• Website-building company Squarespace is laying off 19% of staff.
• In a memo, CEO Anthony Casalena said most of the cuts affect product and engineering teams.
• Casalena added that the changes would mean “more player coaches.”

Squarespace is laying off 19% of its staff in a move its CEO said would help it “adapt for the modern era” with leaner teams and “more player coaches.”

The website-building software company is reducing its head count by about 300 employees, according to a companywide memo sent by Squarespace CEO Anthony Casalena on Monday.

Most of the cuts affect product and engineering teams, according to the memo, which was seen by Business Insider.

“The way we need to work is changing faster than at any point in our history, and our operating model must adapt for the modern era,” wrote Casalena. “This means smaller teams, more player coaches, and a simplified organizational structure.”

Affected staff will get a minimum of 16 weeks of base salary plus additional weeks based on tenure and benefits through May 2027. Employees would also be able to keep their company laptops, and those on work visas would get continued support, the memo said.

A spokesperson confirmed the layoffs and memo to Business Insider, adding: “The changes are intended to simplify how we operate, sharpen our priorities and enable the company to move faster as we position Squarespace for its next phase of growth.”

Later on Monday, Casalena hosted a livestream presentation about the layoffs for remaining employees. He reiterated the points made in his memo during the roughly one-minute livestream, which did not allow for comments. The company is planning a separate all-hands meeting, the spokesperson said.

The cuts, first reported by The Verge, come after Squarespace has increasingly added AI features to its products.

Squarespace joins a long list of companies that have laid off staff this year, some of which have cited the rise in AI. Last week, Microsoft offered buyouts to 60,000 employees, though the company told Business Insider it expects only 3,000 or fewer to take the offer.

Casalena also joins a list of CEOs who have cited leaner teams when discussing layoffs — in February, Block CEO Jack Dorsey emphasized a shift toward smaller teams in a post on X about cutting his company nearly in half.

Read the Squarespace CEO’s memo to staff:

All —

I am writing today to announce one of the most difficult decisions I’ve had to make in the history of our company. We will be reducing our workforce by ~19% and saying goodbye to around 300 of our colleagues, with most of these reductions affecting Product & Engineering. Within the next twenty minutes, impacted US employees will receive an email and personal meeting invitation and potentially impacted non-US employees will receive country-specific details.

This is not a decision I arrived at lightly, and I’d like to explain why it was made and what we will be doing for those leaving Squarespace.

The way we need to work is changing faster than at any point in our history, and our operating model must adapt for the modern era. This means smaller teams, more player coaches, and a simplified organizational structure. This is not an exercise designed to reach a financial target — it is about reshaping our organization around how we need to work going forward.

Squarespace’s core business has been about empowering people to establish themselves online in a world where technology was a major barrier. Technology still is a major barrier for many, but it has changed in ways we could not have anticipated before the past 12 months. Our product and industry is undergoing a fundamental change, and our organization must too.

Those who will be leaving us have been an important part of getting us to where we are today, and I’m grateful for their contributions. To support their transition, we will be offering*:

• A minimum of 16 weeks of base salary, plus additional weeks based on tenure
• Payment of the November 20, 2026 vesting of the legacy RSU cash award, where applicable
• Continuation of benefits through May 2027
• Career coaching, resume preparation, and job search assistance
• Additional support for employees on work visas
• Impacted employees may keep their Squarespace laptops

To those staying, your department leaders will reach out to ensure you understand the changes specific to you and your teams and that you have the direction and support you need to work through them. We will also have a brief livestream presentation later today, which will be added to calendars shortly.

After we have had time to absorb today’s changes, we will come back together to talk about the opportunity ahead of us. Today, however, I want to say thank you to those who have been a part of this journey with us. Whether staying or leaving, I understand this decision will impact all of you emotionally. I would encourage everyone to take some time to reset and digest as we move forward.

Anthony

(Outside the US, we will communicate further with you, follow local processes and, where applicable, seek to provide comparable support.)

• John Deere’s AI assistant, unveiled in September, helps farmers analyze data quickly.
• JD is embedded in John Deere’s Operations Center, a digital farm management system.
• Farmers are warming to AI, but accuracy and data privacy remain concerns.

Farmers have more data than ever about their fields, equipment, and crops. But turning it into a decision could take weeks.

John Deere says its new AI assistant, JD, can do it in minutes.

The agricultural manufacturing company announced the tool in September at the Farm Progress Show in Iowa. JD is integrated within John Deere’s Operations Center, which is a digital farm management system that connects farmers’ field and machine data into one platform. Farmers can ask JD questions on their mobile devices, such as the best time to harvest based on past trends, or which sprayer covers the most acres per hour.

