Michael Prestileo in

Michael Prestileo

Observer · DISC type ci
Chief Strategy Officer at Guardian Life
📍 Boston, Massachusetts, United States

Professional overview including current role context, leadership scope, domain focus, and career trajectory to help you understand background relevance before outreach.

Key behavioral and communication insights including interaction style, decision-making tendencies, and motivation drivers to tailor messaging and personalize conversations.

Business priorities, areas of interest, and practical outreach recommendations that can improve conversion quality for this professional.

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Experience
13 Years
Current Role
Chief Strategy Officer
Job Level
Leadership
Location
Boston, Massachusetts, United States
Personality Overview

How Michael shows up

Example Seeker
Assertive
Curious

They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They often ask many questions and rely heavily on information and documentation. They are generally good communicators and can be hard to convince.

Priorities

Topics Michael cares about

Strategic Priorities
Topic insights and context to help personalize outreach and discovery conversations.
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Career

Work history

5-2025
Chief Strategy Officer
Guardian Life
3-2022 - 5-2025
Chief Commercial Officer, Group Benefits
Guardian Life
11-2020 - 3-2022
Head of Group Benefits Strategy, Product, & Underwriting
Guardian Life
12-2019 - 11-2020
SVP; Product, Pricing, & Underwriting
Lincoln Financial Group
5-2018 - 12-2019
SVP; Operations
Lincoln Financial Group
In the press

Media appearances

Media appearances and press coverage highlighting public visibility and thought leadership.
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Education
2008 - 2010
Master of Business Administration (MBA)
Boston University
2002 - 2006
Bachelor of Science (BS)
Worcester Polytechnic Institute
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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