I’m Jill Drader and I’m the founder of Steel Toe Stiletto, and a professional leadership and construction educator with over 15 years of experience in post-secondary facilitation, entrepreneurship, and consulting to the non-profit and the construction industry. I have helped more than 200 entrepreneurs build start-up businesses and grow their ideas for the past 15+ years.
As a journeyman by trade, I formed Steel Toe Stiletto in 2009, when I found a need to leverage focus and attention to women in the trades. My organization solved the problem of attracting more women into the trades with the project, Women in Work Boots, an online community dedicated to women’s networking in skilled trades and construction and advocating for more women to explore entrepreneurial opportunities in the trades industry.
In 2014, I was awarded the Top 40 Under 40 designation as a result of advocacy work for women in the trades and recovery. During this time, I developed the Entrepreneurial Trades program for Junior Achievement in conjunction with the Calgary Board of Education and have continued advocacy work through public speaking and engagement events.
In 2015, I was granted the Honourable Albertan award through the Alberta Legislature as a result of my advocacy work. In 2016 and over the next four years, I focused on building a retreat series, Roots Leadership and Spiritual Wellness, which trained over 200 people on connecting their stories to the forests in the Rocky Mountains. In recent years, I’ve been approached by organizations to consult and facilitate projects in non-profit, post-secondary institutes and private corporations.
I was sought out by Fresh Start Recovery Centre in 2017 for my leadership and management skills. While working for the organization, I focused on outreach and was responsible for assisting the Director of Operations with construction of sober living facilities. Currently, I serve of the Substance Use Advisory Committee at the University of Calgary.
Over the past ten years, I’ve spoken at over 50 events on entrepreneurship, careers in trades, women in work, recovery resiliency, and mentorship. I’ve been a keynote speaker at the University of Calgary, NAIT, SAIT, Big Brother and Big Sisters, United Way and federally for the Ministry of Status of Women. I grew up in Ontario and moved to Calgary in 1997. Since 1999, I’ve traveled to more than 20 countries. I speak English and French.
I’ve demonstrated success in entrepreneurship and leadership through creating award winning projects and taking them to market. I’m an adaptive thinker and innovator.
Top 40 Under 40 Award Article, 2014
"Working with Jill has been an incredible experience. She is a very genuine person with a ton of relatable knowledge. She has many ideas and suggestions about aspects of my business I had not considered. Working with her has lit a fire within me to achieve my dreams. She presented me with a detailed and easy to understand summary of our first meeting, which was beyond my expectations and greatly appreciated. I am grateful for the opportunity to work with her and would highly recommend her to anyone." -
"Jill is an incredible business coach! Through my years of business ownership I have learned so much from having such a great mentor. With the years of experience in business and her natural ability as a great leader, she makes it easy and exciting to learn from. With her leadership and advice, I have walked through legal, financial, and growth pains successfully. Jill is a great listener and always has sound guidance for me."
Public Speaking + Facilitation
emPOWER, SAIT Women in Construction event, February 2019, Calgary
Women's Faith Retreat, October 2018, Victoria BC
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, November 9-11, 2018, Field BC
United Way, Keynote and Workshop for Big Brothers Big Sisters, August 22, 2018, Calgary
The Ace Class, Keynote Speaker, May 12, 2018, Babes Who Brunch series, Calgary
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, June 1-3, 2018, Field BC
ROOTS Leadership and Spiritual Wellness Retreat, May 2018, Field BC
Scholar’s Academy, Workshop, March 23, 2018, University of Calgary
Power Up Lunch and Learn, March 22, 2018, DATACM Calgary
University of Calgary, Keynote on mental health and addiction, January 29, 2018
ROOTS Leadership and Spiritual Wellness Retreat, November 13-15, 2017, Private Retreat
The Ace Class, Keynote Speaker, November 2017, Babes Who Brunch series, Calgary
The Ace Class, panel speaker, October 12, 2017, Dream Girl film discussion on women and work
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, October 13-15, 2017, Private Corporate Team Building
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, October 20-22, 2017, retreat: Spiritual Harvest
Attached, June 2017, topic: the stigma of addictions, Big Secret Theater
People Are Pearls, May 2017, topic: resiliency and trauma, Kensington Gallery
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, June 9-11, 2017, retreat: grief and trauma
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, May 2017, retreat: The Big Lie
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, March 2017, retreat: Spiritual Gardening
She Recovers NYC conference, March 2017, topic: women in recovery, The Conrad Hotel
Scholar’s Academy, workshop: overcoming fear, January 2017, University of Calgary
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, September 23-25 2016, retreat: Brave Hearts
Celebrated Alumni Ceremony, May 2016, topic: resiliency, University of Calgary
Question Period, May 2016, Alberta Legislative Building, topic: women and work
ROOTS Leadership and Spiritual Wellness Retreat 3-day retreat, May 13-15 2016, retreat: Plan to Recover, BC
Transformation Weekend 3-day retreat, March 11-13, workshop: goal setting, Toronto
Leadership Panel, January 2016, topic: leadership, University of Calgary
SAIT School of Business, January 2016, workshop: Build Your Business, Calgary
SAIT School of Business, November 2015, topic: business of trades, Calgary
University of Alberta, June 5, 2015, Graduate Student's Association Keynote Speech, Edmonton
Women in Trades Toronto, June 2015, topic: trades business workshop, Toronto
Pine Lake Women’s Retreat, June 2015, topic: faith and recovery,
Alberta Women Entrepreneur’s Forum, March 2015, topic: women and work, Ottawa
Women in Trades, October 2014, workshop: building a trades business, Kamloops
SAIT School of Construction, April 2014, topic: leadership, Calgary
Status of Women Federal, March 24, topic: Women in Work Boots project, Ottawa
NAIT Women in Trades and Technology (WITT), March 2014, topic: trades, Edmonton
Women and Leadership Panel, October 2013, Calgary Construction Assn. Committee
Trade Up! Women’s Conference, June 2013, Okanagan College, Kelowna
GETT (Girls in Trades and Technology), May 2013, topic: women in trades, Edmonton
Green Careers, March 2013, topic: green careers, Calgary
World of Choice, Junior Achievement, March 2013, topic: non-traditional work, Calgary
World of Choice, Junior Achievement, May 2012, topic: female Journeyman, Calgary
Publications, Contributions and Seats
Boards and Committees
University of Calgary, Committee on Substance Use and Student Mental Health, 2015-Present
Calgary Construction Association, Women's Committee, 2014-2016. Facilitated BuildEx Panel
Academic Non-Fiction Contributions
Construction Connect, September 2017, Interview in magazine pages 8-10
Calgary Arts Development, September 2016, Interview online
Level Best - Supporting the Advancement of Women in Construction, National Project Advisory Committee Member, 2014 – 2017
Women Work & the Web – How the Web Creates Entrepreneurial Opportunities. Edited by Carol Smallwood. December 2014. My projects are featured in two chapters; Women and Work Boots, and Digital Entrepreneurship.
Women in Work Boots Digital Magazine, A digital magazine I created as a PDF download on my Women in Work Boots website. The magazine was downloaded thousands of times by students across Canada in high school trades courses as an inspiration and activity guide.
Bill C-243, www.billc-243.ca. A maternity leave strategy and amendment to the Employment Insurance Act. I was a participant based on the relevance to my own experience with layoff due to pregnancy
Introduction into Alberta Legislature May 2016
Shaw TV Interview 2016