When to layer Enterprise sales on PLG with Maggie Hott (OpenAI Head of GTM)

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Maggie Hott was part of Slack’s hypergrowth period, starting as the founding Account Executive. She helped grow Slack from less than $15M to over $1B ARR.

Maggie repeated her magic as Senior Director of Sales at Webflow. She scaled the company from $60m to $100m ARR before joining Open AI as Head of Go-To-Market (GTM).

In The SaaS Operator newsletter from 12th March 2024, you’ll learn:

  • How to build your first sales team.
  • Selling to SMBs vs Enterprise customers.
  • When to layer on sales to your PLG motion.

If you’ve been thinking about adding enterprise sales to achieve your scale-up dreams, you’re not alone. Many top PLG SaaS companies, like Slack, Miro, and Notion, have sales teams dedicated to enterprise clients.

And Maggie Hott has pulled it off…twice.

We dug up her strategies and tips for layering sales on PLG in one spot.

When To Add Sales To Your PLG Motion

Maggie points out 4 signs to know you’re ready to layer on Sales:

  1. You understand the pain point your product solves.
  2. You’re generating about $1-2 million ARR.
  3. You have product market fit or are close to it. (This is tied to #2)
  4. You are able to sell to companies outside your close network. E.g., friends and family.

When these signs start showing, it’s time to think of your first sales hires. 👇🏽

👨‍💼 Building Your First Sales Team

Use Maggie’s tips to help you set up an effective first sales team.

Who to Hire

There are 2 kinds of people to hire:

An Account Executive at a hyper-growth startup with proven sales experience. They have the practical know-how to do the dirty work in a startup environment. Ideal for getting your sales up and running.

A salesperson who has recently moved into a management role. Aside from the practical know-how, they have experience managing a small sales team. It’s easy to promote them to higher sales leadership roles with little training as you scale.

Regardless of which one you hire, look out for these traits:

  • Experience managing a team.
  • Experience doing the “dirty work” in sales.
  • Comfortable with ambiguity: Startups experience constant changes in direction, strategy, goals, etc. The right salesperson must be okay with this rollercoaster environment.
  • Team player: She is a collaborator who loves to put the customer and company first.

Who NOT to Hire

Head of Sales: It’s your early days with sales. Figuring out your sales goals, compensation plan, etc will take time. Until then, you won’t know what criteria to hire your Head of Sales with.

Also, because it’s a managerial role, many Heads of Sales are far removed from the actual groundwork. Hiring someone who isn’t ready to get dirty with cold outreach will slow your sales growth. Plus, they’re very expensive.

Selling to SMBs vs Enterprise Clients

The Wrong Way

This is how most PLG companies think enterprise sales works. 👇🏽

❌ Targeting high ACV (Annual Contract Value) clients with the same self-serve product and pricing model offered to SMBs.

Some PLG companies try to solve this by adding a new tier that offers more seats at a higher price.

But enterprise clients don’t care about the same thing that self-serve customers do.

If there’s almost no difference between your new tier and the existing self-serve product, big clients won’t buy it.

The Right Way

The key to dealing with enterprise clients vs SMBs is to differentiate your product offering.

✔ If you want to sell to high ACV clients in the future, start thinking of ways to make your enterprise product different and superior to your self-serve product…before you even reach that point.

Here are Maggie’s top features to differentiate your Enterprise product:

  • Advanced Security
  • Single sign-on (SSO) Authentication
  • Data Processing Agreement (DPA)
  • Master Service Agreement (MSA) and Service Level Agreement (SLA)
  • Dedicated Customer Success Managers
  • Mobile Device Management (MDM)
  • 24/7 Live Support
  • Data Loss Prevention (DLP)

There it is—a complete working playbook for layering on sales to your PLG motion. Look out for the right time to layer on sales, and once you do, hire the right people to start with. You’ll have a higher chance of your outbound sales being successful.

If you enjoyed this, you would love our newsletter, The SaaS Operator. It’s a weekly newsletter where we share actionable tips from SaaS experts to help you grow your MRR. Subscribe at www.earlynode.com.

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