Buying a business gives a chief executive something satisfying to announce. Selling parts of it requires a longer explanation. Jack McDonald has spent much of his career on the first side of that equation. As his time running Upland Software drew to a close, the second side became harder to ignore. The company he had assembled was getting smaller, its priorities more concentrated, and the job at the top was changing with it.
On May 1, 2026, Sean Nathaniel became Upland’s chief executive. McDonald, its founder and CEO since July 2010, continued as chairman. A succession announcement can make such a change sound like a matter of moving names around an organizational chart. This one followed a more substantial rearrangement: an acquisition business had been selling assets and directing attention toward its remaining software.
The interesting question in McDonald’s career is what happens after the deal. His experience stretches from corporate law to information technology consulting to enterprise applications. Across those settings, he has repeatedly faced the same practical problem: once the transaction is finished, somebody has to make the business work.
A lawyer learns to live with the deal
McDonald studied economics at Fordham University and earned his law degree at Fordham Law School. From 1987 to 1993, he worked at Skadden, Arps, Slate, Meagher & Flom in New York, concentrating on mergers and acquisitions and corporate finance. It was an education in how companies change hands, how capital is arranged, and how the promises in a transaction become obligations.
Running a company made those obligations his own. He became Perficient’s CEO in 1999 and served in that position through 2009. He also chaired the company from 2001 to 2010. The distinction matters: his later association with software acquisitions followed a decade of responsibility for a consulting business, where delivering work to customers was the daily assignment.
That decade contained some distinctly unglamorous arithmetic. In the third quarter of 2001, Perficient recorded a $27 million goodwill impairment, largely connected with its earlier acquisition of Compete. The technology downturn had changed valuations. A price once supported by the market now had to be reconsidered on the balance sheet. The paperwork had a long memory.
McDonald continued to pursue acquisitions during the downturn, including the pending Vertecon transaction. The company was also doing technology and consulting work for customers including Chevron and Toronto Dominion Bank. Growth ambitions and the need to keep serving existing clients occupied the same desk.
By the first quarter of 2007, the picture had changed. Perficient reported 69 percent year-over-year growth in services revenue, had acquired E-Tech Solutions, and entered the next quarter with an annualized revenue run rate above $200 million. Its debt stood at $2.9 million after the acquisition and year-end bonuses. Scale had become something visible in operating results, alongside the continuing appetite for deals.
The arc helps explain why acquisition and execution remained linked in McDonald’s next venture. A purchased business brings revenue, but also employees, customers, expectations and a history. The purchase agreement does remarkably little of their work for them.
First Silverback, then Upland
The company that became Upland began in July 2010 as Silverback Acquisition Corporation. It became Silverback Enterprise Group in September 2011, then Upland Software in November 2013. The sequence of names is a useful little history of its own: a vehicle for acquisitions gradually acquired the identity under which customers and investors would come to know it.
Upland completed its IPO in November 2014. In the run-up to the offering, it had booked $54 million in sales over the twelve months ending June 30. McDonald and finance chief Michael Hill had both held senior roles at Perficient. The new public company carried an established working relationship into a different part of the technology market.
The acquisitions kept arriving. Later that November, Upland bought Toronto-based Solution Q for about $5.8 million. Its Eclipse application added project and portfolio management software for midsize organizations. Upland planned to retain the acquired company’s employees and management. The announcement described a product with a particular job and an existing audience.
In December came Brooklyn’s Mobile Commons, for approximately $5.1 million. Its text messaging tools served advocacy, fundraising and other forms of engagement. The co-founders would remain in leadership roles, and the product would continue as a standalone offering while connecting with parts of Upland’s existing portfolio. It was the eighth acquisition in three years.
Read together, the purchases show the appeal and the management burden of McDonald’s approach. Instead of waiting for one application to become everything, Upland could acquire products already doing useful work. Each addition also enlarged the list of things the company had to understand and support.
