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How to Get Your First Customers and Hire for Sales

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Most early-stage startups hire salespeople way too early.

In this world of rapid iteration, the impetus to hire your first salesperson is huge. Many founders assume that their product will only achieve a product-market fit with customer input and that salespeople are a requirement to landing customers.

While your first couple of hires might be engineers, you should probably hire a salesperson pretty quickly, right?


In reality, you shouldn’t hire a salesperson, but a sales leader or manager, right?

Double Wrong.

The first sales hire is an incredibly crucial role that can make or break your startup — but it shouldn’t be the first move. I break it down into two parts:

  1. Getting your first customers (the prerequisite)
  2. Hiring your Sales Ninja

I’ll explain how we did both of those at Bloomreach en route to raising $97M and growing to 280 employees.

Get your first customers (by any means necessary)

In the early days of product iteration, you need to get customers involved to validate the problem and iterate on the solution.

At BloomReach, we launched our first pilot customer in July 2009, not even three months after we’d established our four-person engineering team. Signing up an early customer was an essential way to drive towards execution and away from speculative debate. It clarified priorities in a way that nothing else could have. Over the course of 2009, we signed up five-plus pilots, monetizing our first paying customer in November 2009.

How to get those first customers

Your first customers will likely be early adopters (more on that shortly).

But without a sales team, who lands those early clients? You do. No salesperson worth his or her salt is interested in selling your half-baked idea with little-to-no cash incentive, so you (the founders) or your product manager (general business person) land them.

It’s the responsibility of the founders and the early team to get the first 5-7 customers. There are many ways to do that, but the criteria is simple: by any means necessary. You cold call. You show up in potential customers’ lobbies. You use your school ties. You do anything and everything to get meetings with the right people. Generally, I’ve found these three channels to be the most effective:

1. Networks

In the early days of BloomReach, we found our first few customers through our networks. I or another early team member would tap our network and say “Hey, can you introduce me to ___ person? I just want to have a conversation about testing my idea.”

People were often willing to take a conversation if they felt like they’re not being sold to, so I’d use my network to find ways of simply getting in front of people. If the pitch is good enough, that other person will naturally say, “Hey, let’s continue this conversation,” and then you know you’re onto something. At this stage, it’s especially important not to approach them saying, “I want to sell you something.”

2. Trade shows

The second strategy is appearing at trade shows. Since this can be hard when you have no credibility, my colleague, Will Uppington, stood in the lobby of one tradeshow and approached people as they entered and exited. It saved us the cost of attending and led to an early customer, Walgreens, essentially just happening upon us.

3. Supporting networks

The third is to leverage any of your infrastructural support networks. VCs and advisors can be early introductions to customers. Many of them may just be doing you a favor, but that’s okay. They’re on your team.

If you have a good proposition and method of getting in front of people, you’ll need a compelling way of expressing what you’re building. The first people willing to work with you will be early adopters. They’re a specific breed, so you want to be ready to meet them where they are.

How to pitch early adopters

For early adopters, buying your product is not an economic decision. They want to be heroes who are ahead of the curve; if they don’t match that description, they’re (by definition) not early adopters.

My first sales pitch to our first client went something like this:

We’re building an amazing technology. If it works, it will transform your business in the following X ways. By the way, there’s no guarantee it works, but . . .  we have 5 of the smartest engineers in the world working on it, and I can promise you that we’re going to work our ass off. We’re going to be thinking exclusively about your success. If it works, you’re going to be a hero, creating an industry-defining transformation in your business. How do you feel about five of the smartest engineers from Google thinking about your business, optimizing it, and delivering value? And we won’t stop until it succeeds. That’s the commitment I can make to you.

Lots of customers appreciate the authenticity in that sort of honest pitch. Early adopters know there’s a risk and are okay with no guarantees. They’re just so used to being sold to that authenticity appeals to them.

Test your messaging

Once you get early adopters, use them to better understand your business. I remember talking to a friend of mine who built a multi-billion dollar SaaS company. As the product was iterating, he literally acted like a sales development rep, cold-calling and trying different messaging. He was calling around not just to get clients: he was testing his crisp messaging in the form of a 30-second pitch.

Ultimately, that had a huge impact on more than just signing early clients. It impacted the product since it crystalized what the customer really valued in terms of the core message. By pitching, you learn about the product’s viability, which is often a lot more valuable than the transactional value of a sale.

As a founder, you need to close the first set of customers. If you can’t, then you might not have the right early team.

Making your first sales hire: the Sales Ninja

You’ve closed your first few customers and iterated with them to find product/market fit. You’re ready to expand. Now you need a Sales Ninja.

As Historian Hanawa Hokinoichi writes of the Ninja’s key role:

“They traveled in disguise to judge the situation of the enemy, they would inveigle their way in the midst of the enemy to discover gaps, and enter enemy castles… always in secret.”

This is in contrast to the better known Samurai. Samurais are defined by their strict rules of honor and combat, much more akin to the “scaling-oriented” salespeople you will need later.

What to look for in a Sales Ninja

The Sales Ninja is a special role that requires the right type of person and skill set. I’ve found that regardless of vertical or company, the following traits remain essential for a Sales Ninja.

1. Curiosity

One word should sum up your ideal Sales Ninja: Curiosity.

