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.
