Sonder and Sales with Jordan Benjamin

Most of us underestimate the extent to which we’re all involved in selling.

It may not be the traditional view of selling, but we’re all in sales: we’re all in the business of persuading, convincing, and influencing others.

So how do you sell in a way that genuinely serves others while bringing out the best in yourself? How might you build trust in yourself as you navigate the nos on the way to the yeses? How can you build a high-performance sales culture that priorities humanity over quotas?

We explored these questions and more with Jordan Benjamin, founder of My Core OS, one of the top 15 global sales reps for Hubspot, and is an investor with the Denver Angels supporting Colorado-based startups. Jordan is also the host of the Peak Performance Selling podcast, where he interviews sales leaders about the strategies and tactics top performers use to not only sell effectively but to manage their life better too, building resilience, empathy, and success. 

Whether you’re a seasoned sales leader or someone who finds sales cringy, you’ll want to give this episode a listen as it’s full of insights that put empathy and service at both the heart of sales and leadership.

Overview of Episode 43: Sonder and Sales with Jordan Benjamin

Talking Points

  • Why Jordan cares about human operating systems and how he brings that into sales culture
  • The changing nature of sales and the buyer’s experience
  • Why salespeople have to lean hard into skills like empathy and building trust to overcome the used car salesperson stereotype
  • Why trust is the true currency that we all have
  • Why trust is hard to build in the sales process
  • Why sonder is one of Jordan’s favorite concepts
  • How mindset helps leaders and salespeople lead with trust
  • Practices that have helped Jordan build trust in himself
  • Practical ways to play the long game, even in tough times
  • The power of a helping hand
  • A yoga mindset hack that Jordan loves and has helped him in other areas of his life
  • Reframing things as your practice and setting aside comparisons to others
  • The role of vulnerability in sales and leadership


“Sales has to move much more from always be selling to always be helping.” – Jordan Benjamin

“How I build trust in sales and how I actually help my prospects is by understanding the space in a really good way by learning as much as I can and then actually focusing on helping or even telling folks that they’re not a good fit for what I’m trying to sell.” – Jordan Benjamin

“It’s this really challenging struggle against our innate desire to solve for ourselves as humans. But to realize if we can actually move to solving for others, leading with this concept of how can I help, we’re actually going to create the biggest impact and help the most people.” – Jordan Benjamin

“Trust is the true currency that we all have, as individuals and as businesses.  Do we do and deliver on the things that we say we’re going to do? And do we do that with credibility, with honesty, and with integrity?” – Jordan Benjamin

“The concept of sonder has helped me work to build trust with my prospects, with the folks that I engage, with the people that I coach, and the clients that I work with because we all have our own struggles. We are all humans that have flaws that have challenges.” – Jordan Benjamin

“As you think about an entrepreneur getting started, or working on your own project, or a leader, it’s really about leading with trust, I think we’ve been conditioned to live in the state of fear as humans that’s kept us alive. It’s an awesome thing. But fight or flight is not serving us in today’s day and age. So moving to this concept of how do we lead with more trust, opposed to leading with no trust at all, is something that I try to really focus on. It takes a lot of hard work because I’ve got a bunch of baggage that makes me not trust people,  and so do most of us, which helps me realize that with others and really show up as this authentic human.” – Jordan Benjamin

“Giving me a no is better than just not saying anything because those nos allow me to move on to the next person that might say yes.” – Jordan Benjamin

“It all starts with that concept of trust, with that concept of empathy and understanding. What is it that I have that I can bring to the table? How do I actually build that relationship?” – Jordan Benjamin

“This concept of building these relationships is what we really strive for and thrive on as humans.” – Jordan Benjamin

“Vulnerability is the key to true growth and real authenticity and how we work and how we lead our teams.” – Jordan Benjamin

This episode sponsored by:

The Future Is Trust

Embracing the Era of Trust-Centered Leadership

There’s a lot of uncertainty about the future, but one thing we are sure about is that The Future Is Trust. Which also happens to be the title of our new book that’s available now: The Future is Trust: Embracing the Era of Trust-Centered Leadership.

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  • Why Trust: Why now, what’s changed, and what do we have without trust?
  • What is Trust: The act of trusting–how it inspires belonging, resilience, and collaboration.
  • How to Build Trust: Starting with ourselves, the foundational tools to wire all of our connections for trust. 

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