20 Sales: Webflow’s Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

Posted on 14th December 2022 by Harry

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners.

In Today’s Episode with Maggie Hott We Discuss:

1. The Cold Email that Led to a World-Class Sales Career:

  • How a cold email to Kevin Hartz @ Eventbrite led to Maggie’s career in sales?
  • What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset?
  • What does Maggie know now that she wishes she had known when she entered sales?

2. The Sales Playbook: PLG and Enterprise:

  • How does Maggie define the sales playbook? What is it? What is it not?
  • Is it possible for early-stage companies to do both enterprise and PLG at the same time?
  • When is the right time to add enterprise to a PLG motion?
  • What are the steps to build an outbound sales engine in enterprise? Where do many go wrong?

3. Building the Bench: Hiring Your First Sales Team:

  • Should founders look to hire a Senior Head of Sales first or a more junior sales rep?
  • Should they be hired one at a time? What are the benefits of hiring many at the same time?
  • What is the right process to hire your first sales hire?
  • What are the core traits and habits that make the first 10x sales hire?
  • What are the right questions to ask to unveil those characteristics?

4. Making the Machine Work: The Process:

  • What can sales leaders do to proactively build relationships with other parts of the org?
  • How can more junior sales reps build relationships with other functions?
  • Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound?
  • Why is it dangerous to make your self-serve product too good?

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