Cole Striler in

Cole Striler

Examiner · DISC type cs
Director of Engineering at WithCoverage
📍 New York City Metropolitan Area, United States

Cole Striler is the Director of Engineering at WithCoverage, an insurtech company he helped build as a Founding Engineer. His background includes software engineering at Apple and a data science internship at NASA after earning his degree from the University of California, Berkeley.

Outside of his main role, Cole is an entrepreneur and an amateur ultra-runner. He has co-founded several ventures, including ClipFM, an AI tool for video editors and podcasters. While at UC Berkeley, he co-founded the Berkeley Jockey Club to create algorithms for horse racing.

He once wrote a book called "X-Play Nation" where he interviewed top executives in the action sports industry about their keys to success.

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Experience
11 Years
Current Role
Director of Engineering
Job Level
Mid-senior
Location
New York City Metropolitan Area, United States
Personality Overview

How Cole shows up

Late Adopter
Overcautious
Status Quo Seeker

They do not like taking risks at all and go for proven options in the end. The only way to convince them is by showing them examples and ample proof. They are thorough and always follow a systematic approach.

Priorities

Topics Cole cares about

Insurtech Disruption
He is passionate about fixing the $300B+ insurance market, aiming to replace outdated methods like emails and PDFs with modern, AI-driven risk management solutions.
Startup Scalability
As a founding engineer who grew into a director, he focuses on scaling teams and technology, sharing his hiring philosophy of offering a "seat on a rocket ship".
+5 more topics Login to view topics
Career

Work history

9-2025
Director of Engineering
WithCoverage
8-2024
Founding Engineer
WithCoverage
7-2020 - 3-2022
Software Engineer
Apple
6-2019 - 8-2019
Data Science Intern
NASA - National Aeronautics and Space Administration
1-2011 - 5-2019
Founder & CEO
Xuxa Socks
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
Bachelor’s Degree
University of California, Berkeley
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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