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

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 14 December 2022

⏱️ 64 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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?

Transcript

Click on a timestamp to play from that location

0:00.0	I will rarely ever advise you to hire ahead of sales, especially early on.
0:04.0	And here's why.
0:04.7	What a cliffhanger.
0:06.0	This is 20 sales with me, Harry Stebbings, and this is the monthly episode where we sit down
0:10.2	with the world's best sales leaders to unpack their tips, tactics and strategies to scaling
0:15.1	the best sales teams.
0:16.4	And today, I'm so excited to welcome an incredible force of energy and charisma in the form of
0:21.5	Maggie Hot. Maggie is the director of sales at Webflow, where she leads their sales
0:25.7	dev, account exec, and solution engineering orgs. And prior to Webflow, Maggie spent an
0:30.6	incredible six years at Slack in a period of real hypergrowth for the company, having joined
0:35.0	as the founding AE scaling to a senior enterprise leader.
0:38.5	Before Slack, Maggie was the founding sales hire at a Vembright.
0:41.9	And if that wasn't enough, Maggie's also an active angel investor and advisor to Cowboy Ventures,
0:46.9	Scruble Ventures, and is a founding operator and LP at Coalition Partners.
0:50.6	A huge thanks also to Danny Herzberg at Sequoia and Kai Mack for some fantastic
0:55.5	questions suggestions today. I really did so appreciate that. But before we dive into the show
1:00.2	today, planning sales force capacity and successful quota management can define the trajectory of your
1:05.4	business. That's why you need pigment. Pigment is an integrated planning platform that helps
1:10.6	sales leaders bridge the gap between
1:12.7	strategy and execution by promoting those golden conversations between your sales planning team
1:18.6	and the leadership of the reps out in the field.
1:21.2	From capacity planning and quota management to accurate territory plans and increase visibility
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from The Twenty Minute VC, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of The Twenty Minute VC and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.