Jacob May-Smith

Critic
DISC Type : C

Manager of Legal Operations at Bitsight

Boston, Massachusetts, United States

Overview

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.

Personality Overview

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.

Topics They Care 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.
Large-Scale Change
A key listed skill is "Large Scale Change Management, " indicating a focus on implementing significant operational shifts within large corporate environments.

Media Appearances

Jacob has no verified media appearances

Work History

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

Education

Advanced Paralegal Professional Studies from Boston University
Bachelor of Business Administration - BBA from University of Alabama at Birmingham

More Information

Social Presence :

Prographics :

Exp : 16 Location : Boston, Massachusetts, United States Job Level : Middle Designation : Manager of Legal Operations at Bitsight
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Insights For Selling To Jacob

During A Call Or A Meeting

DO's

  • Leverage facts and figures wherever possible; use percentages, numbers etc.
  • Use phrases like ‘expect X% improvement’, ‘data clearly shows’ etc.
  • Keep some extra margin while sharing pricing, they are likely to negotiate later

DONT's

  • Make extra effort to not seem pushy or confrontational
  • Avoid phrases like ‘trust me’, ‘others just love’ etc.
  • Don’t try too hard to build a relationship with them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jacob is

  • Proof of ROI, low pricing and objective proof points are the important factors for them.
  • Will you ever get a clear answer from Jacob

  • They do not mind saying no if they believe that it is the right decision.

Insights For Deal Planning

    How fast (or slow) will Jacob move?

  • Their decision-making is neither very fast nor very slow, they are somewhere in between.
  • Can Jacob take some risk or not?

  • They can take risks if their analysis shows that it would be worth it.

You And Jacob

Personality Compatibility


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