Jenny Dempsey: Flipping Your Career Through Storytelling and Curiosity

Welcome to Escalations, a series where I’ll be sharing stories of some amazing careers that started in Customer Support. While many of these will be compiled into a book, I will also be regularly sharing stories here, too. If you like this content, please consider subscribing or sharing. 

Introduction: The Starting Point

Jenny Dempsey's customer experience journey began unexpectedly during her college days. Initially, she took a part-time tech support role simply to fund her surfing adventures and social life. However, she quickly discovered a passion for frontline support.

Jenny's natural affinity for connecting with people helped her transition swiftly from frontline roles into supervisory and managerial positions, laying the groundwork for her future career pivots.

The Growth Path

Jenny's career evolved significantly through her roles at various tech startups, eventually culminating in a leadership position. Her pivotal moment came in 2012 when she co-founded the "Customer Service Life" blog with her former boss, Jeremy Watkin. This venture introduced her to a broader CX community, significantly expanding her professional network and opening doors to speaking engagements and thought leadership opportunities.

Despite facing a challenging layoff in 2022, Jenny seized the moment to explore freelance community engagement and, notably, began a furniture restoration side business. This creative pivot not only provided financial support but reinforced her passion for rejuvenating customer experiences—even for neglected furniture.

Implementing This in Your Own Career:

• Identify transferable skills early.

• Leverage creative outlets as career enhancers.

• Build community proactively.

Breaking Through: Lessons & Key Decisions

1. Find and Repurpose Your Golden Threads

Jenny emphasizes the importance of recognizing and repurposing existing skills rather than starting from scratch. She shares how her customer experience background provided her with foundational skills such as asking insightful questions and structuring effective processes, which she successfully applied in a completely new domain: furniture restoration. By acknowledging and repurposing these skills, Jenny found herself confidently navigating unfamiliar territory.

How You Can Apply It:

• Identify core competencies from your current role.

• Experiment with applying those skills in new contexts.

2. Storytelling Sets You Apart

Throughout her career, Jenny has effectively used storytelling to communicate data compellingly, making her indispensable. She highlights a recent example where she turned a complex data set into a relatable story about an apartment complex facing significant challenges. Her creative presentation not only resonated deeply with the company's VP but also immediately established her as an essential voice within the organization, quickly earning her a spot in critical company discussions and strategic meetings.

How You Can Apply It:

• Translate complex data into relatable narratives.

• Regularly practice your storytelling skills.

3. Curiosity Drives Career Growth

Jenny believes curiosity is a primary driver for career advancement and has observed its impact firsthand among colleagues and mentees. She notes that team members who consistently exhibited curiosity by asking thoughtful questions were the ones who frequently moved into leadership roles. Jenny also applied this mindset in her own career by continually seeking out new knowledge, engaging with different ideas, and asking deeper questions about processes and outcomes.

How You Can Apply It:

• Continuously question processes and seek improvements.

• Engage proactively with new concepts and ideas.

4. Burnout as a Catalyst for Change

Jenny highlights that burnout, while challenging, can serve as a powerful indicator to reevaluate and pivot your career. She openly shares how experiencing burnout became a crucial turning point for her, forcing her to reassess career choices and priorities deeply. This moment of vulnerability ultimately propelled her toward a more balanced and fulfilling professional trajectory.

How You Can Apply It:

• Listen actively to signs of burnout.

• Use burnout experiences to reassess career priorities.

5. Relationships are Your Superpower

Jenny attributes her continued professional success and resilience largely to the strong relationships she cultivated over the years. The relationships she nurtured within the CX community provided essential support during difficult career transitions and opened doors to new opportunities. Jenny emphasizes that genuine human connections remain valuable, regardless of career fluctuations.

How You Can Apply It:

• Prioritize genuine connections within and beyond your company.

• Regularly nurture your professional network.

Actionable Takeaways

• Curiosity is career fuel.

  • Regularly question and explore to continuously expand your professional scope.

• Storytelling elevates your value.

  • Transform mundane data into impactful narratives to boost visibility.

• Relationships sustain careers.

  • Actively invest in building authentic, enduring professional relationships.

• Burnout signals necessary growth.

  • Recognize and act on burnout early to proactively shape your career.

• Skills are universally transferable.

  • Recognize and reuse your core abilities across different roles and industries.

Where They Are Now & Final Words of Advice

Today, Jenny balances her role as a Reputation and Marketing Specialist with her passion projects, including furniture restoration and hosting "The Career Flipper Podcast." She remains committed to community-building and authentic storytelling.