If you meet a candidate who says, “Tell me how to sell it: what’s the addressable market and the ASP?” — you’ve got the wrong person. But if they say, “Explain to me how the product works and show me which customers signed up and which didn’t,” they just might be a Ninja.

Sales Ninjas probe. They ask a lot of questions and come to their own conclusions. You can often see their wheels turning as they try to figure out the ideal client and piece together a strategy.

Sales Ninjas are almost always:

  • Smart, inquisitive, and highly curious
  • Naturally open-minded and always experimenting
  • Inclined towards approaching every sale as a problem-solving exercise

2. Versatility

Sales Ninjas feel like 1/3 product manager, 1/3 BD person, and yet they still have the closing instincts to be in sales (the final 1/3). They understand the product pretty well, but they’re continuously discovering what resonates with the customer that will lead to a sale.

They’re closing deals by figuring it out as they go.

A Sales Ninja is usually the person who worked on a new product, new market segment, or new proposition at their previous companies. That versatile experience is ideal for selling your early-stage product.

3. Ruthless closing

A true Sales Ninja will close a deal using any method necessary.

They have an intense, vicious, anything-to-win skill set that can compensate for an early product’s limitations, marketing difficulties, and the lack of go-to-market definition.

They don’t need to have a technical background. They do, however, need to be technically curious and not have a fear of technology or learning. Those fears make it difficult to do this job since being a good Sales Ninja is about asking the right questions.

4. Ability to work with product

An ideal Sales Ninja should put pressure on the product team, finding tension points the engineers don’t notice. At Bloomreach, we had a product driven by a team of engineers. It was AI and machine learning, essentially a black box that did its magic in the background. From the perspective of an engineer, a black box is the right answer.

Where that collides with reality: to trust a machine, humans want to know what the machine is doing. The product team solved the engineering problem, but a Sales Ninja understands the emotional buy-in that a customer requires. In our case, we added visibility capabilities that positively influenced the product.

Without a Ninja in place to understand that need and then persuade the engineers, we wouldn’t have developed our product in a way that resonated with more customers.

Scaling the team: Ninjas vs. Samurais

Once the Ninja develops the formula, you need more salespeople to execute on it.

If a Ninja can bob and weave their way through a sales process to close a deal — doing it differently this time, next time, and the time after that — why wouldn’t you only hire Ninjas?

Imagine you now want multiple salespeople: a sales development team of 10, 15, 20. You want a well-understood recipe that you lead people through. In the language of the Samurai, you need a code. A Ninja might do an effective job at defining that code, but they typically won’t be a good person to lead or follow a code. It’s just not who they are.

Ninjas don’t make great leaders. They’re often loaners, figuring out answers on their own. If you’re building a team, you need a leader. You need someone to be the bridge between the customer’s success, the sales team’s success, and the company’s success. A samurai enforces a code that keeps all these relationships strong.

A Samurai will typically come in and say, “I need a clear definition of a process. I expect X from marketing, Y from product, Z amount of funding, and this sort of skill set and recruiting team.” Unlike a Ninja, they’re a scaling-oriented individual, so they demand a scalable blueprint for success.

How I Hired my Sales Ninja

I met Hank at a tapas restaurant in Mountain View and knew by the end of lunch that he was the right guy for us.

He was charismatic, asked a ton of incisive product-oriented questions. He was not initially focused on the compensation or the position. He was excited about the problem. He was excited about the technology. And he was ready to bet on his own ability to take an immature technology to market.

He was a player/coach – happy to coach, but unafraid to play.

He didn’t have many questions for me about the sales process (good, because we did not have any) or about average deal size. Fundamentally, he understood that it was his job to create those, not to expect those out of an early stage startup.

He was all about creative solutions to problems.  He was inherently optimistic. He really focused on the key people involved and was motivated by market creation.

At the same time, he was a salesperson, not a product manager.  He knew how to qualify, how to probe and how to lead a customer to a logical conclusion that ours was the product to buy. And he was not afraid to talk about money.

Under Hank’s sales leadership, we built a 5 person team and grew into a position to raise our $25M series C.

Conclusion: build a “we-win” company

Technical founders typically make one of the two false assumptions:

  • “If I build a great product, I don’t need salespeople.”
  • “A great salesperson can sell any product.”

Neither of those extremes is true. Salespeople are neither unimportant nor saviors. Achieving market success is about a collaborative relationship between your early sales hires and executives.

As a leader, how do you create this collaborative relationship? It’s about setting up the company culture. You want to create a “we” orientation, where it doesn’t matter if I do my job well or you do your job well; the only thing that matters is if we win.

If it’s a we-win kind of place, teams are naturally empathetic to what the other team is facing. People embrace conflict and difference-of-opinion in the spirit of achieving a better outcome — such as with product/engineering and sales.

When you build that culture from day one, you can follow this formula to close your own deals, find a Ninja to set things up properly, and then use your team of trained Samurais to take the market by storm.

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Raj brought 10 years of enterprise and entrepreneurial experience with him when he co-founded BloomReach. Before launching the company, he was entrepreneur-in-residence at Mohr-Davidow Ventures. Prior to that, Raj served as Cisco’s director of product marketing and was on the founding team of telecom company FirstMark/LambdaNet, which grew to $80 million in run-rate revenue.

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