Melissa Neuendorf, the principal product manager for customer AI solutions at John Deere, told Business Insider that JD came about because farmers consistently said they were struggling to manage their abundant data.

“We’re now at a point where farmers have so much data that they have a difficult time finding the insights manually themselves,” Neuendorf said.

While smaller agricultural tech companies such as OneSoil, VisorPro, Arable, and AgZen are developing generative AI tools to give insights on specific equipment or crop metrics, Deere is among the first major agricultural-equipment makers to put a large language model AI assistant directly inside a platform that combines farmers’ field, machine, and operational data. JD’s launch shows how generative AI is becoming a central part of crop management.

“Prior to John Deere’s announcement, this didn’t exist in the industry,” said Matt Darr, a professor in the agricultural and biosystems engineering department at Iowa State University, who was in the room when Deere announced JD.

Why farmers are considering AI tools more than ever

Farmers have been collecting data for decades. But now, modern farm equipment is outfitted with additional technology and sensors, creating large volumes of data that are difficult to keep up with.

It can be stressful for farmers who must also navigate tight margins, unpredictable weather, and limited planting windows. Plus, “most farmers aren’t data scientists on the side,” Darr said.

Neuendorf said dissecting vast datasets is complex and time-consuming, sometimes requiring weeks. That’s where AI can help farmers: “AI provides them the capability to do a lot of that analysis in minutes,” she said.

Before coming up with JD, Deere launched an AI tool last August that allowed farmers to ask questions in natural language about Deere’s help documentation and operator manuals. This replaced the manual task of farmers flipping through pages of operator manuals.

The tool received positive feedback, prompting Deere to broaden its application and launch JD to answer specific questions on the spot.

Farmers can input data into the Operations Center from non-John Deere equipment if they use machinery from other manufacturers. Then, if they query JD, it can analyze all of that data to deliver answers.

The Operations Center and JD are free to use, Neuendorf said. The AI assistant is available through an early access program, in which interested customers sign up for a waitlist and are considered for participation. John Deere will make JD broadly available in mid-November

Neuendorf told Business Insider that the feedback from farmers so far has been positive.

Neuendorf said she recently spoke to a farmer who was driving past a field and noticed it had lower weed pressure, or fewer weeds present, than other fields. Through JD, the farmer was able to open John Deere’s mobile app right away, ask the assistant about previous years, and understand how he managed the field differently.

Winning farmer trust in AI technology

A McKinsey global survey of 5,500 farmers, published in September, found that 72% expect generative AI to impact operations within five years, but only 17% use the tech right now.

One reason only a minority of farmers use AI is because they’re worried about data privacy and how their information could impact commodity prices, Darr said.

“These are competitive businesses,” Darr added. “How information is used can influence global markets and what happens to global commodity pricing.”

John Deere said in its release announcing JD that it doesn’t sell farm data or use it for agriculture commodity trading or speculation.

Katya Kheistver, the chief product and operating officer of OneSoil, an agricultural technology company, said farmers won’t trust AI if it delivers generic advice rather than insights tied to specific, real field data. Farmers often start their use of AI by checking the tech’s outputs against what they already know. The farmer “watches whether the answer lines up with reality,” and if it does so consistently, trust grows, Kheistver said.

The stakes are high if farmers make decisions based on AI-generated answers because they have “one chance a year to grow a crop,” Darr said. They need to be able to trust that an AI tool is accurate.

JD meshes high-quality datasets with advanced LLMs, Darr added, which sets the AI tool apart and promises a high degree of accuracy.

Neuendorf said JD is configured to notify farmers when field data is missing, rather than making inaccurate assumptions or generating false advice.

This configuration also encourages farmers to input additional data, so JD can derive more insights and help farmers “make better decisions for the next season,” Neuendorf said.

• David Heinemeier Hansson said that AI agents will bring hard times for “cantankerous” engineers.
• “Best learn some basic people skills,” Hansson wrote.
• Engineers on X chimed in to wave goodbye to engineers with bad attitudes.

Don’t be cantankerous.

David Heinemeier Hansson has some advice for engineers as they adjust to AI. Often referred to as DHH, Hansson created the webapp framework Ruby on Rails and has fashioned himself into a software sage.

On Monday, Hansson shared his prediction on X: “The age of agents is going to be amazing for most programmers, but it’ll be hard times for the cantankerous ones.”

Hansson wrote that special abilities won’t save those who are difficult to work with. That would be a dramatic shift in software engineering, where some so-called “cracked” coders can get away with large egos or social awkwardness.

“Best learn some basic people skills,” Hansson wrote.

The prediction sparked a conversation among engineers about their social habits and professionalism. One pointed out the irony: agents “don’t care how cantankerous you are,” but your human coworkers do.

One user wrote a eulogy to the “guy whose whole job security was ‘only I know how this works.'”

