Jackelyn Keller, a marketing leader, strategist, and educator—and Founder of Jackwell Partners, a marketing consultancy—shares her journey from sales assistant to CMO and what it taught her about trusting your instincts.

Known for translating complex technology into clear, actionable strategy, she explores career pivots, building confidence without certainty, and why mentorship and relationships often matter more than resumes.

Takeaways

Confidence isn’t about having all the answers–it’s trusting that you’ll figure it out.
Career growth comes from trying new things rather than staying where you’re comfortable.
Relationships often matter more than what’s on your resume.
Mentorship works best when it’s rooted in empathy and active listening.
Taking care of yourself shapes how you show up at work and in life.

Chapters

00:00 Introduction to Jackelyn Keller and her background

02:30 Building a career across marketing, teaching, and entrepreneurship

06:10 Knowing when to push through versus when to pivot

07:45 Taking risks before feeling ready

10:00 Redefining confidence as self-trust

11:40 Overcoming fear of public speaking through teaching

14:15 Mentors who shaped her career

16:20 What makes a great mentor

17:20 Why leaders struggle to ask for help

18:20 Managing self-doubt and personal pressure

20:00 The importance of outside perspectives

22:20 Advice for early-career professionals

23:15 The value of mentorship and community

OhHello Ep. 119 On Confidence, Career Pivots & Choosing Movement Over Comfort