Kyle Jessey in

Kyle Jessey

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Senior Director of Finance at HqO
📍 Greater Boston, United States

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.

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Experience
9 Years
Current Role
Senior Director of Finance
Job Level
Senior
Location
Greater Boston, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

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Priorities

Topics Kyle cares 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.
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Career

Work history

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

Media appearances

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

DISC profile (public)

DISC behavioral profile

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