Dart cofounder Zack Swafford wrote that teams only tolerated bad attitudes because the staffers had “arcane tribal knowledge.”

Others questioned how new the change was. People skills have long been valuable, from networking your way into a job to landing that big promotion.

“Been true in every company forever,” one X user commented. “Skills get you hired, being easy to work with keeps you around. Agents just make it obvious faster.”

Hansson is committed to the future of AI coding. In September, he declared “pencils down” on handwritten code. Hansson explained that writing code was an “exceptional state,” performed only when something went wrong with the AI-generated code.

For some engineers, Hansson’s post was a vocabulary lesson. “I had to search the definition of ‘cantankerous,'” one engineer commented. “First time reading that word.”

For the record: cantankerous means bad-tempered and uncooperative.

• As AI remakes the field of math, some students say they feel like giving up.
• In a survey, nearly 76% of students said they were unlikely to seek careers in math academia.
• Many respondents also bristled at academic leadership.

Frontier AI programs can now do math better than graduate students.

Those students, it turns out, aren’t taking the news well.

In a paper published this week, researchers at MIT found that a vast majority of grad students and postdoctoral scholars they polled see their career prospects rapidly dimming as AI remakes the field.

Nearly 76% said they are increasingly unlikely to stay in academic math after earning their degrees. 76% said they feel less motivated to do research “as a result of AI developments.”

And in a free-response portion of the survey, grad students laid bare their raw, pent-up feelings about the subject.

Perhaps most striking is a red-hot frustration with academic leadership, which respondents described as alternatively wayward, useless, meek, silent, and ineffectual.

“It’d be great if institutes gave guidance instead of platitudes on this subject,” one respondent wrote.

“We are lacking high-level leadership from across the academic community,” another said.

For the survey, conducted by three MIT-affiliated math students, the researchers polled 268 early-career mathematicians via a Google Form. Questions were multiple-choice and free response. They all centered on AI’s ever-expanding ability to do work they’ve spent years studying.

Notably, the response window closed just after OpenAI released hundreds of solutions to long-standing problems on October 6. The authors caveated the survey, saying it represents the vibe at “only a small window of time.”

“The past couple of months have been exhausting,” the researchers wrote. “We’re being forced to reckon with existential questions about a field we love, all while incredibly uncertain about our own futures.”

Since OpenAI first really broke onto the mathematics scene in September, when it published solutions to the Navier-Stokes Millennium Prize question, the AI-generated solutions have only kept coming.

Mathematicians have described going through stages of disbelief, shock, denial, anger, and, for some, acceptance.

Though some high-level mathematical councils have convened to issue edicts on how AI should be used, it’s not like OpenAI has to listen to them.

OpenAI and Anthropic have, however, made some concessions to the math community. Both AI giants pledged a combined $15 million to a foundation to support mathematicians, and OpenAI established an “advisory group” to judge its math operation.

If you ask students, though, the concessions haven’t changed much for them.

“It is difficult to do research and go to seminars when it feels like none of the individual work will matter much in the future,” one respondent wrote.

• Newport Beach makes me feel like I’m on a luxurious European trip without leaving California.
• There are many ways to enjoy the water, including a dock-and-dine experience or a Duffy tour.
• From outdoor shopping to waterside restaurants, Newport Beach is all about laid-back luxury.

Growing up in the California Bay Area, I’ve been to many beach towns, and they all have their own distinct character.

Santa Cruz is known for laid-back surf culture, but just a few miles down the coast, Carmel-by-the-Sea is all about quiet luxury. There’s a beach town for every taste, and California’s mild weather makes it easy to enjoy the coast any time of year.

But when I’m craving Mediterranean vibes without the pricey flights and jet lag, Newport Beach checks all the boxes.

Newport Harbor feels less like Southern California and more like a European resort town

Newport Beach is home to over 10 miles of pristine coastline, which isn’t uncommon in California, but it’s the harbor, comprised of eight small islands and interconnected waterways, that makes this destination feel like a luxurious European resort town.

The distinct island neighborhoods offer something for everyone, whether that means exploring the sand and surf, riding the historic Ferris wheel at the Balboa Fun Zone, or sipping a cocktail in a poolside cabana.

Our kids love the beach, and on our most recent summer trip, we made that a priority. We swam at the outdoor water park at Newport Dunes Waterfront Resort, where the kids climbed the inflatable slides and cannon-balled into the cool harbor water.

Another day, we grabbed a picnic lunch from A Market on the way to Newport Beach Municipal Beach. We spent the day playing in the sand, running in and out of the water, and watching the surfers catch wave after wave as the tide rolled in.

The food scene centers on the water — and there’s lots of fresh seafood

One of the best things about Newport Beach is the food. Waterfront restaurants are everywhere, giving you plenty of chances to sit back and savor your meals with a view.

