Enterprise Sales Development with Rob Simmons


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By Eric Quanstrom and Caroline Maloney, Eric Quanstrom, and Caroline Maloney. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.
In this episode of Enterprise Sales Development podcast, we speak with Rob Simmons, VP of Sales Development at LeanData. Rob talks about entering into his role where he leads 20+ SDRs after first being a customer. He discusses how he scaled his team and is responsible for a lot of the growth. He also shares how his experience as a football coach informs his leadership style and his approach to coaching and leadership today.

  • His experience as a coach and his transition from coaching into sales
  • How his coaching experiences carry overs into his leadership in sales
  • His thoughts on employee retention
  • The Four C’s he looks for when hiring
  • The most important thing when onboarding and training a new SDR
  • Suggestions for certifications and things an SDR can do prior to the interview process
  • Takeaways from his time at Outreach
  • Using proof points and what the narrative arc looks like at LeanData
  • Sales methodologies that he finds incredibly valuable as well as disciplines and coaching skills he looks to instill to his team
  • How he coaches reps to take really hard objections and how he straightens the SDR/AE relationship

  • “I do love people who come from a team sports background. I think it just breeds the right kind of culture of competitiveness, but not at the expense of others. Like ‘We’re a team here together and we can help each other and all be successful together’ is very much the culture I try to instill within my teams.” - Rob Simmons [10:50]
  • “I’ve realized that you can find SDRs within any background whatsoever, and it’s more about the intangibles that they have.” - Rob Simmons [12:06]
  • “The phone still works. And I’m a big preacher of leaving voicemails, even if you don’t catch people.” - Rob Simmons [20:21]
  • “Alway be practicing, but you just got to pick up the phone and go.” - Rob Simmons [31:51]
  • “You always, no matter what it is, want to show what good looks like.” - Rob Simmons [41:13]

  • [00:00] Intro
  • [00:29] Meet Rob Simmons
  • [01:53] Scaling sales development and employee retention
  • [06:54] His team of SDRs
  • [08:26] His experience as a coach
  • [11:20] The Four C’s
  • [14:21] Onboarding and training a new SDR
  • [16:46] Takeaways from his time at Outreach
  • [22:01] Proof points and what the narrative arc looks like
  • [29:03] Sales methodologies
  • [31:59] Disciplines and coaching skills he instills to his team
  • [36:18] Working with hard objections
  • [39:18] Eye-opening responses
  • [41:23] Straightening the SDR/AE relationship
  • [46:08] How to contact Rob



56 episodes