Melia Russell smiles

Docusign’s former CEO took a risk jumping into an older corner of legal tech. The numbers suggest it’s working.

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For years, the software that companies use to draft, sign, and store contracts was legal tech’s center of gravity. Then ChatGPT arrived.

Budgets and attention snapped to agents and copilots, and legal pundits started declaring the contract software category a ticking time bomb.

Ironclad, one of the contract-lifecycle management (CLM) companies that rode the boom, says the obituary is premature.

The company told Business Insider it has crossed $200 million in annual recurring revenue, up from $150 million last May, and its customers include OpenAI, Salesforce, L’Oreal, and Mastercard. Founded in 2014, Ironclad has raised $333 million from investors including Sequoia Capital, Accel, and Bond.

“I mean, not surprisingly, we’re pretty bullish on CLM,” Ironclad CEO Daniel Springer said on a call.

He’s swaggering in a moment when the category is routinely declared dead. Springer bet his career on it. Early last year, he was a free agent, having stepped down as CEO of Docusign in 2022. He said he spoke to 40 companies before taking the Ironclad job in April. Since then, Springer’s been recruiting heavily, pulling in chief technology officer Sunita Verma, who spent 17 years at Google, and longtime Microsoft engineer Herman Man as Ironclad’s new chief product officer.

Springer said he’s heard the “CLM is dead” debate so many times that he compares it to the endless calls for email’s demise. Ironclad’s view is that the need for companies to contract with each other isn’t going away. What is changing, Verma told Business Insider, is how the work gets done: away from rigid workflow software and toward agentic systems that can do chunks of work on their own.

That shift has turned contract lifecycle management into a high-stakes catch-up game. The same platforms that once won clients by organizing contracts now have to show they can automate what legal teams do inside them. In November, Ironclad released a fleet of virtual assistants that it said can handle tasks such as intake, negotiation, and extracting information buried in contracts. Springer said a third of recent new customers also bought its agentic add-on, Jurist.

In that world, Ironclad isn’t just competing with other CLM vendors like Agiloft and Sirion. It’s facing a swarm of startups built on large language models, including Ivo and Spellbook, that promise to handle pieces of contract review. Even the foundational model makers are moving closer to legal workflows. OpenAI has publicly written about building a contract review tool for its own teams. More recently, Anthropic rolled out a legal plug-in that it says can speed up in-house tasks.

Ironclad eyes dealmaking

Springer said Ironclad is open to doing deals this year as it tries to capture more of the market. Some close competitors are for sale, he said, and he’s looked and passed. He added that he isn’t eager to buy another CLM platform, arguing that many older products “aren’t the platforms of the future.”

Instead, he said Ironclad would consider acquisitions that bring a crack team in-house, especially technical talent building something original that might struggle to break into large enterprise accounts on its own. Industry watchers expect more consolidation this year as buyers tire of single-use tools, and more founders start looking for distribution (or a soft landing) inside larger platforms.

Even so, Springer doesn’t think the CLM category is done spawning new entrants. He expects founders will keep building contract software — even if they try to dress it up in new language for the AI era.

“Maybe they won’t call themselves CLM,” he said. “But I will bet you dollars to doughnuts they will call themselves CLM, because that’s what the customer knows.”

Have a tip? Contact this reporter via email at mrussell@businessinsider.com or Signal at @MeliaRussell.01. Use a personal email address and a non-work device; here’s our guide to sharing information securely.




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Why more CEOs and boards are worrying about security: ‘The risk is everywhere.’

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For decades, executive security followed a familiar playbook: Most CEOs traveled freely at home, accepted protection only in high-risk foreign countries, and treated personal safety as a private concern rather than a boardroom imperative.

That world no longer exists.

Mentions of exec security protocols are popping up in more proxy filings, and companies like Starbucks are changing corporate jet policies due to what it calls “significant heightened security concerns.”

