Mark Goldberger is Head of Enterprise Sales at Ramp, the fastest-growing corporate card and bill payment software in America, and recently named Most Innovative Company in North America by Fast Company. Prior to joining Ramp, Mark was the first enterprise rep at TripActions (now Navan), where he helped bring in more than $100m of ARR as an IC and sales leader. Before TripActions, Mark worked at Highfive, a video conferencing company since acquired by Dialpad.

1. From Wine Industry to Sales Leader:

• How Mark made his way into the world of enterprise sales having been in the wine industry?
• Mark sent out 100 CVs for his first sales role, why did they not respond? How should companies think differently about the people they hire? What could he have done better with the outreach?
• What does Mark know now that he wishes he had known when he entered the world of sales?

2. The Sales Playbook and Why You Should Never Hire a Sales VP First:

• Why does Mark believe that you should never hire a Sales VP as the first sales hire?
• What does Mark mean when he says product-customer-fit is more important than product-market-fit?
• Why does Mark believe that revenue does not matter with your first customers? If revenue does not matter, what should you be trying to get out of them?
• When should the founder handover sales to either a junior or more senior hire?

3. How to Hire 10x Sales Teams: The Process:

• How does Mark structure the process for hiring 10x sales reps?
• What questions are most revealing in identifying a 10x sales rep? How do they respond?
• Why does Mark want candidates to pitch his own product back to him?
• How does Mark make the hiring process more challenging to really test the quality of candidates?
• What is the core difference between losers and winners in sales?

4. Discounting, Champions, Creating Urgency:

• Why does Mark not like discounting? Where do many sales teams use it poorly?
• How does Mark like to create urgency in a sales process? What works? What does not?
• How can sales reps know whether they truly have a deal champion within a buyer?
• What is the right way for sales reps to ask to meet the exec buyer?
• When is the right time to ask to meet the exec buyer?
• What are some clear signs that you are not speaking to a decision-maker?

5. Building a High-Functioning Sales Org:

• What is the right way to do deal reviews? How often? Who should be invited?
• What is the right way to do sales onboarding for all new reps?
• Why is traditional outbound still the most important thing in a sales process?
• Why do so many people get pipeline qualification so wrong?

The post 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn’t Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp appeared first on 20VC.