Laura Bennett put a price on risk. Then she took one.

Laura Bennett had spent years calculating risk before she acquired a rather personal example of it: a company with a name, a business plan and no policies sold. Embrace Pet Insurance began in 2003. Its first policy followed in September 2006. The interval deserves a little respect. Three years is a long time to be explaining what your business will eventually do.

The business had already won a prize. At Wharton, Bennett and her teammates took first place in the business plan competition with a pet insurance concept. That supplied encouragement, useful introductions and a credible line in a pitch. It left the founders with an extensive list of things that still had to happen.

Bennett would spend 14 years as Embrace’s CEO. Later came digital consumer insurance at Chubb, consulting and, by October 2026, plans for another pet insurance venture. Across those chapters, there is a recurring occupation beneath the job titles: she likes making a business work. The arithmetic matters. So do the people expected to live with it.

The competition was the easy part

Embrace grew out of a student project, but Bennett was hardly a beginner in insurance. She had worked for 12 years before pursuing her MBA, including actuarial work in Toronto and Dublin. Business school offered a chance to consider a different direction. She arrived with an existing profession and the curiosity to see where else it might take her.

The Wharton team included Alex Krooglik, who became her Embrace co-founder. After the competition, the original four-person team divided into two pairs. Bennett and Krooglik went on to build in Cleveland. A classroom exercise had become an undertaking with its own address, obligations and need for money.

There is a neatness to the dates when they are placed in a company history. In practice, each date marks something the founders had to persuade somebody else to do. JumpStart selected Embrace for funding in September 2004. The first policy arrived two years later. Success in a competition had opened a door; the business still needed a succession of people willing to walk through it.

An actuary learns to sell

Bennett’s professional credentials helped when Embrace approached underwriters at Lloyd’s of London. An actuary, Wharton MBAs and a business plan competition victory gave a prospective partner reasons to take the founders seriously. In a business built around accepting other people’s risks, reassurance has commercial value.

Fundraising required a different education. Competition judges could offer feedback. Investors who declined often supplied little that the founders could use. Bennett had a tart description of that social courtesy: “No one tells you that you have an ugly baby.” A polite rejection can be exquisitely mannered and almost entirely uninformative.

She learned to present the business to audiences with different incentives. Investors were assessing a possible return. Underwriters needed confidence in an unfamiliar operation. The same idea had to survive both conversations. Technical fluency helped, but someone still had to stand up, explain the proposition and invite questions.

That wider range of work became part of her account of entrepreneurship. A founder could have a specialty and still find herself responsible for tasks far outside it. The job description expanded whenever the company needed something done. An MBA could prepare her to see possibilities; running Embrace required her to act on them.

The blog before the policy

One of Bennett’s tools was writing. At Wharton, she kept an online account of her student experience, beginning in 2001. She remembered readers introducing themselves at the Thursday pub gatherings. An online audience had become people she could meet across a room.

She carried that habit into Embrace, beginning an industry blog in April 2005, before the company was selling policies. There was something usefully exposed about that choice. A prospective customer could encounter the thinking behind the business while the business itself was still being assembled.

For a company selling an unfamiliar product, explanations were part of the work. Bennett’s account of the blog emphasizes transparency and conversation. It gave Embrace a public voice before it had much of a trading history. She was already doing the patient work of answering questions that a future sales operation would need people to ask.

Her professional presentation in 2014 listed LinkedIn, Twitter and Facebook. The online conversation had become an established part of how she showed up for the business. Long before every executive was advised to have a personal brand, Bennett had found practical uses for being reachable in public.

Forty-seven people, and counting

By early 2014, growth had acquired a particularly tangible form: more colleagues. Embrace had hired 17 people during the previous year, taking its staff from 30 to 47. The additions were concentrated in customer service, claims and technology. A growing company needed people who could answer the phone and people who could keep its systems working.

