20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box.

In Today’s Episode with Lori Jimenez We Discuss:

1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook:

• How Lori made her foray into the world of sales at the age of 15?

• What are 1-2 of Lori’s biggest takeaways from her time at Google, Facebook and Box?

• What does Lori know now that she wishes she had known at the start of her career in sales?

2. The Sales Playbook: What, When and How:

• How does Lori define the “sales playbook”? What is it not?

• Should the founder be the one to create the sales playbook?

• When is the right time for founders to make their first sales hires?

• What is the right profile for the first sales hires?

• Should founders hire 2 sales reps at a time? What are the pros and cons?

3. The Hiring Process: Building the Sales Team:

• How does Lori structure the hiring process for all new sales hires?

• What are the must-ask questions to ask in every sales hiring meeting?

• What are the biggest red flags founders should look for when hiring for sales?

• What are Lori’s biggest lessons on how to navigate compensation discussions with potential sales hires?

• What are Lori’s biggest lessons on what title negotiation says about a candidate?

• What are the single biggest mistakes founders make when hiring for sales teams?

4. Scaling the Machine: Bringing the Dollars In:

• How does Lori approach discounting? When is the right time to do it?

• Is old-school enterprise sales and entertaining dead? How has it changed?

• How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal?

• How does Lori approach multi-year deals? What is good? What is bad?