Jessica Gutierrez spent a decade building the systems that are supposed to support people at work. Enablement at SAP, training programs for 5,000 partners at JOEY, learning strategy at Vancity, and a seat on the leadership team at The Learning Network. She is a certified Mental Health First Aider, a Prosci Change Management Practitioner, and has over 100 hours of facilitation, mentoring, and coaching behind her.

In April 2026 her son Nathan was born and died. She went back to work, and found out what those systems look like from the other side.

Today she is the founder of Calm-hearted, a pregnancy and infant loss platform offering writing, practical support, remembrance, and workplace guidance. It has three front doors: one for grieving parents, one for the family and friends around them, and one for the employers trying to get it right.

In this episode we get into the leadership decisions she got wrong, the difference between being liked and being trusted, what she learned about what people actually need from the person leading them, her six kinds of workplace readiness, and the one nobody talks about.

Takeaways:

• Jessica Gutierrez has spent her career building learning and enablement programs at SAP, JOEY, Vancity, and The Learning Network.
• Being liked and being trusted are different things, and the gap between them shows up long before a crisis does.
• Culture is not created by a crisis. It is revealed by one, and what gets built on ordinary days determines what holds.
• Bereavement readiness does not require managers to become grief experts. It requires them to have decided certain things in advance.
• Repair readiness, knowing what to do after your organization has already handled something badly, is the piece most workplaces never consider.
• A grieving employee should not become the project manager of their workplace’s response.
• Returning to work is an administrative milestone, not a recovery one, and treating the two as the same is where good intentions most often fail.

Chapters:

1:26 Early Career

10:37 Personal Experiences

17:22 Experiences in HR Systems

28:25 Repair Readiness

37:42 Calm-Hearted

45:51 Closing Remarks

🔗 Links mentioned in this episode:

Calm-hearted, support for parents, family and friends, and workplaces: https://www.calmhearted.ca/

Calm-hearted at work: https://www.calmhearted.ca/workplaces

Jess on LinkedIn: https://www.linkedin.com/in/jessicagutierrez-calmhearted/

Workplace resources and notes on this episode, coming soon: https://www.calmhearted.ca/post/eh-list

Please note: this episode discusses pregnancy and infant loss. Calm-hearted offers lived-experience and educational support, not crisis care, medical advice, or counselling. For immediate help, call or text 988, dial 211 for community resources, or call 911 in an emergency.

🎙️ The Eh List brings you founders, CEOs, and leaders from across Canada sharing the real stories behind how they got there.

Our discussion today centres on mentorship, storytelling, and what it actually means to lead. I had the distinct privilege of conversing with Sam Thiara, Adjunct Professor at SFU's Beedie School of Business and founder of Ignite the Dream Coaching and Consulting, whose career began with 86 rejection letters and a job as a hospital janitor before spanning ICBC, the Vancouver Olympic Bid, and 22 years at Simon Fraser University.

Throughout our dialogue, we examined why leadership is determined not by title or position but by whether others choose to follow, and why Sam draws a firm distinction between transactional networking and genuine relationship building. We further explored the frameworks he has developed over roughly 5,500 one-on-one conversations, including his CARE model, the practice of intentional pausing, and the anchor points that guide his decisions.

Sam's insights offer a grounded counterpoint to conventional career advice, reminding us that the journey itself, rather than the destination, is where the meaningful work occurs.

Takeaways:

• Sam Thiara has mentored thousands of students and professionals over 26 years with the Greater Vancouver Board of Trade's Leaders of Tomorrow program.
• Leadership is a lifestyle rather than a position, and it is the people around you who determine whether you have earned the title.
• Being overlooked early in his career shaped a lasting commitment to giving anyone, from high school students to CEOs, his time and attention.
• Understanding who you are must precede deciding what you want to do, as the latter tends to materialize once the former is clear.
• Intentional pausing and non-negotiable anchor points provide direction when opportunities and setbacks arrive unexpectedly.
• Organizations frequently falter by treating people as secondary to process, overlooking the strengths individuals naturally bring.
• A single blank puzzle piece, given to more than 5,000 people worldwide, serves as a reminder that no one is meant to navigate the journey alone.

Links mentioned in this episode:

Sam's coaching: https://www.sam-thiara.com/coaching/

Greater Vancouver Board of Trade: https://www.boardoftrade.com/

Sam on LinkedIn: https://www.linkedin.com/in/sthiara/

Our discussion today centres on the profound transformations occurring within the realm of product management, propelled by advancements in artificial intelligence. I had the distinct privilege of conversing with Brian Yan Muk, a product manager at Apply Digital, whose extensive experience encompasses leadership roles at renowned organizations such as AT&T, PGE, Moderna, and the NFL.

Throughout our dialogue, we delved into the intricacies of leadership in both small and large organizational contexts, emphasizing the importance of empathy in decision-making processes. Furthermore, we explored the implications of AI on product development and the evolving expectations of leadership in today's digital landscape.

Brian's insights not only illuminate the path forward for aspiring leaders but also underscore the necessity of adaptability and continuous learning in an ever-changing environment.

Note: The views shared in this episode are Brian's own and don't represent the views of Apply Digital.

Takeaways:

• Brian Yan Muk has led product teams in prestigious organizations, demonstrating significant leadership skills.
• The essence of effective leadership lies in empathy and understanding team dynamics and individual contributions.
• AI is reshaping business processes by automating tasks, thus requiring leaders to adapt their methods accordingly.
• Successful product development hinges on clear communication and stakeholder involvement throughout the process.
• Effective leadership necessitates decisiveness, even if it involves making unpopular decisions for the greater good.
• Continuous curiosity and experimentation are crucial for adapting to the rapidly changing technological landscape.

Links referenced in this episode:

• www.applydigital.com
• www.sfu.ca
• www.enactus.org
• www.linkedin.com/in/brianyanmuk