20 Sales: How To Interview Sales People; The Red Flags and What to Look For, How Sales Leaders Should Change Goals and Quotas in Harder Markets and What Reps Can Do To Ensure They Hit Their Numbers in These Markets with Eleanor Dorfman, Sales Leader @ Ret


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Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company’s customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering.

In Today's Episode with Eleanor Dorfman We Discuss:

1.) Entry into Sales from Working with the US Education Department:

  • How did Eleanor get her first role as an unpaid intern at Clever?
  • What are 1-2 of her biggest takeaways from her time at Segment?
  • What are the biggest advantages of sales reps having experience in customer success?

2.) The Sales Playbook:

  • How does Eleanor define, "a sales playbook"? When does it need to be created?
  • Does it need to be the founder who creates it or can it be a Head of Sales?
  • Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook?
  • How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion?

3.) Who, What and When: Building the Sales Team

  • Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two's?
  • How does Eleanor structure the hiring process for all new sales team recruits?
  • What are the clearest signals of 10x sales hires? What are red flags in the interview process?
  • How does Eleanor use demo's and case studies to determine technical ability?

4.) The First 30, 60 and 90 Days: The Onboarding:

  • What is the right structure for all new sales hires to be onboarded?
  • Why does Eleanor believe you will always hire your Head of Sales Enablement too late?
  • What are the signs that now is the right time to hire your Head of Sales Enablement?
  • What tools, materials and resources can founders provide to shorten the ramp time for new AEs?
  • What are the single biggest mistakes founders make in the onboarding of new sales reps?