20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo


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Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.

In Today's Episode with Jordan Van Horn We Discuss:

1.) Entry into the World of Sales:

  • How did Jordan make his way into the world of sales first with a vineyard?
  • What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset?
  • What does Jordan know now that he wishes he had known when he entered sales?

2.) The Sales Playbook:

  • How does Jordan define "the sales playbook"? What is it not?
  • What five core things should the sales playbook help you accomplish?
  • Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales?
  • How does Jordan advise founders on three signals that now is the right time to bring in a sales hire?
  • How does Jordan advise founders on whether the first sales hire should be a rep or a leader?

3.) The Secrets to Pricing and Discounting:

  • Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for?
  • When does price discipline become important in a company journey? What are the dangers of not having price discipline?
  • What two tools do sales leaders have to use in order to create urgency in a deal closing process?
  • How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?

4.) The Hiring Process:

  • How does Jordan structure the hiring process for all new sales hires?
  • What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers?
  • Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for?
  • Does Jordan use case studies with candidates? What makes the best? What makes the worst?

5.) The Onboarding:

  • What is the ideal onboarding process for new sales reps?
  • What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready?
  • What are some early signs that a new hire is not working out? How do we measure their impact?
  • For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?