These moves follow the December 2024 killing of UnitedHealthcare CEO Brian Thompson in New York City and a shooting at a Park Avenue office building about eight months later.

Both instances shattered long-held assumptions that corporate leaders were at least somewhat insulated from the types of violence more often associated with politicians or celebrities, several security executives told Business Insider.

There isn’t a distinction between low-, medium-, or high-risk anymore, said Dale Buckner, head of the security firm Global Guardian, which works with Fortune 1000 companies.

“The risk is everywhere,” he said.

The news of the disappearance of “Today” co-host Savannah Guthrie’s mother, Nancy, has only added to a sense of unease for high-profile leaders, several of these execs said.

Boards step in

Buckner, a retired US Army colonel who served for more than two decades, said his firm has briefed more boards in the past 11 months than in the previous 14 years combined. Increasingly, Buckner said, boards view CEOs and other C-suite members as assets that must be protected, even if some leaders are leery of perceived constraints on their freedom.

“The board is overruling the CEO who is going, ‘I don’t need this,'” he said.

In regulatory filings, companies have begun to spell out their decisions. Starbucks said last month that, following a security review, it recommended that CEO Brian Niccol use company aircraft for both personal and work travel. While it’s made that recommendation before, the company lifted a spending cap it had in place for personal travel and will instead review those costs each quarter.

Unlike in its previous proxy a year earlier, Starbucks also cited “the existence of credible threat actors.”

Those concerns extend beyond the coffee chain.

Disney requires Bob Iger, who is set to step down as CEO next month, to use company aircraft for both business and personal travel. A security consultant identified “bona-fide, business-related security concerns” for Iger, Disney said in a January filing. That language didn’t appear in the company’s prior filing.

Meatpacking giant Tyson Foods said it hired a consultant during its fiscal year that ended in September to review risks associated with its senior management team “based on the evolving security environment for corporate executives.” One resulting change: requiring certain execs to use company aircraft for both business and personal travel.

Proxy filings by large US public companies that mention “executive security” or “corporate security” rose from 69 in 2023 to 87 in 2025, according to an AlphaSense analysis.

Representatives from Starbucks, Disney, and Tyson Foods didn’t respond to Business Insider’s requests for comment on the nature of the threats executives face.

18 armed agents

While high-profile CEOs have long had protection in high-risk zones, Buckner said what’s grown more common is keeping executives under a 24/7 safety umbrella.

Buckner said that the protocol for one of his protectees, a Fortune 500 CEO, includes 18 armed agents, camera surveillance of the executive’s home, and monitoring of its WiFi network. A former garage on the property now serves as an “op center,” he said.

“I have two to four roving armed agents around their home, 24 hours a day,” Buckner said.

It can be a challenge to determine whether something that starts as disapproval over a company or leader could morph into something more nefarious, security veterans said.

A threat might start out as a joke in poor taste, and a group targeting a company might pick it up. Then, all of a sudden, it becomes a real risk, said Lisa Kaplan, founder and CEO of the risk-intelligence firm Alethea.

‘The reality of risk’

Caleb Gilbert, founder of White Glove Protection Group, a security firm serving large companies and family offices, said the range of people who feel threatened has widened over the past six months.

“The reality of risk is resonating with more people. And that’s different than I’ve seen in the last 30 years,” he said.

One reason is that the cadence of high-profile incidents — from the attempted assassination of President Donald Trump in 2024 to the killing of conservative activist Charlie Kirk in September — hasn’t seemed to slow, Gilbert said. While attacks on business leaders remain rare, many nonetheless feel rattled, he said.

“It used to be where something bad would happen, there’d be time in between, and the executives would forget about it,” Gilbert said. Now, “with the security-minded glasses that they put on, it’s brought everything into focus.”

The cost of protection is part of that view. A small protective detail can cost about $1 million a year, while a full-scale operation can reach $30 million, he said.

In some cases, Gilbert said, even without a board’s prodding, executives are “willing to give up personal liberties that they cherished before for the sake of feeling safe.”

