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GREGORY FLYNN

Innovative and Entrepreneurial Executive

Delivering high-value strategic projects and high ROI have been key outcomes of a successful career as an innovative, entrepreneurial leader. Known for developing effective solutions to challenges and generating a lasting impact on business growth and success. Passionate about pushing boundaries with technology and product development to maximize startup growth and success.

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Expertise in transformative deals, startups, corporate innovation, and venture capital. Exceptional record leading teams through strategy development, piloting emerging technologies, due diligence, negotiation, and startup investments. Recognized with multiple company and industry awards for accomplishments on critical deals.

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Currently located in Canton, MA.

Open to travel, remote, hybrid & on-site.

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EXPERIENCE

EXPERIENCE

August 2019 | June 2023

Program Director

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Oversaw day-to-day operations while recruiting and managing the Partner Network comprised of leading insurers and real estate owners, including Travelers, The Hartford, Hartford Steam Boiler, AXA XL, UBS Real Estate, and Silverstein.

September 2016 | November 2018

President

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Founded this technology startup to bring junior golfers and college golf coaches together to achieve success. Developed the company vision, designed and created the product, and built a solid team.

August 2007 | June 2016

Vice President of Corporate Development

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Strategically guided investment initiatives for early-stage companies and startups in healthcare, insurance, and fintech.

Results

RESULTS

8X

Coordinated investments in 36 startups over four years, leading to 8X return on capital invested.

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$2M

Designed and orchestrated 50+ pilots of emerging technologies across Internet of Things, artificial intelligence, geospatial, mobile and electrification/net zero leading to $2M of revenue and deals for the startups.

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$20B+

Led complex, multi-functional, multi-country project teams through the deal process to execute $20B+ in merger and acquisition deals.

Expertise

EXPERTISE

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  • Venture Capital

  • Corporate Innovation

  • Startup Growth

  • Emerging Technologies

  • Pilots

  • Term Sheets

  • Deal Sourcing

  • Due Diligence

  • Valuation

  • Negotiation

  • Capital Raising

  • Financial Analysis

  • Product Development

  • Business Strategy

EDUCATION

EDUCATION

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Bachelor of Business Administration (BBA) 
Investment Finance 

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Meet Cynthia
Q & A

Q & A

Why did you choose your profession?

I have been fascinated by investing for as long as I can remember. When I was young, I devoured books on great investors like Warren Buffett, Ben Graham, George Soros, and Peter Lynch. I also have a very creative side and love working alongside startup founders and entrepreneurs.

Who is the one person who has done the most, to shape you into who you are today? How was the person significant to you?

My father has been a consistent source of support and inspiration to me over the years. He took an active role in helping me develop my potential when I was young and emphasized the value of education in reaching goals.  

What has been the greatest accomplishment of your life so far? Is there anything you wish to do even better?

I take a lot of pride in knowing that I added a great deal of value in my career. This includes transforming sports recruiting in golf, helping NBC acquire and integrate Universal, and helping build a new venture capital firm from the ground up.

How would your peers and team members describe your responsiveness as a leader?

Overall, I try to be someone people enjoy working with and life is too short to do it any other way. I am always working to strike the balance between firm and fair. Teams should strive to accomplish big goals, but people also need to feel valued and appreciated to do their best work.

Interests & Hobbies

INTERESTS & HOBBIES

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GOLF

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AVID READER

Grand Piano

JAZZ PIANO

CONTACT

TESTIMONIALS

“I worked with Gregory through the Upward Labs program. Gregory was an excellent mentor. He supported us in the search for product market fit, implementing and monitoring pilots in partnership with Fortune 500 companies, and preparing pitches for investors. His knowledge of the tech sector combined with his experience investing in startups makes him the ideal mentor. Thank you Greg”

Theo Niktabe, Founder – Mavitoo 

"Greg is an exceptional talent in the corporate development space. His ability to thoroughly dive into complex markets like healthcare, BPO and insurance and spot the winning value propositions is one of his unique talents. We worked together for 7 years in Genpact M&A where the landscaping proactive market research he constructed led to several proactive winning space acquisitions for the business. He is a solid executor, commercially savvy, team player, and skilled at identifying the right companies to match/execute a strategy.

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​And he is also highly skilled with the golf clubs!”

PJ Kaputa, SVP and Global Head of Corporate Development – EXL

Testimonials
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