Kyle Jessey

Enigma
DISC Type : dci

Senior Director of Finance at HqO

Greater Boston, United States

Overview

Kyle Jessey is a strategic finance leader with over a decade of experience scaling VC and PE-backed SaaS and fintech companies. Currently the Senior Director of Finance at HqO, he specializes in FP&A, RevOps, and M&A. He holds degrees from the Isenberg School of Management, UMass Amherst, and The University of Manchester.

A unique aspect of his career is his experience as a fractional CFO for diverse businesses, including a $100M e-commerce company and providing M&A advisory for a $100M paper and packaging firm.

Personality Overview

Persuasive & Assertive

Fast Follower

Friendly Yet Blunt

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

Topics They Care About

SaaS Growth
Specializes in scaling VC and PE-backed SaaS businesses, having overseen a 3x ARR expansion in a previous role at Level Data.
M&A Execution
Directly responsible for executing five M&A transactions at a middle-market SaaS company and has performed M&A advisory work.
Proptech Ventures
Previously served as the Head of Finance for two distinct Proptech ventures, one in the short-term rental space and another at the intersection of healthcare and real estate.

Media Appearances

Kyle has no verified media appearances

Work History

2-2026
Senior Director of Finance at HqO
1-2025 - 1-2026
Fractional CFO at Self-employed
9-2023 - 7-2025
Director of FP&A at Level Data
4-2022 - 5-2023
Head of Finance at Summer
5-2020 - 4-2022
Head of Finance at HealthQuarters

Education

2011 - 2015
Bachelor’s Degree from Isenberg School of Management, UMass Amherst
2013 - 2014
Bachelor of Business Administration (BBA) from The University of Manchester

More Information

Social Presence :

Prographics :

Exp : 9 Location : Greater Boston, United States Job Level : Senior Designation : Senior Director of Finance at HqO
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Insights For Selling To Kyle

During A Call Or A Meeting

DO's

  • Use a combination of data as well as stories for your pitch, a ppt might not be necessary
  • Use phrases like ‘clear evidence’, ‘data-based results’ etc.
  • Help them realize that any personal risk in making this decision is far less compared to what the results could mean for them

DONT's

  • Avoid making offhand commitments, understand the root of their concerns first
  • Don’t rely excessively on your relationship with them to win the deal even if you come to form one
  • Don’t be too objective but make sure to pad your storytelling with data points

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Kyle is

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

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

Insights For Deal Planning

    How fast (or slow) will Kyle move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Kyle 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 Kyle

Personality Compatibility


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