The apparent kidnapping of Nancy Guthrie could lead to demand from executives to detect threats against parents, Kaplan said. Typically, she receives requests from executives to monitor risks to their children.

Buckner said he recently spoke to a group of CEOs in Washington, DC, on security threats. Many reported feeling unnerved, he said.

“It’s palatable,” he said. “They’re scared that they’re in a new world order. They’re not quite sure how to navigate it.”




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A new report found nearly 4 in 10 cancers are linked to preventable causes. Here are the best ways to lower your risk.

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A new report from the World Health Organization found that nearly 7 million cases of cancer worldwide were preventable.

Analyzing 18.7 million new cancer cases in 2022 (the most recent data available to them), researchers found that nearly 4 out of 10 cases were linked to 30 modifiable risk factors, including smoking tobacco, infections like HPV and hepatitis B, and consuming alcohol. Stomach, lung, and cervical cancer accounted for almost half of all preventable cancers in the report.

The findings are a comprehensive assessment of cancer cases globally, which vary greatly by region, so while promising, they come with limitations.

The news comes less than two weeks after it was revealed that colon cancer is now the leading cause of cancer death in people under 50.

Cancer can be caused by a variety of factors, including family history, genetic mutations, and environmental pollutants — all things out of our control — but some risk can be mitigated with lifestyle modifications.

Follow a diverse, Mediterranean-ish diet


Salad

Eating whole, fiber-rich foods can lower cancer risk.

Organic Media/Getty Images



Research shows that diets involving lots of ultra-processed foods (UPFs) are linked to higher cancer risk. They can increase inflammation and disrupt the gut microbiome, increasing the risk of colon and ovarian cancer.

A diet rich in whole foods is the best way to go. Dr. Daniel Landau, an oncologist specializing in genitourinary cancers, previously told Business Insider that he mostly follows the Mediterranean diet, focusing on lean protein, fruits, vegetables, whole grains, nuts, and legumes while limiting red meat (which might be carcinogenic), dairy, alcohol, sugar, and UPFs.

Gut-healthy foods are also important. Dr. Susan Bullman, an associate professor at MD Anderson Cancer Center who specializes in gut health and cancer research, previously told Business Insider that she eats fiber-rich foods like pears and probiotics like kefir to feed beneficial gut microbes. Eating a wide variety of plants, such as swapping out vegetable sides or sprinkling seeds on top of salads, can also improve gut health.

Work out at least 30 minutes a day


Person walking

Even a quick walk counts as exercise, which reduces cancer risk.

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Exercise has long been associated with a reduced risk of cancer. One 2025 trial found that a strict workout regimen for preventing colon cancer resurgence than expensive treatments like chemotherapy. While scientists are still exploring the reasons why exercise is so effective at cancer prevention, they have their theories. Dr. Paul Oberstein, a medical oncologist at NYU Langone, previously told Business Insider that exercise is probably reducing inflammation, which may help slow tumor growth.

Dr. Sue Hwang, an oncologist who was diagnosed with breast cancer, said you should aim for 30 minutes of exercise a day, whether it’s strength training or cardio.

If you can’t make it to a gym every day, she said, even taking a walk or playing with your kids in a playground helps. Even vigorous daily movements, like climbing up stairs or carrying heavy groceries, can cut down cancer risk. Still, the best thing you can do is pencil in real workouts.

Be proactive about screenings


Mammogram

Getting screened can catch cancer earlier.

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Being aware of early cancer symptoms, like blood in your stool for colon cancer, can help you seek screenings earlier than the recommended starting age.

It’s also important to be aware of your family history, any genetic mutations like Lynch syndrome that increase risks of several cancers, or other factors like PCOS for endometrial cancer.

Dr. Thaïs Aliabadi, an OB-GYN who helped Olivia Munn get diagnosed with stage 1 breast cancer, said collecting data on your body, such as previous biopsies or breast density, can help you better assess your risk.




