HubSpot is flailing. Again.
On Thursday, the Boston-based CX platform company replaced CEO, president and board member Yamini Rangan with former CEO and co-founder Brian Halligan, who had been CEO until 2021. Rangan stepped down as CEO and left the board effective Nov. 12, but will remain with HubSpot through Dec. 1 to assist with the transition.
Only Halligan — the serially ebullient pitchman — could frame the executive shuffle as a "refounding," as the returning CEO termed it on X. He also rechristened HubSpot a "customer relationship harness" company.
The company also said that Karen Burgess, current Adobe SVP and CFO of its Creativity & Productivity Business, will take over as HubSpot's next CFO, replacing current CFO Kate Bueker — who is retiring — on February 11, 2027.
Ostensibly, the executive refresh is an attempt to right the Good Ship HubSpot, whose stock jumped more than 6% Thursday on the news. Overall, the stock has lost about 50% of its value so far in 2026 — continuing a precipitous fall that began in early 2025. Thursday's gain might look good on paper, but it wasn't enough to recover what the stock had lost just last week following a disappointing fourth-quarter revenue outlook.
The CEO merry-go-round is just the latest HubSpot dumpster fire. A few other greatest hits:
- HubSpot co-founder and CTO Dharmesh Shah apologized last month for writing what he termed a "curt and insensitive" LinkedIn post about nearly 660 employees affected by HubSpot's October restructuring — about 7% of its workforce.
- An abrupt reversal last summer after HubSpot proposed changes to its terms of service that would have allowed it to use business contact information in a shared data-enrichment product offered to other customers. The resulting mea culpa made for great tech-vendor theater.
- In May, a whistleblower filed a lawsuit alleging retaliation. He had been put on a performance improvement plan after returning from parental leave. He later reported a data privacy bug affecting more than 67,000 customer accounts, according to Human Resources Director. The case is ongoing.
- There have been other controversies over the years. Let's not forget the granddaddy of them all: the 2015 attempt by HubSpot executives to obtain a prepublication version of Disrupted, the tell-all book authored by former Newsweek tech editor Dan Lyons, who worked briefly for HubSpot and went on to write for the television comedy show Silicon Valley. HubSpot's board fined Halligan for failing to promptly report what he knew, but found he wasn't involved in the attempt. Federal authorities investigated but brought no charges.
HubSpot hasn't announced a rebranding of Unbound back to Inbound — but if they can bring back their old CEO, one would think the idea could at least be on the table.
All of the above doesn't take into account the peculiar renaming of the beloved-by-customers Inbound conference to "Unbound" earlier this year.
It was almost an admission of defeat. HubSpot had built its legacy on "inbound marketing," its concept of attracting customers with sticky content instead of pushing intrusive outbound messages. "Unbound," ostensibly, took into account the idea that customer journeys are no longer linear and are AI-driven. It's a New Coke-Coke Classic thing, when a reformulation of the iconic American soft drink lasted just 79 days.
HubSpot hasn't announced a rebranding of Unbound back to Inbound — but if they can bring back their old CEO, one would think the idea could at least be on the table.
And can we talk a second about the CEO shuffle the company slipped under the radar as the story of Jensen Huang's ouster from Nvidia dominated the tech news cycle this week? While we may never know the true reasons behind the timing of HubSpot's announcement, a PR person at a competing vendor called it "smart."
Here's the silver lining
All that said, HubSpot had made a strong hire with Rangan, formerly of Workday and Dropbox. She radiated stability and confidence as she ushered HubSpot out of the Disrupted years and into the world of generative and agentic AI, not to mention a bold experiment in outcomes-based pricing that has yet to be fully written.
But that epoch has ended. Time to take stock of what remains.
"The company must demonstrate that its new AI agents deliver clear, measurable ROI so customers willingly pay for usage credits rather than feeling nickel-and-dimed."
Predrag Jakovljevic
Technology Evaluation Centers
On the plus side, HubSpot has built a loyal base of ride-or-die customers, the number of which increased from 135,000 to 311,000 during Rangan's tenure as CEO. She presided over annual revenue growth from $1.3 billion to an estimated $3.7 billion in 2026, according to the company.
While the hyper-recent financials and the long track record of public-relations stumbles might appear to show a company in decline, analyst Predrag Jakovljevic of Technology Evaluation Centers points out that the company remains profitable and generates strong cash flow.
HubSpot has to get its reorientation around customer outcomes — which extends to both product teams and pricing — right, Jakovljevic said.
"HubSpot's core small-and-midsize business base is price-sensitive," he said. "The company must demonstrate that its new AI agents deliver clear, measurable ROI so customers willingly pay for usage credits rather than feeling nickel-and-dimed.”
Despite HubSpot's focus on smaller businesses, Jakovljevic said its pricing can resemble that of enterprise CRM platforms.
The other thing HubSpot must maintain through its transition is a quality experience for its customers.
"Shedding 7% of the workforce — and switching CEOs and CFOs simultaneously — [could] cause temporary hiccups in account management and customer support responsiveness," Jakovljevic said. "Stabilizing engineering and go-to-market teams quickly is essential so product quality does not suffer during the transition."
If HubSpot can get all that right, it might pull through this latest crisis of Wall Street confidence. If you think that might happen — and the company will stop flailing — you can take your smart money to Polymarket and bet on the next quarter's earnings. I'm just here to watch the fireworks, myself.
Don Fluckinger is a seasoned B2B technology journalist with more than 30 years of experience specializing in enterprise IT, digital experience and content management. As a senior news writer at Informa TechTarget, he delivers award-winning analysis that helps IT and business leaders navigate complex technologies to enhance customer and employee experiences. Got a tip? Email him.
