Segment.com's VP of Business on How to Succeed in Sales

How does a world-traveling bicyclist/activist/corporate lawyer/nonprofit founder go from being a junior BDR to a VP of Business within a few years? Not how you’d think.

Raphael Parker is the VP of Business at Segment, an up-and-coming customer data startup backed by Y Combinator. In this interview, Steli and Raphael talk about selling to executives, the power of now, the traits of super-successful salespeople, recruiting internal champions, shortening your sales cycle, and why you should stop chasing that promotion.

From Bicyclist to VP of Business

David Greenberger, the former National Director of Sales for Foursquare, said no one grows up wanting to be a salesperson—an observation Raphael knows all too well, as his chatty nature had him pegged as a potential lawyer at an early age.

However, his first itch for sales began on a New York subway.

While pitching the importance of elections to hundreds of subway commuters and registering them as voters began as a spontaneous decision, the thrill of pitching prompted him to begin registering voters on the subway each day until he eventually quit his office job to bicycle down to Florida and register more voters.

Since then, Raphael has founded a nonprofit, graduated from law school, worked as a corporate lawyer, quit his job, traveled the world on a bicycle and left everything behind to become an entry-level BDR.

After a year of developing his skills at his first sales job, he became Segment’s first full-time hire: their VP of Business.

Here are the keys to Raphael’s rapid success.

The Driving Force Behind Successful Salespeople

Successful salespeople aren’t just competitive. To them, sales are more about providing insane value than topping last month’s metrics.

The most successful salespeople are product evangelists who believe in the value of their solution so deeply that they are hurt when they see businesses struggling unnecessarily.

If you want to join the ranks of the super-successful, shift your primary focus from improving your numbers to providing more value.

Stop Chasing That Promotion

To dominate startup sales, focus on improvement, not promotion. Instead of asking, “How can I move up?” ask, “What am I doing today, and how can I master it?”

Many salespeople try to rush out of being an SDR and into a more senior role, only to find themselves totally unprepared when they get there.

Additionally, many VPs miss out on their responsibilities in their old roles. A VP of Sales does very little actual selling. So, if you love the act of selling, that new promotion might be a mixed blessing.

Take full advantage of the moment you’re in and your position. Make mistakes while the stakes are low, and learn everything before moving on. That’s true whether you’re an SDR, a sales manager, or a founder.

Shorten Your Sales Cycle with These 3 Questions

The longer your sales cycle, the higher your customer acquisition costs (CAC). Answer these three questions as early as possible to shorten your sales cycle (and lower your CAC).

1. What Challenge Does Our Product Solve?

Ensure that your prospects have a legitimate problem and that your product is a valuable solution to that problem. Selling to the wrong customers will kill your business, so always qualify early.

2. How Can We Quantify Our Solution?

Your solution should be something that can be (and has been) calculated. For example, does your product:

• Do the job of three developers?
• Save 60 minutes a day?
• Cut marketing costs by 30 percent?

You need a performance metric to prove the effectiveness of your product and give your customers something to benchmark against.

3. What Could Happen in the Coming Months That Would Expedite the Sales Process?

Urgency is a powerful sales tool. Is there something that might come up soon that would make your prospect need your product? If so, remind them that being proactive is better than reactive.

Don’t be pushy; say, “I noticed X, Y, and Z. I’ve seen this happen before, and I don’t want you to go through it. Here’s how we can avoid that.”

How to Identify and Recruit an Internal Champion

You need an internal champion in enterprise sales. Ideally, this person will:

• Be a company stakeholder
• Have a meaningful voice in discussions
• And, most importantly, have a problem that you can solve

Once you’ve identified this person, be upfront. Say, “I noticed you have this problem, and I know we can help you solve that. Help us help you.”

If you have a genuine solution to their problem and the company’s problem, they will become your internal champion. As soon as you’ve got that, the whole process becomes much easier (but don’t let your guard down; you sell to decision-makers, not internal champions).

Patching Your Sales Process

Think of your sales process as a product. It will undergo many updates over time. What you have today isn’t (and shouldn’t be) the final version. As your business grows, be prepared to update your sales process.

Here’s a rough guide to the first three “versions” of sales.

Sales 1.0: $0–$1M Annual Revenue

In version 1.0, you’re still finding a product people want to spend money on and a market willing to spend money. At this point, you should be:

• Making an ideal customer profile
• Creating your sales documentation
• Using sales as a market validation tool

Sales 2.0: $1M–$2M Annual Revenue

In version 2.0, you must focus on building a predictable and scalable sales process. That means you should be able to:

• Accurately predict your revenue at least three months in advance
• Hire more salespeople or add additional revenue without needing a complete overhaul

Sales 3.0: $2M–$10M

In version 3.0, you should be scaling your model. Use everything you created earlier to:

• Hire more salespeople
• Add new management positions (sales managers, VP of Sales, etc.)
• Explore new markets

There will be many patches between those three versions (v1.3, v2.7, etc.…), as well as many versions after them. Your sales cycle is a constantly growing, evolving process. Treat it that way, and you won’t have much trouble.

How to Deal with Enterprise Leads Gone Cold

If a promising enterprise account suddenly stops responding to your emails, it can be tempting to kick your follow-up into overdrive. But when you become desperate, you’re saying, “My time isn’t valuable,” and you’ll be treated that way.

Instead of letting enterprise accounts string you along, be the one to walk away. Send a breakup email saying something like,:

If that doesn’t get their attention, nothing will. Move on to more promising prospects, at least for a while.

Customize Your Email Campaigns to Your Customers

Your drip email campaign should focus on providing as much value as possible.

That means knowing your customers' personal and professional values, interests, and needs.

For example, if you notice that their LinkedIn profile has a photo of them fishing, email them, “Hey, I stumbled across this article on the 12 best fishing locations in the US. Have you been to any of them?”

Do anything to prove to your customers that you know them, care about them, and can provide value. Ultimately, the business that knows the customer best will own them.

How to Divide Territories Within a New Sales Team

Figuring out a way to divide up sales territories is tough, especially in the beginning.

Raphael’s market was the entire country, and he had to split it between six sales reps.

His first attempt involved dividing the country into East and West territories, and then splitting businesses among his sales team by the first letter of the company.

That meant one rep had West A through H; another had West I through P, and so on.

This changed when Raphael started tracking the sales data of his salespeople and learned their strengths and weaknesses.

His second (and current) attempt at division is based more heavily on his salespeople's skills and preferences. Those who sell most effectively to startups handle startup sales, and the enterprise specialists handle enterprise accounts.

Just like you should know your customers, you must also know your salespeople.

Raphael’s Secret to Success

According to Raphael, success comes down to Mastering the moment. Here at Close, we call that the power of right now.

It means knowing where you want to go but treating this moment as a valuable step in the journey.

Whether you’re a junior SDR or a VP of Sales, mistakes are always to be made, and lessons are to be learned. Take a look at where you are today. What can you do today to master the moment?

Now, get out there and crush it.