Cale Helmer

Trailblazer
DISC Type : DI

Lead Technical Sales Enablement Partner at Snyk

Ottawa, Ontario, Canada

Overview

Cale is a Lead Technical Sales Enablement Partner at Snyk with over two decades of experience helping companies enhance their training initiatives. He specializes in developing educational strategies and building skills from individual contributors to the C-Suite. Colleagues often describe him as an empathetic, creative, and amazing mentor with a natural ability to teach.

Outside of his professional life, Cale recently took a three-week trip to Scotland with his wife. They explored the country extensively, driving over a thousand miles from coast to coast, visiting castles, touring distilleries, and enjoying the scenic highlands. He is also an alumnus of the University of Toronto.

Unique fact: During his trip to Scotland, Cale and his wife made new wedding bands together.

Personality Overview

Charismatic

Achievement-Oriented

Values Relationships

They are charming and can persuade others to support their decisions.  They will bat for you if they come to believe in you. They are more likely to accept new and exciting technologies.

Topics They Care About

Learning and Development
His entire career, including roles at Snyk, Payscale, and Shopify, has focused on building educational strategies and growing core skillsets within organizations.
Sales Enablement
Currently a Lead Technical Sales Enablement Partner, he focuses on equipping sales teams with the knowledge and tools they need for success.
AI in Enablement
He holds recent certifications in "AI For Everyone" and "Prompt Engineering for Project Managers, " showing an interest in applying AI to his field.

Media Appearances

Cale has no verified media appearances

Work History

11-2025
Lead Technical Sales Enablement Partner at Snyk
6-2024 - 10-2025
Program Manager II Education at Payscale
6-2023 - 6-2024
Program Manager II, Partners at Payscale
4-2022 - 5-2023
Manager, Technology Enablement at Shopify
8-2018 - 5-2021
Manager, Corporate Learning and Development at Assent Compliance Inc

Education

1997 - 2001
B.A. from University of Toronto - Innis College
Finance from Corporate Finance Institute® (CFI)

More Information

Social Presence :

Prographics :

Exp : 13 Location : Ottawa, Ontario, Canada Job Level : Mid-senior Designation : Lead Technical Sales Enablement Partner at Snyk
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Insights For Selling To Cale

During A Call Or A Meeting

DO's

  • Talk about yourself and some of your achievements at the start of the conversation
  • Build a trustworthy relationship while keeping the product center-stage
  • Display high self-confidence and expect them to have a strong personality.

DONT's

  • Avoid unnecessary negativity or slowness
  • Don’t force involvement of other stakeholders unless it is critical
  • Don’t hesitate from asking questions or pushing them, but take a friendly approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Cale is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Cale

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Cale move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Cale take some risk or not?

  • If necessary, they will be ready to take risks.

You And Cale

Personality Compatibility


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