We especially loved the Lighthouse Cafe for waterfront views and direct beach access. Our kids enjoyed watching paddleboarders in the harbor while devouring cheeseburgers and lobster rolls, made with fresh-tasting lump lobster meat and drizzled with melted butter.

One of my favorite spots for soaking up Newport Beach’s laid-back luxury vibes is Lido Marina Village, which is perfect for people watching with its ample outdoor dining options.

We also ate dockside at Lido Bottle Works and enjoyed a front-row view of the yacht-filled harbor and glowing pink sunset. It felt like a true escape.

Even restaurants without beachfront views embrace the coastal life.

We enjoyed Mediterranean cuisine at CUCINA enoteca, which featured freshly made pasta and perfectly paired Italian wines. Our kids got to make their own pizza tableside, which was a memorable dinner activity.

At Sushi Roku, my husband and I enjoyed some of the freshest sushi rolls we’ve ever tasted, while my kids were mesmerized by their flaming cotton-candy dessert.

You don’t need a yacht to get a taste of Riviera life

Newport Beach seems made for outdoor living. The Mediterranean climate allows for year-round outdoor experiences, from dining and shopping to boating and surfing.

Many beaches and resorts offer a variety of recreation rentals like kayaks, stand-up paddle boards, and pedal boats, but the best way to enjoy a little bit of the luxury on the water is on Newport’s own Duffy electric boat.

The Duffy was created in Newport Beach decades ago, and it’s still one of the most iconic ways to view the harbor. There are several ways to rent them around town if you want to do just that.

We enjoyed a two-hour self-guided boat ride, and it was the perfect amount of time for our small kids. Even without much boating experience, it was easy to drive through the canals.

Our family enjoyed the scenery and incredible views of waterfront homes and luxury yachts that you can only truly experience from the water.

We even pulled our boat up to Woody’s Wharf for a dock-and-dine lunch that felt like something out of a movie.

Ultimately, I love that Newport Beach offers resort-town amenities without the long-haul flights

Newport Beach has a variety of hotels, from award-winning luxury resorts like The Resort at Pelican Hill to Balboa Bay Resort, which offers direct harbor access.

If you’re looking for glamping vibes, you can check out cottage rentals and RV sites with direct beach access at Newport Dunes Waterfront Resort.

If you want a resort with European-style walkability, consider staying at Lido House. It’s located at Lido Marina Village and surrounded by shops and restaurants, so you have everything you need in one spot.

On our most recent trip, we stayed at VEA Newport Beach, where we enjoyed its family-friendly amenities, spa, and easy access to the shops and restaurants at Fashion Island. Our kids played for hours in the heated pool, and the sunset views were magical.

California is home to some of the most beautiful beaches in the world, and with its mild climate, there’s never a bad time to visit.

However, when it comes to finding Mediterranean vibes stateside, Newport Beach will always be my pick.

• ‘SNL’ fired shots at startup culture in its latest episode.
• Comedian Ben Marshall played Pennywise the clown pitching a new AI company to trap kids.
• In another segment, a Sprite exec admits its new flavor tastes bad because “we used AI to make it.”

“Saturday Night Live” took aim at startup culture and AI across multiple sketches in its Halloween broadcast, including a spoof of the stereotypical big-talking startup dude, channeled through Stephen King’s Pennywise.

“We started a company — it’s called WeAllFloat.ai,” comedian Ben Marshall, playing the malevolent clown, said in the segment. “Instead of trapping one kid with one balloon, what if you had hundreds of AI agents, each with their own digital balloons?”

Before Pennywise came on, “Weekend Update” host Michael Che got a joke in about the floundering stock price of Google’s parent company, Alphabet.

“Today’s Google Doodle hung itself,” Che said, referring to the animations Google sometimes uses on its homepage.

And in another spoof of advertising execs trying to plug a new Sprite flavor on a Latin telenovela, a Sprite rep admits the drink tastes bad because “we used AI to make it.”

“For the first time in history, AI screwed up,” she says sarcastically.

Though “SNL” hasn’t shied away from lampooning AI and the buzzy startup culture associated with it before, Saturday’s broadcast honed in on the Lone Star State as a place where soulless, profit-driven techies are flocking to start new companies.

Indeed, since 2020, more than 200 companies have relocated their headquarters to Texas. Many cite comparatively lax regulatory laws and a business-friendly atmosphere.

Of course, though, moving down south doesn’t guarantee profitability. Pennywise, for instance, might have some trouble getting his AI startup off the ground.

“Got a little crew together of cool, like-minded, sober, predatory tech guys,” Marshall says in the segment. “I live in a loft in Austin with three other motivated young Christians.”