The pleasure, and the paperwork, of scale
By the third quarter of 2018, Upland reported revenue of $37.1 million, up 42 percent from a year earlier. Adjusted EBITDA reached $13.1 million, or 35 percent of revenue. It also recorded a GAAP net loss of $4.3 million. Those figures describe different aspects of the same business; the adjusted operating measure did not erase the accounting loss.
Just after the quarter ended, Upland acquired Rant & Rave, adding customer and employee feedback tools. The product portfolio was spreading across the ways organizations managed work and communicated with people. For McDonald, the question of what belonged together was becoming as significant as the question of what could be bought.
“You have to be bold but you have to be realistic.”
Jack McDonald · 2019
His stated leadership preference was ambition that could survive contact with execution. He recommended William Thorndike’s The Outsiders, a book about chief executives and capital allocation. He also described spending years establishing a common operating model, Upland One, after initially running acquired products as separate companies. The mechanics of integration had become a substantial part of his own job.
His responsibilities extended into Austin’s business community. He chaired the Greater Austin Chamber of Commerce in 2014. Later, he joined BigCommerce’s board, serving from 2019 to 2022. These were settings in which the software executive also worked as a director and civic business leader, outside the company he had founded.
At the end of 2020, the acquisition logic was still central. Upland reported 31 percent total revenue growth for the year. McDonald described a buying range focused on software businesses with roughly $5 million to $25 million in revenue, emphasizing established enterprise customers and applications customers tended to keep. The attraction was specific: a useful product could arrive with a durable commercial relationship attached.
He also described an acquisition program supported by Upland’s cash generation and financial resources, reducing dependence on equity markets. That was the capital allocator’s recurring concern. An attractive target is only part of the calculation. The money used to buy it has a cost and a set of consequences too.
Then the buyer became an editor
By 2025, McDonald was explaining a narrower focus. In May, he pointed to concentrating on products with stronger competitive positions, growth and margins. He also discussed centralized digital marketing and a development center in India. The route forward involved making the retained products sell and perform better.
One example gave that argument some texture. He described a sale worth more than $500,000 in annual recurring revenue to a major technology company working on an enterprise language-model implementation for customer support. Upland’s RightAnswers supplied knowledge-management capabilities relevant to that work. The customer was unnamed, but the commercial idea was concrete: software organizing reliable information could have a role in an AI project.
The year-end numbers made the portfolio changes visible. Fourth-quarter 2025 revenue was $49.3 million, down 28 percent, primarily because of divestitures completed in the first half of the year. Adjusted EBITDA was $15.3 million, or 31 percent of revenue, compared with a 22 percent margin a year earlier. Annual free cash flow reached $24.4 million.
Those results give the succession its context. A smaller revenue base and a higher adjusted margin were consequences of choices about the portfolio. The operating question had become how to develop the remaining business. Another acquisition could no longer serve as the automatic next sentence.
A different assignment at the top
Nathaniel was familiar with the company he returned to lead. He had worked at Upland from 2013 to 2020, including as chief technology officer, and had been on the executive team during the 2014 IPO. Before returning, he led DryvIQ, which worked on AI-driven management of unstructured data. His experience matched the direction Upland was emphasizing.
On the March 2026 earnings call, an analyst asked McDonald why he was stepping down. His explanation centered on the business having changed. Earlier, acquisitions had driven growth; the assignment now leaned toward operations and advancing AI-enabled products. He wanted a leader whose background fitted that assignment.
He was also candid about the work still ahead. Fourth-quarter bookings had disappointed him. Some products had opportunities in the changing market; others faced pressure. Before the handoff, Upland had sold assets and refinanced debt. He described wanting to leave the incoming CEO a business on firmer footing.
McDonald remained chairman. The continuation suits a career spent examining companies from several angles: lawyer, buyer, operator, director. His Upland story now includes the decision to change his own place in it. After years of adding businesses, he had reached a judgment about what the company needed next, and who should do the work.