David Pearson in

David Pearson

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Director of Engineering at January
📍 New York, New York, United States

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.

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

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Decision Approach
Work Preference

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Priorities

Topics David cares 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.
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Career

Work history

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

Media appearances

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Education
2006 - 2009
Bachelor's degree
Cégep de Chicoutimi
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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