Paul Cowan

Pioneer
DISC Type : DIS

Chief Growth Officer at When I Work

Greater Toronto Area, Canada

Overview

Paul is a growth-focused marketing executive specializing in scaling B2B SaaS companies through customer-centric strategies and product-led growth. He holds a BA from Western University and is consistently described by colleagues as a smart, energetic, and professional leader who excels at communication.

Outside of his professional life, Paul is an avid outdoorsman who enjoys building things at his cabin and skiing. He stays current on emerging technology, showing a deep interest in the evolution of AI and its broad impact on marketing and the internet economy.

Unique fact: He co-founded Feast, Inc. , a food-tech startup that delivered chef-made meals to urban customers.

Personality Overview

Dynamic But Sincere

Decisive But Friendly

Driven But Considerate

They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed  If they are convinced, they can become very strong champions for your product They have the unique ability to win both love and respect from their team (or outsiders)

Topics They Care About

AI in Marketing
His recent social media activity centers on how AI agents, LLMs, and new commerce protocols are reshaping the internet economy and creating new challenges for marketers.
B2B SaaS Growth
His entire career, from Shutterstock to FreshBooks and When I Work, has focused on delivering scalable and profitable growth in high-velocity B2B SaaS environments.
Product-Led Growth
He has hands-on experience driving PLG initiatives, including building product roadmaps to expand into new segments and enhance the customer journey.

Media Appearances

Paul has no verified media appearances

Work History

9-2023 - 1-2025
Chief Growth Officer at When I Work
9-2019 - 4-2023
Chief Marketing Officer at FreshBooks
9-2017 - 9-2019
VP, Enterprise and SMB Marketing at Shutterstock
5-2015
Growth Advisor and fCMO at CINC Revenue Growth and fCMO Services
5-2015 - 7-2017
CMO, Co-Founder at Feast, Inc

Education

1992 - 1996
BA from Western University

More Information

Social Presence :

Prographics :

Exp : 9 Location : Greater Toronto Area, Canada Job Level : N/A Designation : Chief Growth Officer at When I Work
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Insights For Selling To Paul

During A Call Or A Meeting

DO's

  • Ask them for a lunch or coffee once some rapport has been established
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • Mostly stick to your standard pitch and qualifying script, but add some stories or anecdotes to it

DONT's

  • Don’t be very informal during the early interactions even if they are being so themselves
  • Don't lean very heavily into providing too much information, sharing whitepapers etc.
  • Avoid focusing only on the product or its ROI, keep building trust subtly

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Paul is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Paul

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Paul move?

  • They are generally fast movers and can take quick decisions
  • Can Paul take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Paul

Personality Compatibility


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