian Glenn made sure their successors were already familiar and trusted before any announcement.

At Wellington IT, where credit union customers rely on mission-critical software, Ian put his successor, Colin Mitchell, into a customer-facing service delivery role and gave him a project to improve customer service.

“When the transition happened, Colin wasn’t introduced as a new leader customers had to get used to,” Ian said. “They already knew him and had worked with him.” Ian stayed in the background to support him, so the change was, in his words, “evolutionary rather than revolutionary.”

Andy took a similar approach at Gaina. He started with assigning his successor to run meetings and take on management team work, which showed staff that the business, and their own roles, would be in good hands. Then they turned to customers, with Kealan handling escalations that Andy would otherwise have taken.

As a result, the eventual transition went so smoothly that he joked: “I’m not sure anybody noticed I’d gone.” What people did notice was a business moving forward quickly under its new leader, with new products, new geographies and new sales efforts. When the change was announced, it was obvious to the team that it was the right thing to do.

4. Avoid common mistakes when naming a successor

When the panel was asked how succession can go wrong, Kevin Bradley emphasized that timing in naming a successor needs to be carefully considered. Common mistakes related to the decision are:

• Naming someone too soon. If a candidate has been named before the stretch assignments have been given, the business owner can risk backing themselves into a corner if the assignments don’t go well.
• Starting a clock you can’t keep. “When you tell someone they could have a future role, you start a clock,” Kevin said. If 12 or 18 months pass with nothing happening, the person may become jaded and assume there has been a change of heart.
• Leaving the question of a successor open for too long. When everyone can see a successor is needed but nobody knows who it will be, the result can be competition, infighting and turnover in the team.
  

The panel’s answer to avoiding these mistakes is to keep career conversations open and ongoing, have the conversations early, and to communicate once there’s alignment, a clear candidate, and a realistic timeline.

5. Succession is a transition for the incoming leader as much as the outgoing one

Succession can be framed around the leader who is stepping away, but the person stepping up is also going through a major transition. The panel focused on the people dynamics of a leadership transition, and what the incoming and outgoing leaders owe each other:

• For the new leader, it can be a lonely seat. When Kevin took over Wellington IT, one of its two co-founders told him he worried Kevin would be in “a very lonely seat.” The founders had always had each other to talk through hard decisions. Luckily, Kevin found support in the wider Volaris network, among peers who had been through the same transition. Andy, recalling the concept of the “loneliness of command” from his military background, said business leaders can have some of their most useful conversations with peers who know the risks and pitfalls.
• The job itself changes. Ian described his “eureka moment” as realizing that being a good leader doesn’t mean having all the answers. He had to evolve from being the engineer who solves problems to someone who creates a safe space and enables others to succeed, including in functions he didn’t know well.
• Confidence comes from evidence. To help incoming leaders overcome impostor syndrome, Andy suggested giving them chances to prove themselves before they take the role, so they have a bank of experiences and successes to draw on. Kevin added that new leaders need clarity on where to spend their time, plus a few early wins, so they aren’t tempted to retreat to their old functional area.
• For the outgoing leader, the job is to step back. As moderator Ryan Hill noted, moving on from the leadership role has to be an ego-free decision. When people keep coming to an outgoing leader out of habit, Kevin advises sending them to the new leader: “Don’t undermine them in the new role. Endorse them, and if you disagree, have a quiet word in private.”

Actionable steps that business owners can take

To close the webinar, each panelist suggested one step that leaders can take within 30 days to get started in the succession process:

• Hand over a meaningful responsibility. “Pick one meaningful thing you’d normally do yourself, find someone in your organization, and give them real ownership of it,” Ian said. “Resist the urge to take it back.” This step will help a business owner learn what their people are capable of, and how much the owner or founder is capable of letting go.
• Find your single points of failure. Andy suggested identifying the roles, tasks, or relationships the business couldn’t operate without. These are the places where business owners can start building redundancy and are a good source of ideas for stretch goals.
• Ask your team what they want. “It’s easy to assume you know what people want to do next without asking,” Kevin said. Talk to your people about how they’d like their careers to progress, without overpromising roles before you know your timeline.

In closing, succession planning doesn’t have to start with a deadline or a deal. As this panel showed, a successful leadership transition starts with developing the people within the business, and the options it creates are worth having, whatever you decide to do next.