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Taylor Rains

Trump’s threat to ‘decertify’ Canadian planes is a safety risk

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President Donald Trump’s threat to “decertify” Canadian-made aircraft — the backbone of many US carriers’ regional jet fleet — is a threat to aviation safety, industry watchers said Friday.

The president also doesn’t have the authority to unilaterally declare planes unworthy to fly in the US, Henry Harteveldt, an aviation industry authority and president of Atmosphere Research Group, told Business Insider. That authority belongs to the FAA.

The trade spat — another in a continuing back-and-forth between Trump and Canada — comes after Canada hasn’t fully certified newer US-made Gulfstream jets to fly in its skies. (It has certified older models.) Gulfstream planes are used almost exclusively by private aviation companies, governments, and the ultrawealthy.

Trump said on Thursday night, in a Truth Social post, that he would “decertify” Canada-made Bombardier jets until Canada approved the Gulfstream models. He also threatened a 50% tariff on “any and all” Canadian aircraft sold in the US until the situation was corrected.

Bombardier said in a statement that it’s in contact with the Canadian government. The FAA referred Business Insider to the White House. A White House official said decertification would not immediately affect aircraft already in operation; it would apply only to new deliveries.

That would be a relief for US airlines like American, Delta, and United, whose regional affiliates operate Bombardier CRJ aircraft to cities across the country.


SkyWest crj700.

Regional carrier SkyWest, operating on behalf of the Big 3 and Alaska Airlines, is the largest operator of Canadian-made planes. It has 238, per Cirium.

Fabrizio Gandolfo/SOPA Images/LightRocket via Getty Images



Still, any move to decertify these more than 2,000 passenger airliners and private jets — part of almost 5,550 Canadian-made aircraft and helicopters certified in the US, according to Cirium — could trigger thousands of flight cancellations a day. A 50% tariff would likely raise airline ticket prices.

Aviation analysts said Trump’s threat posed a safety risk in itself.

“Anything that intrudes on the turf of safety regulators coming from politics, trade issues, or personal grievances is a very, very bad idea,” Richard Aboulafia, managing director of the aviation consultancy AeroDynamic Advisory, told Business Insider.

Aboulafia said aircraft certification is intentionally non-political for a reason: Regulators are meant to evaluate risk, not respond to trade threats. Once certification becomes a political weapon, trust in the system erodes for manufacturers, operators, and the flying public, he contended.

Why is the Gulfstream certification delayed in Canada?

In Canada’s case, the delay in certification is likely not obstructionism but the result of independent regulatory decisions.

For the Gulfstream G700 and G800, Canada hasn’t completed its own certification, while the FAA has granted Gulfstream a temporary exemption from certain fuel‑icing rules designed to ensure aircraft engines and systems operate safely in extreme cold.

The FAA waiver means Gulfstream has until the end of this year to meet those requirements — meaning the aircraft is operating under essentially conditional certification in the US, despite being allowed to be delivered.

These waivers are not unusual and are typically granted to allow new aircraft to enter service while completing certain technical tests and paperwork, rather than because the planes are unsafe.

Still, history shows what can sometimes go wrong when thorough certification and safety protocols are deprioritized. The most consequential example was the Boeing 737 Max, which suffered two fatal crashes in 2018 and 2019 due to systemic design issues, killing 346 people.

More recently, in early 2024, a door plug separated on another 737 Max due to quality-control issues at Boeing’s Washington factory, further exacerbating scrutiny of production and certification. No one died in that incident.

Part of the reason the 737 Max issues slipped past regulators is that, for decades, global authorities often relied on reciprocal approvals, effectively rubber-stamping each other’s certifications to speed aircraft to market.

The Max disasters exposed the risks of that approach. Today, regulators — including those in Canada — are expected to conduct their own full assessments rather than automatically rely on approvals from foreign authorities.