New backing also brought a change in the investor group. Beauvest US bought out the venture investors, whose investment timetable had run its course. Bennett welcomed an investor with insurance experience and an appetite to support further growth. A business can be progressing while an investor is ready to leave; their clocks do not always agree.

An office move was on the agenda, too. These are the less photogenic rewards of expansion: recruiting, finding space, making operations more efficient. The idea that once occupied a business plan now required desks. More customers meant more work, and the work had to land somewhere.

Outside Embrace, Bennett also helped build connections among entrepreneurs. She founded the Burning River Coffee Community for women in Northeast Ohio and chaired the industry association NAPHIA. Her name appeared on Insurance Business America’s Elite Women list in 2016. The work was extending beyond one company’s immediate needs.

A breakfast meeting with room for a child

Her approach to mentoring has a pleasingly practical detail. When a woman founder asked about bringing a child to a meeting, Bennett understood the question from experience. She had raised daughters while building Embrace. She publicly welcomed the arrangement rather than treating it as an awkward exception.

In one account, she described meeting entrepreneur Charisma Curry over breakfast with Curry’s two-year-old on her lap. Bennett shared stories from her own years combining children and company building. Advice can begin with a spreadsheet. Sometimes it begins by making the person across the table feel able to stay there.

This is consistent with the version of balance she offered in a 2012 interview. Priorities had to be chosen. Help had to be found. Perfection had to be allowed to depart, preferably before it rearranged the entire household. Her answer gave no impression that successful people possess a secret additional day in the week.

There were personal keepsakes and pleasures beyond the business. Growing up in a Royal Navy family meant frequent moves in England. Her grandmother’s watch remained a symbol of independence. She enjoyed jigsaw puzzles, food and travel away from the customary routes. Pie could qualify as breakfast. An actuary is entitled to exercise discretion.

She also returned to Wharton for a 2013 reunion panel on women aspiring to leadership, alongside Alissa Finerman and Helen Wong. The former business plan contestant was now part of a conversation about helping others advance. Her route back to campus had supplied something a classroom alone could scarcely offer: years of decisions for which she had been responsible.

A builder inside the big company

After Embrace, Bennett took time for consulting before joining Chubb in 2019. She wanted to build again, while also considering the steadier circumstances she needed for her family. A role inside a large insurer offered a way to pursue both. The choice gave her another setting in which to test her instincts.

Blink, Chubb’s digital consumer brand, addressed customers who wanted insurance to be easier to understand and buy. Its development involved listening to millennial consumers who felt existing offerings missed their needs. For Bennett, the work included the experience surrounding a product as well as the product itself.

By 2022, her responsibilities had expanded to president of the North American Digital Consumer Division. In a 2023 video conversation, she explained the appeal of offering insurance alongside a purchase, such as a travel ticket. Timing could make the offer relevant. Customers were already doing something; insurance needed to fit that moment.

She also wrote about gathering with colleagues in Jersey City: leadership conversations, customer experience discussions and breakfast with service team members visiting from Texas and Tennessee. Digital business still involved people getting together. Her enthusiasm for those meetings suggests that the human part of operations remained an attraction in its own right.

The next business, with evidence

By October 2026, Bennett was discussing another beginning: Falls Forward Holdings, a new pet insurance venture following her Chubb and Gosling’s Leap consulting chapters. At Cleveland’s BIG Summit, she spoke about investigating an idea, working through its possibilities and finding the people who could help make it happen.

“Go with your gut, but with evidence.”

Laura Bennett · October 2026

The sentence suits a career that has included both models and leaps. It allows an instinct to start the conversation and requires it to tolerate questions. Bennett’s route offers plenty of examples of what comes afterward: backing, partners, colleagues, customers and decisions that will not fit neatly inside a competition entry.

She has already spent years turning one pet insurance idea into an operating company. Now she is taking another into the world. The actuary gets to ask the questions again. The founder gets to discover which answers will hold.