David Pearson

Commander
DISC Type : D

Director of Engineering at January

New York, New York, United States

Overview

David is a Director of Engineering at January with over 15 years of experience scaling teams and infrastructure. He has overseen product suites generating over $2. 4B in annual GPV. He is an AWS Certified Cloud Practitioner and is often described by colleagues as innovative, motivating, and enthusiastic.

Outside of his primary role, David is passionate about mentorship and works as a part-time engineering coach, guiding other engineers and managers in their careers. His professional interests include major technology companies like Electronic Arts (EA).

He once co-chaired the engineering manager hiring process at Square, where he defined and improved the entire recruitment pipeline.

Personality Overview

Impact-Driven

Strong-Willed

Decisive

More than the product, they care about the impact of the product.  They prefer to be the ones controlling the conversation or defining the terms. They like to move fast and expect the same from others.

Topics They Care About

Scaling Engineering Teams
Has extensive experience growing and managing engineering organizations ranging from 10 to 110 people and has led hiring initiatives for key leadership roles at Square.
AI in FinTech
Leads engineering for January's AI-native collections platform, using data intelligence to create better outcomes for consumers and creditors.
Site Reliability
Has recently been actively seeking consulting expertise in site reliability engineering, showing a focus on AWS infrastructure, Datadog, and modern deployment techniques.

Media Appearances

David has no verified media appearances

Work History

3-2025
Director of Engineering at January
4-2024 - 3-2025
Director of Engineering, Web E-commerce, Staff & Customers at Square
9-2023 - 4-2024
Director of Engineering, E-commerce at Square
2-2022 - 3-2025
Engineering Coach (Part-time) at MentorCruise
6-2018 - 10-2023
Director of Engineering, Square Online, Platform & Operations at Square

Education

2006 - 2009
Bachelor's degree from Cégep de Chicoutimi

More Information

Social Presence :

Prographics :

Exp : 10 Location : New York, New York, United States Job Level : Mid-senior Designation : Director of Engineering at January
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Insights For Selling To David

During A Call Or A Meeting

DO's

  • Speak about competitive differentiation that your product offers
  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Get to the point quickly instead of spending time doing small talk

DONT's

  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Don’t take too much time in sending them information if they ask for any
  • Avoid being a storyteller and don’t try to oversell

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with David is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from David

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will David move?

  • They can reach decisions fairly quickly if they are convinced.
  • Can David take some risk or not?

  • They don’t mind risks but can be quite binary about them.

You And David

Personality Compatibility


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