It's time. Or is it? 

According to Paul Graham of Y Combinator, “Startups take off because the founders make them take off. There may be a handful that just grew by themselves, but usually, it takes some sort of push to get them going. A good metaphor would be the cranks that car engines had before they got electric starters. Once the engine was going, it would keep going, but there was a separate and laborious process to get it going.”


Daunting, right? It places the success (and failure) of our startup babies squarely on our quaking shoulders. Let's face it, there's no one out there who loves (and is good at) every business function there is. As a sales rep, sales engineer, and sales leader, I've gotten really good at sales. But for a number of solopreneurs out there (I'm looking at you, coders!) it remains their Achilles heel. And this is what Paul is talking about. 

Everyone in the startup ecosystem will tell you that the first person to sell your product should be you, the founder. Even if you're terrible at sales and have no sales experience and know-how. Even if you'd massively prefer being the guy who writes the code while 'others' do the selling. Early sales are where you really get to know whether your idea has a market, and if so, how much it fits your customers' needs. You want to get as close to your prospects as you can and do the customer development work yourself. 

And it doesn't need to be high stakes right away: start with your network of friends, acquaintances, co-workers, alumni, past employers and so on. I was shameless about asking for introductions, and you know what? People are amazing - I can't remember a single time when someone refused to introduce me to one of their contacts. Especially since at this stage, you aren't really selling

Early sales exploration 

This isn't the time to close deals, instead, the focus is on early-stage sales exploration. You're trying to understand and listen to your customers better and understand their pain points. You want to see, first hand, how they describe their problems, what metrics they use to measure them, and how they respond to your solution. The objections they have to your solution are invaluable to your sales and product strategies. 

This is also the time you figure out what works. You get started with cold emails, write your first phone sales scripts, and test different strategies, methods and tactics for every aspect of the sales process: from lead generation to pricing to your own sales metrics. It might take several iterations of customer feedback, tackling issues/making improvements to get to the point where your sales process starts to work consistently. Then, and only then, is it time to start thinking about hiring your first sales rep. 

The risks of going in too early 

If you don't have a robust sales model yet, the performance of your sales reps is most likely going to be hit-or-miss. You can't expect predictable sales when you haven't achieved product/market fit. Moreover, you can't expect your salespeople to not make mistakes - this is when they're experimenting (because they don't have a strategy that works yet), and that puts you in a pretty tricky spot when it comes to deciding performance standards and incentives. 

Moreover, if you've stepped away from sales, you've also cut yourself off from a lot of market intel! Your people are feeding you information about what worked and what didn't, sure. But it is second-hand and it is from their filters! Sales reps and founders do not think alike! Do you know what keeps people from buying your product? If you don't, how can you possibly train sales reps how to manage these objections? You have the vantage point to see potential (and actual) problems in your sales and business model, and how to solve them. You need to be in the room, till this work is done. 

Then, there is always the chance that you'll hire a sales mercenary. These people are great at closing deals but can be really bad for your business because they're too aggressive. These are the people who close deals that shouldn't be closed, stretch the truth (or outright lie!) and use questionable tactics. Their interest lies in earning their commission, not in the long-term viability of your business. For a young company, sales mercenaries can do serious damage to your reputation (which, when you are starting out, is everything). 

There is, of course, a flip side. You may already be doing really well. You've cracked the process, the model, the pricing, and the product, and you're able to close the larger accounts consistently, by yourself. In this case, do you need a sales rep? You might be better off with a Sales Development Representative instead. Let them do the lead generation and prospecting, and let them set up the meetings. You come in and close. It works, and SDRs' salaries are way lower than sales reps. This brings me to… 

Your options 

Your first hire need not be a sales rep. Depending on which stage your startup is in, how many sales you already have under your belt, your own bandwidth and sales experience, and your budget, there are a number of great options. 

Sales co-founder: If you're still in the early stages, you might find this to be a great option. Not only do you gain invaluable expertise from someone who is deeply invested, but there's also no salary to worry about. The co-founder has skin in the game, which means they will bring more of themselves to the business than an employee will. 

Full-time permanent salesperson: This is the next best thing. A dedicated sales rep is a big step - one person who dedicatedly focuses their time and attention towards bringing in new business. However, timing is everything. Also, depending on whether you hire experienced salespeople or newbies, the cost can become a major factor too. More on this later. 

Commission only: This can be a good option for small companies, but most experts believe that paying only on commission can cause you to lose money, instead of saving it. Also, bear in mind that commissions-only sales reps tend to be the first to cut and run when times are hard, which is when you really need the support of your sales team. 

Outsourced sales reps: This can be a great option when you're overstretched, and can't provide much oversight. The good thing here is that they have a proven process, which you can adapt to your product (and maybe even base your own internal process on). Just make sure you pick a firm that has a management structure built in, or else you're stuck micromanaging an outside team. 

Pro tip: Two is better than one. 

It sounds counterintuitive, especially when you're bootstrapped. I know. I know you're thinking of the time you'll need to invest, but that's where Equip's ready made skills assessments for sales roles can save you a ton of time. 

 How To make that critical first hire?

However, it makes a LOT of sense. Say you hire just one sales rep. They do miserably. Or they do exceptionally well. Do you know what worked? Was it your strategy, your product, the salesperson, or something else altogether? Now, if you hired two, you'd know. Two sources of feedback, two to compare and contrast, two to do A/B testing with and two sets of data points. 

Two are better than one. Especially when there are no sales standards set. How do you know if a sales rep is performing well if you only have one? Two sales reps help you work out what is the standard for a high-performing sales rep, and what is average (or bad). Moreover, two sales reps mean you'll have twice the firepower, less dependence on individual performance, and of course, you'll benefit from friendly competition between them. 

Most importantly, if one of them quits, you still have half your sales team. 

The question of experience 

We're a house divided on this one. There are startups that swear by experienced sales reps and wouldn't consider hiring inexperienced candidates, and then there are those who much prefer fresh, green young 'uns who can be moulded. There is no one-size-fits-all solution here, and both approaches do work, which is why I've spun these off into their own posts. 

Whichever way you choose to go, remember that sales can never be hands-off for you. I've been lucky to be a part of several startups as a sales rep and sales engineer, and it never surprised any of us to see the founder(s) step into a product demo, or jump on sales calls with us. In fact, it often provided an extra push, knowing that the big bosses were watching and that this deal was of strategic importance. 

As the founder, everything you do matters. It sucks, but it's the job. You don't get to back off from difficult things, avoid difficult clients or behave in ways you don't want your employees to emulate. The great news is that this means you also have the power to set company culture. All those years that you dreamed of changing the workplace, the world? Yep, they prepared you for this. 

Now, go do it.