Jill Drader

Pioneer
DISC Type : ids

Business Strategist at Steel Toe Stiletto Ltd.

Greater Calgary Metropolitan Area, Canada

Overview

Jill Drader is a business strategist, author, and speaker with 20 years of experience, specializing in leadership and the construction industry. The founder of Steel Toe Stiletto, she is an award-winning entrepreneur and a University of Calgary Distinguished Alumna recognized as one of Calgarys Top 40 Under 40. People often call her compassionate, focused, positive, and innovative.

Jill is deeply passionate about personal development, offering spiritual direction and nature therapy. She is a harm reduction advocate and co-founder of "Struggle Is Your Success, " a non-profit that teaches youth entrepreneurial skills. Her work often focuses on mental health, wellness, and helping people discover and live their passions through transformation and recovery.

Unique fact: Jill is a journeyman tile setter by trade, which inspired her to found an organization dedicated to attracting and supporting women in skilled trades.

Personality Overview

Friendly But Fast

Driven But Considerate

Decisive But Friendly

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) They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed

Topics They Care About

Women in Trades
Founded Steel Toe Stiletto in 2009 to leverage focus and attention on women in the construction industry and advocate for more entrepreneurial opportunities for them.
Entrepreneurship & Startups
As a founder and business strategist, she provides executive coaching and advises on business start-ups, including in the tech and Web3 sectors.
Youth Mentorship
Co-founded the non-profit "Struggle is Your Success" to teach young people an entrepreneurial mindset and supports programs for youth seeking work-life transformation.

Media Appearances

Jill has no verified media appearances

Work History

1-2009
Business Strategist at Steel Toe Stiletto Ltd.
4-2021 - 8-2023
Chief Strategy Officer at SIYS | Struggle Is Your Success
1-2022 - 7-2023
Strategic Advisor at HighBar Enterprises
9-2021 - 3-2022
Operations at The Accelerator
9-2021 - 12-2021
Recovery Consultant - Harm Reduction Advocate- University of Calgary Recovery Community at University of Calgary

Education

2020 - 2021
Project Management Professional Certificate from University of Calgary
2016 - 2019
Bachelor of Arts from Alberta Bible College

More Information

Social Presence :

Prographics :

Exp : 14 Location : Greater Calgary Metropolitan Area, Canada Job Level : Junior Designation : Business Strategist at Steel Toe Stiletto Ltd.
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Insights For Selling To Jill

During A Call Or A Meeting

DO's

  • During followups, use calls or text if needed, they should be fine
  • Showcase existing customers and use case-studies to grab their attention
  • Build a trustworthy relationship while keeping the product center-stage

DONT's

  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don’t hesitate from asking questions or pushing them, but take a formal approach
  • Don’t be too verbose or overly friendly; a little bit, however, is fine

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jill 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 Jill

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

Insights For Deal Planning

    How fast (or slow) will Jill move?

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

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

You And Jill

Personality Compatibility


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