If You’re Not Failing, You’re Not Learning – Rebecca Grimes

Empathy and compassion are the leadership building blocks Rebecca Grimes has built her foundation on to allow her team to be vulnerable and accept failure as a means to grow and learn.

In this week’s episode Rebecca Grimes, Chief Revenue Officer for Ruby.com breaks down how she accomplished exponential growth as a fairly new leader during such a tumultuous year. Her skills in B2B and B2C marketing has led large scale growth for a number of SaaS companies.

She has been named an Ignite Visibility’s Courageous Marketing Leaders in 2020, 2018 Women to Watch in the DMN Marketing Hall of Femme and one of the top 25 Mobile Women to Watch in 2014 by Mobile Marketer.

Tune in to learn how Rebecca pushed through the uncertainty of leading a company during such a tumultuous year!

Watch or listen to this episode:

Listen on Apple Podcasts


  • “I’m a big believer that you own it, you take accountability, even if it wasn’t you, you fall on the sword, and you learn from it, and you create a path forward.” (24:16-24:25)
  • “When any new leader joins an organization, there is a wealth of knowledge in terms of what’s working, what’s not working, things that we need to be prioritizing.” (13:27-13:35)
  • “I think that is the acceptability of being vulnerable in front, especially now, like with everything that has happened over the last, you know, 14 months since the pandemic started leading with compassion and empathy and, and letting people have space and take a moment is, is something that is probably going to be expected.” (22:22-22:45)
  • “And we’ve worked very hard to create an environment where that is acceptable and expected that you are failing all the time.” (24:53-25:00)


Rebecca Grimes: LinkedIn
Ruby: LinkedIn
Ruby: Website

Empellor CRM Website
[email protected]
Empellor CRM LinkedIn