Jill Drader in

Jill Drader

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Business Strategist at Steel Toe Stiletto Ltd.
📍 Greater Calgary Metropolitan Area, Canada

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.

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Experience
14 Years
Current Role
Business Strategist
Job Level
Junior
Location
Greater Calgary Metropolitan Area, Canada
Personality Overview

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Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Jill cares 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.
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Career

Work history

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

Media appearances

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Education
2020 - 2021
Project Management Professional Certificate
University of Calgary
2016 - 2019
Bachelor of Arts
Alberta Bible College
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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