Jesse Greenberg in

Jesse Greenberg

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Head of Strategic Accounts at Laivly
📍 Winnipeg, Manitoba, Canada

Jesse Greenberg is the Head of Strategic Accounts at Laivly, specializing in enterprise technology sales, AI-driven customer experience, and go-to-market strategy. A graduate of the University of Manitoba, he was a founding AE at Laivly, playing a key role in building the sales strategy that led to its spin-out as an independent company.

Outside of work, Jesse is an accomplished Ultimate Frisbee athlete, having founded the club at his university and competed for Team Canada. Described by peers as charismatic and thoughtful, he has also participated in startup events, co-developing and pitching new business ideas over intensive weekends.

Unique fact: He was named Valedictorian and won the Kleyson Award for high academic standing in Logistics and Supply Chain Management.

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Experience
9 Years
Current Role
Head of Strategic Accounts
Job Level
Mid-senior
Location
Winnipeg, Manitoba, Canada
Personality Overview

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Decision Approach
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Priorities

Topics Jesse cares about

AI in Customer Experience
His role at Laivly and focus on agent assist, workflow automation, and voice AI show his expertise in using technology to enhance customer care.
Go-to-Market Strategy
He acted as a "GTM Builder" in a prior role, creating sales processes, pricing, and collateral from the ground up to successfully launch a new division.
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Career

Work history

6-2026
Head of Strategic Accounts
Laivly
2-2025 - 6-2026
Director - Contact Center/CX/AI Consulting
Simplify
9-2024 - 2-2025
Director Client Strategy
Laivly
7-2021 - 11-2024
Sr. Account Executive
Laivly
11-2019 - 7-2021
Sr. Account Executive
IntouchCX
In the press

Media appearances

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Education
Bachelor’s Degree (Honours)
University of Manitoba
Bachelor of Commerce (B.Com.)
KEDGE Business School
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

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