Pat Cullen

Enigma
DISC Type : dci

Founding CTO at YearOne (Techstars 2020)

North Port-Sarasota Area, United States

Overview

Pat Cullen is the Founding CTO at YearOne, an AI-powered software engineering intelligence platform. He has extensive experience scaling technology startups, notably growing the engineering team at Carrot Fertility from 3 to over 70. Peers describe him as a transparent, strategic, smart, and empathetic leader who excels at connecting engineering with broader business goals.

Outside of his primary CTO role, Pat co-founded Guava Tri, an AI-powered triathlon coaching platform, indicating a strong personal interest in endurance sports like swimming, biking, and running. He is a hands-on technologist who actively explores and shares insights on the latest AI coding assistants like Claude Code and Cursor.

Interesting fact: Pat secured strategic investment from Accenture Ventures for his current company, YearOne, in July 2025.

Personality Overview

Challenger

Fast Follower

Hard To Convince

They can sound friendly and charming but can quickly change gears to become inquisitive and probing  They are likely to ask many questions and look heavily for supporting proof as well as information. They are generally strong communicators and are not easy to convince.

Topics They Care About

AI in Software Engineering
As CTO of YearOne, he is building an "AI copilot for engineering team dynamics" and frequently posts tips about using AI coding tools like Claude Code and Cursor.
Scaling Engineering Teams
He successfully scaled the engineering, security, and data functions at Carrot Fertility, growing the team from 3 to over 70 employees during a period of rapid expansion.
Triathlon Training
He co-founded Guava Tri, a platform that develops AI algorithms to create personalized training plans for triathlon athletes, suggesting a deep personal passion for the sport.

Media Appearances

Pat has no verified media appearances

Work History

5-2024
Founding CTO at YearOne (Techstars 2020)
4-2024
Co-Founder at Guava Tri
3-2024 - 7-2025
Advisor at Talent Llama
9-2022 - 3-2024
Senior Vice President of Engineering at Carrot Fertility
4-2019 - 9-2022
VP Engineering at Carrot Fertility

Education

2008 - 2009
Master from The College of Saint Rose
2004 - 2008
B.S from The College of Saint Rose

More Information

Social Presence :

Prographics :

Exp : 11 Location : North Port-Sarasota Area, United States Job Level : Leadership Designation : Founding CTO at YearOne (Techstars 2020)
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Insights For Selling To Pat

During A Call Or A Meeting

DO's

  • Leverage 'negging', or the art of asking negative questions like "you must not be convinced yet..."
  • Build rapport slwly without rushing, it will come handy to handle hard questions later
  • Let them lead the discussion, create opportunities for them to speak if they are not very forthcoming

DONT's

  • Avoid long presentations and just 'high-level' value proposition, dive into the details
  • Don’t brush off any concerns, take all questions seriously. They are easily deterred
  • Don’t rely excessively on your relationship with them to win the deal even if you come to form one

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Pat is

  • Proven value, strong objective evidence are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Pat

  • They are practical and friendly, but can give a clear response with a little prodding

Insights For Deal Planning

    How fast (or slow) will Pat move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Pat take some risk or not?

  • They evaluate their decisions systematically and do not take risks that often, unless you can get them to develop strong conviction

You And Pat

Personality Compatibility


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