Wins and Losses of Working in Startup Sales Stability or promise of growth?

Everyone and their moms has a startup idea.

A handful of those people actually follow through on their ideas.

Out of the handful, an even smaller subset gets to launch their product. Some of them pick up clients along the way.

When they come to the point that they realize, “Hey, this could really be something,” they will want to hire a salesperson to grow their startup.

And this salesperson is literally a sales person. In startups, it’s usually THE only person dedicated to sales.

Do you see yourself doing this? Is working in a startup a good career path for you? Will it be a fulfilling move?

In this post, we examine the wins and losses of working in startup sales.

What is a startup?

I know the term startup has been and is sashayed oh so much, so for the purposes of this article, we take the definition from Warby Parker Co-Founder Neil Blumenthal, “A startup is a company working to solve a problem where the solution is not obvious and success is not guaranteed.”

Through market research and social listening, among other techniques, startup entrepreneurs identify and develop products that will “revolutionize” the way businesses operate. Startups roll out products that seek to solve pain points and reduce inefficiencies that were otherwise accepted as norm or haven’t been solvable in the past.

The fastest growing category in the startup world is SaaS or software-as-a-service where applications accessible through the internet are provided to clients through subscription. If there’s a good product-market fit, SaaS companies have huge potential to grow exponentially because there’s no need for outrageous manufacturing capital to scale.

With the boom of software, the world of business has been turned around and shaken.

At least one product has been developed for every niche that you can think of. Hotel management software like InnGrid addresses the hospitality niche. FreshTemp is another one addressing food safety in restaurants. Slack boomed last year as a team collaboration tool that’s now being used by you and me and huge megacorps like Apple and Microsoft. Hubspot,KissmetricsBuzzSumo and NinjaOutreach are just some in sales and marketing.

There are many, many, many, many failed startups. Lofty goals at month 1 to 6, and looking for a way out for the rest of the year.

But there are also a lot of startups that successfully transition into being a stable, profitable businesses.

And these companies bring their first employees along for the success ridealong. Not too shabby.

Well, that’s a quick overview.

We’ll dive deeper into the matter so sit tight.

Whether you’re a seasoned salesperson or looking to transition into sales, this post is for you.

Losses and Wins of Working in Startup Sales

If you’re looking into joining a startup in a sales role, you need to know that startups take a long time before deciding on adding new people into their core group. For most, the salesperson will be the first salaried role, their first employee. There is immediate expectation of pulling in sales. A large portion of the startup’s future will be reliant on their early stage sales operations.

This is in contrast to a corporate sales job where you enter a huge organization where the margin for error is somewhat wider.

For startups, mistakes can be very costly. The pressure to perform is intense— but it usually comes with a promising future. Where in corporate jobs you’re stuck in the same salary scale for a long time (we’re talking XX years for some!), the base pay in startups is probably very low to start (with a lot of OT!)—but the salary usually scales with the growth of the company.

Stability, adopting an existing method and being part of a huge sales machinery=corporate.

Adventure, creating new workflows and searching for new ways to sell, and being the bizdev, SDR and sales rep all at the same time=startup.

From the Founder’s Lens

Let’s look at things from the eyes of a startup founder.

Most startup founders—especially technical founders—are lost when it comes to putting together a sales team, hiring new members or even just hiring the first salesperson.

How much does the salesperson get? How is their work structured?

A startup does not have money to throw away.

Expect that the salary for the first or first few salespeople at a startup will have a low base, good sized commission percentage, some benefits and a pretty handsome on-target earnings/performance pay.

A base pay of  $25k is not unheard of. Your pay grows as you grow revenue with the startup.

There are also startups that can only afford to pay commissions. It’s not a very good set-up but it’s a reality for some founders.

For a startup, it only makes sense to hire and keep a salesperson if the total amount of the deals they close is more than the cost of their hiring. If there are not enough leads coming in for the founder before hiring a sales person, it might be hard to hit revenue goals. However, for founders with no prior sales experience, their first hire takes overall tasks within the sales process: from lead generation to closing and caring for the clients.

The Gamble of Startup Sales

Should you work in startup sales?

It depends on many, many factors.

If you’re a beginner in sales, it might not be a great idea to begin your sales career in a startup setup. Why? Well, more likely, there will be no one to guide your clueless self.

