Jacob May-Smith in

Jacob May-Smith

Critic · DISC type C
Manager of Legal Operations at Bitsight
📍 Boston, Massachusetts, United States

Jacob May-Smith is a strategic leader in corporate legal operations, currently serving as a Manager at Bitsight. With a background that includes managing a $1. 5 billion annual legal spend at Liberty Mutual and holding a Project Management Professional (PMP) certification, he specializes in leveraging technology and driving large-scale change management.

His career path shows a unique transition from retail operations, where he was the Head of Retail Operations at Banana Republic, to the complex world of corporate legal services. This diverse experience equips him with a distinct perspective on operational strategy and business planning in different environments.

He successfully combines his skills in legal technology and operational strategy, having designed workflows and integrated new technologies in his roles.

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Experience
16 Years
Current Role
Manager of Legal Operations
Job Level
Middle
Location
Boston, Massachusetts, United States
Personality Overview

How Jacob shows up

Information Seeker
ROI Driven
Critic

They prefer to analyze logically and value objective facts over emotions. It is very likely that they will negotiate pricing or other important terms. Unless the value is proven by data, they are unlikely to value fancy features.

Priorities

Topics Jacob cares about

Legal Operations
His entire recent career focuses on innovating legal operations, managing large budgets, and improving workflows at companies like Bitsight and Liberty Mutual.
Technology Integration
He has a stated skill in Technology Integration and experience in leveraging existing tech while co-developing new solutions in the legal space.
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Career

Work history

11-2024
Manager of Legal Operations
Bitsight
1-2021 - 5-2024
Operations Manager - Legal Strategic Services
Liberty Mutual Insurance
1-2018 - 1-2020
Senior Legal Administrative
Liberty Mutual Insurance
1-2017 - 1-2018
Legal Administrative
Liberty Mutual Insurance
1-2011 - 1-2017
Head of Retail Operations
Banana Republic
In the press

Media appearances

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Education
Advanced Paralegal Professional Studies
Boston University
Bachelor of Business Administration - BBA
University of Alabama at Birmingham
Social presence
in
Behavioral profile

DISC profile (public)

C

Calculativeness (C)

Calculativeness (C) reflects the degree to which a person is likely to be cautious, systematic and analytical. Those scoring high tend to emphasise quality and accuracy.

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