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Dig Your Heels In

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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 in Male-Dominated Industries Break Through Doubt

Nine profiles of female founders and executives across tech, healthcare, construction, and manufacturing reveal how mentorship, storytelling, and industry visibility overcome imposter syndrome and gender imbalance.

Dig Your Heels In argues that female leaders in traditionally male-dominated fields and high-doubt environments succeed not by ignoring gender dynamics but by directly addressing them through mentorship, visibility, and purposeful career pivots. The channel grounds this thesis in nine named founders and executives who articulate how doubt is real, how to name it, and how concrete professional moves and allies dissolve it.

Drawn from Dig Your Heels In: A Working Women’s Series wi… and 5 more →

“It hadn't occurred to me that I was going to be in the minority in my classes.”

Amy Czuchlewski, Computer Engineering, University of Michigan

By the numbers

1.6%

share of US companies with female CEOs as of 2022

22 years

Allison Grealis' experience in trade association space

6 children

Rachel Neill's experience as parent informing Figgy founding

2012

Year Amber Clore opened A.Clore Interiors

What the channel argues

InsightMegan MacDonald overcame imposter syndrome through mentorship and now leads strategy at Hello Alice, a female-founded company.→
InsightYiDing Yu combined medicine, policy, and technology to become CMO at Olive by solving healthcare systems challenges.→
InsightRachel Neill, veteran parent of six, founded Figgy to address pandemic-driven demand for tech-free child engagement.→
InsightAmy Czuchlewski's early exposure to engineering before recognizing gender disparity left her unencumbered by the gender hurdle.→
InsightJolene Delisle found storytelling as the core lever for branding across brand lifecycles, founding The Working Assembly.→
DataAllison Grealis brings 22 years of trade association experience to lead Women in Manufacturing, addressing male dominance in manufacturing.→

What you'll learn

•Mentorship and solid professional relationships are the concrete counterforce to imposter syndrome in female leadership.
•Women in male-dominated fields succeed by combining adjacent interests and expertise rather than forcing single-track careers.
•Visibility and speaking up in technical and industrial fields directly influence whether other women follow into those sectors.
•Storytelling and brand positioning are recognized levers for female founders across industries from creative services to hardware.
•Career transitions driven by work-life balance and learning opportunities can open entirely new verticals for women.

What to do about it

→Identify and formalize mentorship relationships with experienced female leaders in your industry to counter self-doubt and gain strategic counsel.
→Create visibility programs for women in your sector: speaking engagements, association leadership, and media features shift perception and normalize female presence.
→Build professional networks across adjacent industries and disciplines to unlock non-linear career moves that leverage multiple interests and expertise.

Who and what shows up

Megan MacDonald

Chief Strategy Officer, Hello Alice

Overcame imposter syndrome through mentorship; now leads strategy at female-founded company addressing founder gaps.

YiDing Yu

CMO, Olive; practicing physician, published researcher, serial entrepreneur

Combined medicine, politics, and technology to solve healthcare systems challenges; excited about growth of women in healthcare and tech.

Rachel Neill

Co-founder and CEO, Figgy

Veteran parent of six; identified pandemic need to keep kids active without technology and built solution.

Allison Grealis

President and Founder, Women in Manufacturing Association (WiM)

Brought 22 years of trade association experience to address male dominance in manufacturing through national support and advocacy.

Jolene Delisle

Founder and Head Creative, The Working Assembly

Built branding and creative consultancy on storytelling as core lever for brands across their life cycles.

Questions this channel answers

Q

How do female leaders in male-dominated fields overcome self-doubt?

Through mentorship, sponsorship, and deliberate visibility. Megan MacDonald developed faith in herself through solid mentorship at Hello Alice. Amy Czuchlewski emphasizes the power of getting out there and speaking up in tech.

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

Why are women underrepresented in construction, manufacturing, and tech?

Exposure and visibility gaps, not capability gaps. Women dominate education and healthcare while more men have worked in construction and manufacturing. Jackie Pasierbowicz is helping change the pairing of female and construction.

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

What career paths work for women in tech and healthcare?

Non-linear ones that combine multiple disciplines. YiDing Yu combined medicine, politics, and technology to become CMO at Olive. She noted working in systems best solves healthcare challenges.

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

How do female founders succeed across diverse industries?

By identifying pain points they experienced and building solutions through storytelling and positioning. Jolene Delisle recognized brands need to refine, synthesize, and market themselves using storytelling. Rachel Neill saw pandemic-driven need for tech-free child engagement and founded Figgy.

Dig Your Heels In: A Working Woman’s Series with Rachel … →
Topics:Imposter syndrome and self-doubtFemale founders and C-suite executivesMale-dominated industries: tech, healthcare, construction, manufacturingMentorship and sponsorshipStorytelling and branding
Themes:Imposter syndrome is real but solvable through structured mentorship and communityGender imbalance is an industry visibility and exposure problem, not a capability problemFemale founders and leaders leverage storytelling, systems thinking, and cross-disciplinary expertise as competitive advantages

Industry context

Imposter syndrome affects capable professionals across sectors, while research identifies structural barriers rather than capability gaps as central to gender imbalance in leadership roles.

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