Another month, another restructuring with artificial intelligence somewhere in the explanation. In early October 2026, software company HubSpot announced it would cut about 660 positions, roughly 7% of its global workforce, as part of a plan tied to what it calls a shift toward AI-driven customer outcomes, Quartz reported.
What makes HubSpot's case worth a closer look isn't the size of the cut. It's how the company explained it. Its chief executive said the move wasn't driven by AI replacing workers. It was about reorganising the company for a world AI has already changed. That distinction says a lot about how many organisations are thinking right now.
What HubSpot announced
- About 660 roles eliminated, roughly 7% of staff, with the plan authorised by the board on 1 October 2026.
- Expected charges of $65 million to $75 million, mostly severance and transition costs, largely in the fourth quarter.
- Reductions to be completed no later than the end of the first quarter of 2027.
- Revenue and profit guidance for 2026 reaffirmed.
Chief executive Yamini Rangan wrote to employees that the AI shift "is transforming product, pricing and how we serve our customers", adding: "But we also need to fundamentally change the way we are organized to compete and win." She said the aim was a flatter organisation with fewer management layers, moving decisions closer to the people doing the work.
According to the Boston Globe, as cited by Quartz, the severance package includes a minimum of 20 weeks of base pay, laptop retention and job-search support.
A wider pattern
HubSpot isn't alone. Quartz noted that AI-cited job cuts reached 38,579 in May 2026 alone, the highest monthly total since outplacement firm Challenger, Gray & Christmas began tracking the category in 2023. It also noted that some companies have reversed AI-driven layoffs after finding the technology couldn't fully replace the roles they'd cut.
Three forces seem to be driving these restructurings:
1. Customers expect different things
When AI changes what a product can do, it changes what customers pay for. Companies selling software, services or support are rethinking pricing and delivery, and with them the teams behind each.
2. Fewer layers, faster decisions
The push for "flatter" organisations isn't new, but AI tools that summarise, report and coordinate work make some layers of oversight feel less necessary. Many leaders want decisions made closer to customers.
3. Investor pressure
Quartz reported that HubSpot's shares had fallen roughly 45% since the start of the year. Public companies facing that kind of pressure are expected to show they can adapt quickly and protect margins.
The lesson from 2026 so far: cutting people because you expect AI to do their jobs is risky. Reorganising around how AI changes your customers is a different, and more defensible, decision.
Lessons for business leaders
- Be honest about the reason. Staff and customers can tell the difference between "AI replaced you" and "our business model is changing". Say which one applies, and mean it.
- Test before you cut. The companies that reversed AI-driven layoffs learned the hard way. Run pilots to show that new tools can actually handle the work before you remove the people doing it.
- Flatten thoughtfully. Removing managers can speed decisions, but it can also overload those who remain and remove mentoring. Redesign roles and responsibilities, not just the org chart.
- Treat departing staff well. Generous severance, practical support and clear communication protect your reputation with remaining employees, future hires and customers.
- Invest in the people who stay. Training in new tools and workflows is what turns a restructuring into a real change in capability.
What good restructuring communication looks like
How a restructuring is announced shapes how it's remembered. The better examples tend to share a few traits: the people affected hear first, and directly, rather than through the press; the business reasoning is explained in plain language; support for departing staff is specific rather than vague; and remaining employees are told clearly what changes for them and what does not. HubSpot's decision to set out a minimum severance figure and reaffirm its financial guidance at the same time is an example of giving both employees and investors concrete information rather than leaving a vacuum for rumours to fill.
Advice for employees
- Get fluent in your tools. People who use AI to do better work are more valuable than those who either ignore it or lean on it blindly.
- Move closer to the customer. Roles that directly create outcomes for customers tend to survive reorganisations best.
- Document your impact. Keep a running record of results you've delivered. It helps in reviews, internal moves and job searches.
- Keep a financial buffer. An emergency fund turns a layoff from a crisis into a manageable transition.
- Stay connected. Your network outside your company is your best insurance in a fast-changing job market.
Signals to watch in your own organisation
Restructurings rarely come out of nowhere. Common early signs include sustained pressure on the share price or funding, leadership talking about "new operating models", hiring freezes in particular functions and big investments in automation tools. None of these guarantees cuts, but they're a good prompt to update your CV and have an honest conversation with your manager about where your role fits.
The bottom line
HubSpot's restructuring is part of a broader rethink of how companies organise for an AI-shaped economy. The organisations most likely to come out ahead are the ones that cut carefully and honestly, prove new ways of working before betting on them and invest in the people who remain. For workers, the best protection is to stay close to the value you create and keep learning the tools that are reshaping your field.
