Cole Striler

Examiner
DISC Type : cs

Director of Engineering at WithCoverage

New York City Metropolitan Area, United States

Overview

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.

Personality Overview

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.

Topics They Care 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He is passionate about fixing the $300B+ insurance market, aiming to replace outdated methods like emails and PDFs with modern, AI-driven risk management solutions.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".
AI for Creators
He co-founded ClipFM, a tool that uses AI to save podcasters and video editors hours of time by automatically creating shareable clips from long-form content.

Media Appearances

Cole has no verified media appearances

Work History

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

Education

Bachelor’s Degree from University of California, Berkeley

More Information

Social Presence :

Prographics :

Exp : 11 Location : New York City Metropolitan Area, United States Job Level : Mid-senior Designation : Director of Engineering at WithCoverage
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Insights For Selling To Cole

During A Call Or A Meeting

DO's

  • Be firm in your communication and stay in control
  • Expect them to be vague in response to your questions, ask firmly and pointedly
  • Expect them to be slow and cautious, encourage them to ask more questions

DONT's

  • Don't rely on relationship building even if they act pleasantly
  • Don't use phrases like 'do not worry', 'i promise' etc.
  • Don't push them too hard to make fast decisions, give them time

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Cole is

  • Adoption by others is very important to them, followed by confidence in ROI.
  • Will you ever get a clear answer from Cole

  • They don’t say no often, they push out the decisions or keep going around in circles.

Insights For Deal Planning

    How fast (or slow) will Cole move?

  • They don't like to hasten, so their speed of decision-making may be slow.
  • Can Cole take some risk or not?

  • They have little willingness to take risks, and prefer making calculated decisions.

You And Cole

Personality Compatibility


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