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Business conversations for professionals who build on their own terms.

Dig Your Heels In is a business podcast for professionals who resist shortcuts and build careers and companies on their own terms. Episodes cover leadership, entrepreneurship, and the decisions that define long-term professional success. The channel speaks directly to B2B practitioners who value substance over speed.

9 episodes

Channel Brief·Dig Your Heels In · 9 episodes

Updated Jun 26, 2022

Women leaders overcome doubt to reshape male-dominated industries

Nine interviews with female founders, executives, and innovators show how mentorship, early exposure, and storytelling help women advance in tech, healthcare, construction, manufacturing, and design.

Dig Your Heels In argues that female leadership thrives when women receive solid mentorship, early exposure to their field, and platforms to speak up. The channel proves this through direct testimony from nine women across industries—from C-suite roles at Hello Alice and Lenovo to founders in branding, construction, and interior design—each tracing her breakthrough moment to a mentor, a family example, or deliberate visibility work.

Drawn from Dig Your Heels In: A Working Women’s Series wi… and 3 more →

“Advertising was really the place where storytellers go.”
Jolene Delisle, Founder and Head Creative, The Working Assembly

By the numbers

1.6%

share of U.S. companies with female CEOs in 2022

22 years

Allison Grealis' experience in trade association space

6 children

Rachel Neill's family size, informing pandemic product inspiration

What the channel argues

InsightMegan MacDonald reached C-Suite at Hello Alice through solid mentorship that developed her faith in herself.→

InsightYiDing Yu combined medicine, politics, and technology by solving healthcare system challenges rather than practicing alone.→

InsightAmy Czuchlewski studied Computer Engineering at University of Michigan without initially realizing women were in the minority.→

InsightAndi Huels worked across oil and gas, industrial automation, and AI before becoming Head of AI at Lenovo North America.→

DataAllison Grealis draws on 22 years in trade associations to lead the Women in Manufacturing Association.→

What you'll learn

•How imposter syndrome affects female leaders and mentorship addresses it by building confidence and faith in accomplishments.

•Why early exposure to a field (like a parent working in tech) can blind women to gender hurdles they might otherwise internalize.

•How women founders use storytelling and branding expertise to help other female entrepreneurs refine and market themselves.

•Why cross-industry career moves give women touchpoints on smart tools and systems thinking that prepare them for leadership roles.

•How female leaders in male-dominated sectors like construction and manufacturing are deliberately changing gender dynamics by promoting involvement.

What to do about it

→Establish mentorship programs that pair emerging female leaders with executives who have navigated imposter syndrome and built confidence.

→Create early-exposure initiatives in schools and families to normalize women in tech, construction, manufacturing, and engineering before gender bias becomes internalized.

→Build platforms and speaking opportunities for female founders and leaders to share their stories and expertise, making visibility and voice a core retention strategy.

Who and what shows up

Megan MacDonald

Chief Strategy Officer, Hello Alice

Illustrates how mentorship overcomes imposter syndrome and enables women to reach C-Suite at a female-led company.

YiDing Yu

CMO, Olive; practicing physician and serial entrepreneur

Demonstrates how combining medicine, politics, and tech helps women solve systemic healthcare challenges rather than staying siloed.

Rachel Neill

Co-founder and CEO, Figgy

Identifies a pandemic-driven market need for tech-free engagement tools by observing parent pain points.

Andi Huels

Head of AI, North America, Lenovo

Built AI expertise through deliberate cross-industry moves in oil and gas, automation, and supply chain before reaching top tech role.

Allison Grealis

President and Founder, Women in Manufacturing Association

Leverages 22 years in trade associations to address gender imbalance in manufacturing sector through a national organization.

Questions this channel answers

How do women overcome imposter syndrome in leadership?

Through solid mentorship that builds faith in their education, experience, and accomplishments, as exemplified by Megan MacDonald's path to Chief Strategy Officer.

Dig Your Heels In: A Working Women’s Series with Megan M… →

Why do women in male-dominated fields struggle to see themselves as leaders?

Early exposure to the field (like a parent working in tech) can blind women to gender hurdles, making them unaware they are in the minority until adulthood.

Dig Your Heels In: A Working Woman’s Series with Amy Czu… →

How do female founders build successful businesses?

By using storytelling and branding expertise to help clients and other founders refine, synthesize, and market themselves throughout their business life cycles.

Dig Your Heels In: A Working Woman’s Series with Jolene … →

What career paths prepare women for AI and innovation leadership?

Cross-industry experience across automation, supply chain, logistics, and systems thinking gives women the touchpoints on smart tools needed for executive roles in emerging tech.

Dig Your Heels In: A Working Woman’s Series with Lenovo’… →

How can industries like construction and manufacturing attract more women?

By discussing current gender dynamics, promoting female involvement, and highlighting career transitions that offer better work-life balance and cross-functional learning.

Dig Your Heels In: A Working Woman’s Series with Jackie … →

Best place to start

Dig Your Heels In: A Working Women’s Series with Megan MacDonaldIntroduces the channel's core thesis: mentorship builds confidence and enables women to reach C-Suite despite imposter syndrome.

Dig Your Heels In: A Working Woman’s Series with Amy CzuchlewskiShows how early exposure to a field blinds women to gender hurdles and why visibility matters across industries.

Topics:Imposter syndrome and self-doubt in female leadersMentorship and early career exposureWomen in tech, healthcare, construction, and manufacturingStorytelling and brand-building for foundersWork-life balance and industry switching

Themes:Mentorship as the antidote to imposter syndromeEarly exposure blinds women to gender hurdlesStorytelling and voice drive female founder success