But that can only be positive. There are a lot of ways to learn. Everything is on the internet. The startup can sign you up with a mentorship program with an advisor or a more senior salesperson from the startup circuit. And, of course, you can learn from experience.

Learning through application is hands down the best way to acquire new skills.

When you’re salesperson #01, there is no document that will tell you what exactly it is that you do. Your focus is sales but you’ll probably work in product, marketing, lead generation and all areas that need work as the startup shoots for growth.


What does it take to work in startup sales?

Like I said, whether you’re a seasoned sales pro or a newbie in the game of selling, startup sales is a challenge.

Here are some things to remember if you want to succeed in a startup sales role:

1. Be an eager learner.

It doesn’t matter if you’ve been selling since Bill Clinton or you just got out of the womb yesterday. Mistakes? You’re going to make them. Be humble and learn. Startups and startup sales are a whole new animal—different from anything you’ve dealt with in the past.

Be a sponge and take in as much wisdom and experience as you can. In the world of startups, learning isn’t just about listening, reading and shadowing—it’s all about getting your hands dirty. There’s a world of difference between knowing about something and actually knowing it.

2. Only open your mouth when you have something worthwhile to say.

Okay, so hold off on the violent reactions. This doesn’t mean that you go mum and just shut up. Keeping a mindset of only speaking when you have something meaningful and helpful to say challenges you to think on your feet and skip the fluff—get to the meat and meaning right away. This goes a long way in sales. Prospects will know if you’re just buttering them up.

3. Don’t get hung up on selling. Help.

People don’t like being sold to. They will only put weight on what you say if you help them or give them something of value first. Especially for startups where you really don’t have years of track record to back you up. You need to prove your brand’s value by showing that you empathize with your prospects and you’re there to help.

4. Proactively build relationships.

One amazing thing about working in a startup is that even if it’s a small group, the company is part of a larger startup community. Begin from there. Network sincerely. Networking is not about distributing business cards. It’s about finding mutual connections, knowledge sharing and collaboration. It’s a great practice to share thoughts and experiences with salespeople from other startups in various stages of growth!

5. Learn to adapt quickly.

You might master the product quickly—but an update on the interface and features can happen anytime. You might be liking the territory you’re working on but change of plans may need you to focus on another area. You might transfer offices. You might even change founders and be retained. Such is life in startups. Be ready to adapt.

6. Know the value of your product.

Negotiation begins with knowing the cards you have. When doing sales for a startup, it pays to know that clients will want to get your product for a lower price—no matter how valuable it is. You’re in a startup desperate for a sale. And they know that.

However, the only way you can comfortably negotiate is if you know the value of your product: what it can do to improve the business of your clients, what pains it addresses and how it virtually pays for itself. Knowing the value of your product is valuable beyond presentation, it’s the core of your sales process.

7. Throw your assumptions out the door.

Fifteen years in sales? Know the buying behavior of enterprise companies in a certain industry like the pin of your phone? Well, throw those assumptions out the door.

You believe the best time to run a sales operation is 9 to 5? Well, times have changed. Cliche? Yes. True? Yes. Your clients are Googling you at 7am. They’re free to take a call at 7pm. Will you be there? Or will you think that it’s disrespectful? Worse, will you shrug it off and say, “that’s just not how things should be done.”

In a startup, you test, see what works, and run with it.

8. Be a people person.

It’s non-negotiable for a person in sales to be a people person. Basic: aim to please. However, when working with startups, you don’t have people coming to you at first. People don’t have assumptions about you that you’re a bigshot formal enterprise like Oracle and IBM. You’re a startup and a huge edge you have is that you maintain the human touch of software.

Sell your product through stories, through words that actually mean something to people other than a bunch of technical documentation that people rarely care about when it comes to first impressions. Be a person. Be a people person.

Is startup sales for you?

There are other factors to consider when choosing a career path in sales. Even within the startup circuit, the companies vary so much and the ways companies operate are diverse.

Do you want stability? Or the promise of growth? Are you about patented, proven techniques? Or do you like the concept of hacking processes to produce explosive results?

Let us know in the comments below!


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Aki Merced

Aki Merced

Aki Merced writes about B2B sales and marketing as a content marketer for Tenfold. Follow her on Twitter @akimerced!

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