March 5, 2022

Jake Dunlap, CEO & Founder of Skaled | Cold Calling, Side Hustles & Terrible Marketing

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➡️ About The Guest⁣

Jake is the CEO and Founder of Skaled, a consultancy focused on helping global 2000 companies and start-ups grow by optimizing their sales process, people, and technology with customized, repeatable, and sustainable strategies.

Prior to Skaled, Jake headed Sales & Customer Success for Chartbeat. Within the first nine months of his tenure, he grew annual bookings by more than 300 percent year-over-year and nearly doubled monthly recurring revenue.

Before that, Jake was the VP of Sales at Glassdoor, where he expanded the department from one to 40 employees and grew employer-direct revenue from $0 to nearly $1 million in monthly recurring revenue.

Since launching Skaled in 2013, Jake has been a sought-after industry thought leader, quoted by Forbes, Inc., and Huffington Post.


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➡️ Talking Points⁣        

00:00 - Intro

03:14 - Jake Dunlap’s Origin Story.

04:52 - What Was The Thing Which Pushed Jake Into Telemarketing?

06:10 - How Does Jake Get Quick Wins?

08:38 - What Was The First Job Jake Took?

10:00 - Oldschool Sales & Marketing Strategies.

14:05 - Sales Process In 2010 Versus Now. 

16:16 - Is Sales Dependent On Technology?

19:19 - Jake’s Most Impressive Career Roles. 

21:57 - Jakes Mission In Life.

23:12 - When Jake Doubled Down on Entrepreneurship.

24:16 - What Does The Modern Sale Organization Lack? 

26:34 - “Sales Are Not Relationship Building In 2021” - What Does This Mean?

29:24 - Framing Things Differently.

32:35 - Lowering The Minimums Instead Of Tracking The Activities.

35:10 - Is Jake’s Team Still Cold Calling?

39:42 - Why Are Marketers Not That Creative? 

42:16 - Why Everybody Has A Side Hustle When They Are Young?

44:31 - What Is the Difference Between Inbound And Outbound Sales?

47:30 - Building Your Own Brand Is A Good Use Of Time.

51:28 - Some Advice For Salespeople.

53:06 - Where Do People Connect With Jake? 

53:23 - What Was The Biggest Challenge Of Jake’s Career And How Did He Overcome It?

54:00 - How To Hire & Onboard New Employees?

55:57 - Who Is Jake’s Mentor?

57:34 - Jake’s Book Or Podcast Recommendation.

59:44 - What Would Jake Dunlap Tell His 20 Year Self?

1:00:33 - What Does Success Means To Jake Dunlap?

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