Jesse Speakman in

Jesse Speakman

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Manager, Technical Services and Business Intelligence at Fourteen IP
📍 Orlando, Florida, United States

Jesse is an IT leader in Orlando with over 20 years of experience building and managing technical teams in the hospitality industry for brands like Four Seasons and Disney. He is a Certified Scrum Master, described by colleagues as "expedient and precise, " who excels at creating unified and productive work environments.

He is a vocal advocate for responsible technology implementation, frequently sharing his thoughts on data security, the practical limits of AI, and the societal importance of digital privacy. He believes in fostering a positive and fun work environment, leading his teams by example to improve morale and efficiency.

He has a strong conviction that "without private transactions freedom cannot exist, " highlighting his deep concern for personal privacy in an increasingly digital world.

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Experience
13 Years
Current Role
Manager, Technical Services and Business Intelligence
Job Level
Middle
Location
Orlando, Florida, United States
Personality Overview

How Jesse shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Jesse cares about

IT Team Leadership
Passionate about building positive, collaborative, and productive team environments, with experience leading teams of over 20 members.
Data Security
Expresses concern about development practices that lead to data breaches and believes in making systems secure and less accessible to inexperienced developers.
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Career

Work history

1-2023
Manager, Technical Services and Business Intelligence
Fourteen IP
12-2021 - 10-2022
Director of IT
Four Seasons Hotels and Resorts
11-2018 - 9-2021
IT Manager, Systems Management Services
Wyndham Destinations
6-2016 - 11-2018
Complex IT Manager
Walt Disney World Swan and Dolphin
3-2012 - 6-2016
Implementation Manager / Project Coordinator / Team Lead / Support Analyst
Wyndham Worldwide
In the press

Media appearances

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Education
2010 - 2011
Diploma
Herzing University
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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