The FAA itself is taking extra precautions before certifying the Boeing 737 Max 7 and 10, as both aircraft have technical problems that could lead to engine overheating. Boeing initially asked for a waiver but rescinded it amid the scrutiny.




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A Facebook veteran took a big career risk that resulted in a ‘giant failure’ — but embracing a ‘J-curve’ career path paid off

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At 25 years old, Molly Graham was thriving in Facebook’s HR department when a senior executive urged her to transfer out of her stable role and help build a mobile phone instead.

She took the risk — and it could have derailed her career.

But Graham, who later became a C-suite executive at some of America’s biggest companies and philanthropies, now views that risky bet as one of the most important moves she ever made.

“It just felt like falling off a cliff,” Graham, now the founder of Glue Club, said in a recent interview on Lenny Rachitsky’s podcast. “Taking risks, accepting the terrible fall and that experience of falling has been more than worth it.”

Graham described the experience as part of what she calls the “J-curve” — a career trajectory where a risky move leads to an initial drop before eventually producing outsized gains. Visually, she describes it as standing on a ledge, stepping off, sinking briefly, and then rising far higher than where you started — just like the shape of the letter J.

The concept, which she has also written about in her Lessons Substack, challenges the idea of a steady career ladder that steadily moves up and to the right.

Instead of climbing rung by rung with promotions every two to five years, Graham argues that some of the most valuable professional growth comes from jumping into roles you aren’t ready for and surviving any setbacks.

Graham’s own J-curve began when billionaire investor and “All-in” podcast host Chamath Palihapitiya, then Facebook’s vice president of growth, recruited her to help develop a smartphone, encouraging her to make the move by sketching out the J-shaped trajectory on a whiteboard.

He brought her on despite her having no experience in product development, dropping her into rooms filled with engineers and phone specialists with deep subject matter expertise. She recalled feeling like an “idiot” for much of her first six months.


Headshot of Molly Graham, the former Facebook and Google executive, and writer of the Lessons Substack

Molly Graham, the former Facebook and Google executive and writer of the Lessons Substack.

Molly Graham



At her midyear review, Palihapitiya delivered what Graham called the worst performance evaluation she had ever received. But the new experience eventually expanded her expertise.

“Slowly, I remember I had been doing all these trips to Taiwan because we were actually working on hardware and I, at some point, came back from Taiwan and I like drew on a whiteboard for him the layout of a mobile phone, trying to explain to him kind of like why something he wanted to do was not possible,” Graham said. “And I so vividly remember walking out of that meeting being like, ‘Oh like I actually know things.’ And slowly then over the following three years I became an expert in mobile.”

Palihapitiya did not respond to Business Insider’s request for comment.

“The phone itself was a giant failure — a massive, costly failure for Facebook,” Graham told Rachitsky on the podcast. “But it was not a failure for me.”

She credits the experience with teaching her that she could operate far outside her comfort zone — a lesson that later helped her take on senior leadership roles, including serving as COO of Quip, which Salesforce acquired for $750 million, and overseeing operations at the $7.4 billion Chan Zuckerberg Initiative.

The J-curve, Graham said, is especially common at fast-moving companies like Meta, Alphabet, Nvidia, and SpaceX, where leaders value employees who are willing to take big risks early and learn quickly. In those environments, proving adaptability can matter more than checking every qualification box.

Not everyone supported Graham’s decision at the time. She said Facebook COO Sheryl Sandberg, then the number two at the tech giant, advised against the move — as did her father.

“When wiser, more experienced people questioned the job offer, it definitely made me pause,” Graham told Business Insider in a follow-up email. “But my gut felt really strongly that I needed to take the risk.”

That instinct, she said, ultimately helped her discover what kind of work she didn’t want to do, and where her strengths lay. She didn’t want to sift through mock ups of hardware design and argue about a button’s placement. Instead, she sharpened her management skills and prepared to help lead large organizations.

“The much more fun careers are like jumping off cliffs,” Graham told Rachitsky. “They can take you to places that you never could have imagined.”




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