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Kent Bennett

Partner
Cambridge

Roadmaps

Biography

Kent Bennett is a partner in Bessemer’s Cambridge office focusing on B2B application software and consumer “earthquakes.”

Before his career in venture capital, Kent was a creative executive for an entertainment production company, where he developed and sold original material including a network television pilot and a feature film. He began his career with Bain & Co., where he worked on projects in industries spanning IT, retail, consumer products, healthcare, and biotech.

Kent earned an MBA from Harvard Business School, where he was a Baker Scholar, and graduated summa cum laude in systems engineering from the University of Virginia, where he was a Jefferson Scholar.

Portfolio Highlights

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Getting to know Kent

 

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Toast CEO, Co-founder & Director, Aman Narang, President, Co-founder & Director, Steve Fredette and Kent

Betting on the impossible

Kent first encountered the Toast team after Endeca founder Steve Papa, advised him to invest in three of his best people who were leaving Endeca to start a new venture. Although Kent wasn’t ready to invest, he offered the Toast founders an empty office next to his. They grew close as Kent watched the Toast team tackle the seemingly impossible task of building a restaurant point of sale (POS) system in a crowded market. Despite Kent’s initial conviction that Toast was doomed to fail, he was impressed by the founders’ unwavering determination and began to see that some elements of Toast’s technology were radically differentiated from the competition. Realizing their potential, Kent led Toast’s first institutional round in 2015. Over the years, Kent has watched Toast grow exponentially and assemble one of the strongest teams he has ever seen. To this day, he feels lucky to have been invited along for the ride. Read the full story.

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GlossGenius Co-Founders: CEO, Danielle Cohen-Shohet and Chief Business Officer, Leah Cohen-Shohet

Product obsessed

The most successful founders Kent has met share a dogged focus, deep understanding of the industry they operate in, and complete product obsession. Even as the business gets bigger and more complicated, these founders never lose sight of their true North Star: the product itself.

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A guiding approach

Kent takes a rational, straightforward, and steady approach working with founders. He doesn’t come with a predefined set of answers on how to run their business and enters each conversation with an open mind. His goal is to share relevant information and his own perspective to help founders make informed decisions and navigate the challenges of company-building.

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The power of radical honesty

Kent holds an unwavering belief in honesty at all times. He once read a book called “Lying” by Sam Harris, which strongly advocates for never lying, even in easy situations. This message clicked for him, and he began to express himself directly and honestly, even when it was difficult or uncomfortable. Through this experience, he realized that people are often nervous about being honest with each other, but when they are, they can connect on a deeper level and have much more meaningful conversations.

Finding (musical) harmony

When Kent sits down at the piano or picks up his guitar, time seems to disappear. He loves playing songs by ear and composing his own tunes. With three young children, he may not have hours to lose himself to music anymore, but when he does find time, playing the piano or guitar never fails to get him into a flow state and find happiness.

Portfolio Companies

Indicates Enduring

Provi

Enterprise
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Provi

Provi is a communication platform and open marketplace that simplifies the operations for bars, restaurants, and retailers in the beverage industry.

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Investors

Kent Bennett

Founded

2014

Partnered

2019

Roadmaps

Enterprise

Recurrency

AI & ML Enterprise
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Recurrency

Recurrency is the developer of an ERP automation platform for planning tools in the distribution ecosystem and offers enterprise resource planning with automated sales, purchasing, and pricing workflows in the tool, and on-demand recommendations, enabling wholesale distributors and B2B retailers to automate and optimize their pricing and sales processes.

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Investors

Kent Bennett

Founded

2018

Partnered

2021

Roadmaps

AI & ML Enterprise

News

Our investment in Recurrency: A $7 trillion dollar market hiding in plain sight

Toast

NYSE: TOST
Vertical Software Enterprise Fintech
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Toast

Toast is an all-in-one point-of-sale and restaurant management platform for businesses in the food service and hospitality space. In September 2021, Toast went public (NYSE: TOST).

NYSE: TOST
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Investors

Kent Bennett

Founded

2011

Partnered

2015

Roadmaps

Enterprise Fintech Vertical Software

Articles

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Scaling to $100 Million
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Six product strategies to catalyze your Second Act
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From Memo to IPO: Toast takes on the US restaurant industry
 0's 1's and lines overlapping
Ten lessons from a decade of vertical software investing
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State of the Cloud 2022
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Forecasting 101

Investment Memo

Read the Toast memo

Insights & News

In the News