New Portside CEO on steering a growth course
Brandon Holden, Portside's new CEO, has more than two decades' experience leading high-growth businesses.
Following a recent majority investment by Vista Equity Partners, CJI sat down with Portside’s new and outgoing CEOs Brandon Holden and Alek Vernitsky to find out where the company is headed next.
Holden stepped into the role about 45 days ago, taking over from Vernitsky, who co-founded Portside alongside Alek Strygin in 2017. Vernitsky will continue to serve as a strategic advisor, focusing on product vision, AI innovation and large customer engagement, and will sit on the board of directors.
Vista initially became a minority investor in May 2024, following a $50m Series B raise led by global software investor Insight Partners in February 2023. Insight Partners is staying on as a “significant” shareholder. The new majority investment marks the start of a new growth phase for a company that now counts over 1,200 customers and 15,000 aircraft on its platform, with teams and customers spread across the globe.
Building the platform: M&A as strategy
Portside’s growth has been underpinned by a deliberate acquisition strategy. The company has made a series of aviation-focused software acquisitions — including Takeflite, LeaseWorks and Baldwin Safety and Compliance — that together have assembled a broad, integrated platform rather than a collection of point solutions.
“We’ve got an incredible platform that both helps us deeply continue to understand the end market, the problems and the customer bases that we’re trying to solve,” said Holden.
Vernitsky underscored the platform’s depth for larger customers: “At this point we can support them around the sun. We have capabilities that no other software player in the space has — in building the functionality that they need, in integrating into their technology footprint and supporting multiple lines of business, be it fractional, management, FBO or MRO.”
Growth priorities
Holden described the next chapter of growth as twofold. First, deepening value for existing customers. “How can we solve more of their problems with the technologies that we have today that they may not be taking advantage of yet?” he said. “Expanding the reach and breadth of capabilities to serve our existing customers is certainly one area.”
Second, expanding into new markets. “Continuing to expand geographically into new end markets and markets around the world where we believe, through our technology, we have a real right to win,” he added.
Alongside these two priorities, Holden highlighted a third: investing in the post-sales customer experience. “Once a customer has decided to make those investments with Portside, how can we continue to help them understand the value they are getting from our technology through an improved investment in customer success and customer support?” he said. “We’re continuing to size this and will start to invest in it pretty quickly.”
AI roadmap: from abstract to practical
Portside’s next phase is based upon what Holden describes as an “AI-enabled roadmap”, with implications both internally and externally.
Internally, the company is looking to leverage agentic AI to accelerate its own development. “In product management you get a million different signals around what customers need,” said Holden. “Leveraging agentic tooling helps us dramatically improve the pace of innovation we can deliver on behalf of our customers.”
Externally, the opportunity is to make agentic capabilities tangible for operators. Rather than displacing enterprise software, Holden believes AI is “supercharging” it. Concrete examples of where Portside is targeting agentic workflows include quoting optimisation, schedule optimisation and logistics management. “Areas where automation can meaningfully reduce the burden on schedulers, leasers and airline operators,” said Holden
“That listening tour is about understanding what challenges our customers are facing to be successful in their roles — and where we can accelerate our own roadmap to solve their problems quicker through agentic capabilities,” he added.
What customers can expect
Customers can expect three immediate areas of investment as a result of the Vista majority stake, said Holden. First, significant commitment to core products and technologies, second, a deeper agentic AI capabilities embedded in existing workflows, and lastly a materially improved customer experience post-sale.
“We are looking at how our end customers are leveraging the technology today and where we can double down and continue to invest in the core technologies that are super strategic to our long-term success,” said Holden.
Founder transition: Vernitsky’s next chapter
Vernitsky’s move to a strategic advisor role is less a step back than a deliberate refocus on where he has the most impact. He will work closely with Portside’s largest customers — those with the most complex, multi-solution needs.
Alek Vernitsky co-founded Portside alongside Alek Strygin in 2017.
“Where I’m going to focus is the larger customers who have very complex needs, who frequently need multiple software solutions and a complex implementation,” he explained.
For Vernitsky, the arrival of Holden as CEO and Christopher Johnson as incoming chief operating officer represents a natural evolution. “Bringing in a professional management team makes a huge difference in helping Portside scale,” he said. “It is really exciting to have Brandon and Christopher joining, both with vast experience scaling enterprise businesses and working with large private equity funds.”
Holden, who has more than two decades’ experience leading high-growth businesses, said what drew him to Portside was the strength of its founders and the quality of its customer base. “When you really look under the hood at how our customers are using and leveraging our technology, they are addressing and solving some of their most mission-critical challenges,” he said. “A world-class customer base, a growing TAM, a growing market and the opportunity to partner with those existing customers — that’s what attracted me personally to the role.”
