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20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

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Aug 17, 2022

Jordan Van Horn, a Revenue Leader at Monte Carlo with impressive stints at Segment and Dropbox, shares his journey from the wine industry to tech sales. He emphasizes that success in sales isn't just about pricing or revenue in the early days but optimizing for long-term relationships. Jordan discusses the importance of a well-defined sales playbook and when to hire sales leaders versus representatives. He also highlights insights on effective onboarding and the necessity of learning from past sales experiences to foster a high-performing team.

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ANECDOTE

Unexpected Start in Wine Sales

Jordan Van Horn's sales career began unexpectedly in the wine industry, selling to diverse groups like grocery store managers and US senators.
This experience taught him valuable lessons in connecting with people from different walks of life and understanding their priorities.

INSIGHT

Key Learnings from Dropbox and Segment

At Dropbox, Van Horn learned the critical importance of simplicity and clarity for startups, noting their struggles with identity.
At Segment, he highlighted the value of hiring top talent, recognizing a company's true strength lies in its people and culture.

ADVICE

Founders' Role in Sales Playbook

Founders should create the initial sales playbook, focusing on three core elements: target customer, key wins/losses, and immediate buying reasons.
This initial version should be simple and open-ended, allowing for evolution as the company grows.

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Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.

In Today's Episode with Jordan Van Horn We Discuss:

1.) Entry into the World of Sales:

How did Jordan make his way into the world of sales first with a vineyard?
What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset?
What does Jordan know now that he wishes he had known when he entered sales?

2.) The Sales Playbook:

How does Jordan define "the sales playbook"? What is it not?
What five core things should the sales playbook help you accomplish?
Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales?
How does Jordan advise founders on three signals that now is the right time to bring in a sales hire?
How does Jordan advise founders on whether the first sales hire should be a rep or a leader?

3.) The Secrets to Pricing and Discounting:

Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for?
When does price discipline become important in a company journey? What are the dangers of not having price discipline?
What two tools do sales leaders have to use in order to create urgency in a deal closing process?
How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?

4.) The Hiring Process:

How does Jordan structure the hiring process for all new sales hires?
What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers?
Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for?
Does Jordan use case studies with candidates? What makes the best? What makes the worst?

5.) The Onboarding:

What is the ideal onboarding process for new sales reps?
What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready?
What are some early signs that a new hire is not working out? How do we measure their impact?
For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?