GTM 10: How to Sell to the Enterprise

GTM 10: How to Sell to the Enterprise

In this week’s episode, we are joined by Chris Donato who shares his journey: lessons, losses, and wins in the Sales profession. Chris is the CEO of Esellas, a company that helps salespeople sell.

He discusses finding purpose in work, taking big risks in sales, and some lessons in his career. Chris shares stories from his experiences in turning a napkin idea into a $300-million contract, losing an $850-million deal, being instinctive in making business partnerships, being strategic in attempting to make a sale, and so much more.

In this episode, you will learn:

  • How to find purpose and create meaning in your work
  • How and when to take big risks in sales
  • How to transition from mid-market to enterprise


(0:57) Introduction

(1:27) Why is there a drop in Gen Z workforce participation?

(4:30) Finding purpose in work

(9:05) A napkin idea worth $300 million 

(14:50) How to turn a business problem into an opportunity

(20:45) Does it get easier to take big risks?

(22:44) What would Chris do differently now?

(25:50) Using relationship mapping to your advantage

(27:55) How to transition from mid-market to enterprise

(31:40) Lessons from a career in sales


The joy is in the process, not the outcome.

People should define purpose and take accountability for it.

Whether you’ve originated an opportunity or the opportunity has come to you, be deliberate. When you decide to pursue something, be clear. You have a real chance to make a difference for that customer, not just to win it but to make a difference.

People need to feel like they’re doing something that is going to contribute to the greater good and if your business isn’t drawing a correlation to something that’s greater than itself than profit, you have a problem.

Selling is never a straight line.

If you can figure out how to make people successful, make the money, and improve their business, the conversation changes.

If you want not just a name but to make an impact, you’ve got to bet big and think big.

The GTM Podcast

Don’t miss The .GTM Podcast dropping every Tuesday, discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

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Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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