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Ep. 105 How to lead with confidence and vulnerability

This guest was promoted to a leadership role in mobile marketing just before the pandemic hit. Not having all the answers was an unfamiliar feeling that felt like failure at the time. She reflects on what she’s learned about being a leader, thanks in part to working with an executive coach, and shares hacks and habits for success.

Erin Webster-Shaller is the Vice President of Marketing at the Boston-based weight loss company, Lose It. She has a degree in biomedical marketing and is interested in the intersections of health, wellness, and business.

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Questions Erin Answers In This Episode

  • What was the transition like from director to VP?
  • How did you become comfortable with not having all the answers and being a little vulnerable?
  • What is it that you’re doing every day for yourself so you can be the person and leader you need to be? What are some of those non-negotiables for you?
  • Tell us about your career journey.
  • What’s the worst advice you’ve received in your career?
  • How do we encourage women to feel more confident in speaking up?
  • What do you go to for inspiration?


  • 1:14 About Lose it and Erin
  • 4:25 Stepping into the VP role during Covid
  • 7:38 Not having the answers
  • 9:15 Perspective from peers
  • 12:00 Working with an executive coach
  • 14:00 Non-negotiable self-care habits
  • 18:11 Erin’s career journey
  • 26:45 The worst advice Erin’s gotten
  • 29:02 Hacks for speaking up
  • 32:30 Sources of inspiration


(8:27-8:45) “Getting really inquisitive. Trying to be more of a coach and not a manager, and create space for the team to do their job. I realized over the last year, that’s what I should have been focused on instead of trying to understand everything that I needed to know as part of this job.”

(11:03-11:20) “That notion of confidence and uncertainty, I think of it as, ‘I’m confident that we’ll find the answers. I’m confident that we’ll be able to solve this problem. I don’t know how we’re going to get there, but I believe in the team or I believe in my ability or whoever to get us to the place that we need to go.’”

(13:02-13:25) “The whole mindset of this coaching program is that people will become better leaders when they’re more in tune with themselves, essentially. When you know who you are as your person, your authentic self with a capital ‘S,’ you’re more likely to show up in a way that’s authentic to you and to be a leader that people can believe in and follow and they want to work for.”