7 Career-Defining Lessons I’ve Learned Throughout My 3 Years at a High-Growth Startup

As a Solutions Consultant at Outreach.io, I’ve seen the SaaS company grow from less than 50 people in January 2016 to about 300 people today!

Our expansion has been so prolific that it’s safe to say that Outreach.io is, in fact, one of the fastest growing SaaS companies of all time. That isn’t to say it’s been easy—there have been times when I’ve felt completely defeated only to come back to work the next day and feel defeated again. However, there’ve been other times where I felt like climbing to the highest mountain and letting out a victorious war cry. Such is startup life.

During my tenure at Outreach.io, I’ve managed a Technical Support Engineering team and have provided a vast array of businesses with effective sales strategies as a Solutions Consultant.

Needless to say, during my tenure, I’ve learned plenty of valuable lessons. In some cases, it’s been a school of hard knocks but most of the time it’s been an entirely fulfilling, enjoyable experience I wouldn’t trade for anything.

In reading on, I’ll delve deeper into some of the more poignant lessons I’ve been taught throughout my time at a fast-paced SaaS business!

1. Be Prepared to Wear Every Hat Imaginable

If you intend on contributing to a successful SaaS company, you’re going to need to check your job title at the door.

For instance, just because my role dictates I manage the Technical Support Engineering team doesn’t mean I simply stay in that lane.

As as early employee at Outreach.io, I’ve had the opportunity to wear dozens of hats.

We started with less than 50 people, so all of us (myself included) have had to step outside of our comfort zones and perform tasks that didn’t necessarily fall in line with our title.

It’s easy to say “I didn’t go to school to do ______________ so I’m not going to do it,” but that’s how many other SaaS companies stumble out of the starting gate. If you’re a tech-wizard, you may have to put on a marketing hat once in a while. If you’re a marketing expert, you may have to put on the sales hat. If you’re the CEO, you may have to grab a broom and start sweeping floors. You have to do whatever it takes for the greater good.

Having a hard time coming to terms with this? Many successful SaaS founders work for little to no income when they are getting started. Let that be a lesson to not get stuck on your title—even if it means getting your hands a little too dirty for your liking.

2. Get to Truly Know Your Team

In continuing the theme of not getting stuck on titles, I’ve learned to never underestimate people.

Someone may have an independent contributor title but that doesn’t mean they don’t possess incredible leadership skills. As a manager, I’ve always been curious about the people on my team so I can learn how to tap into their potential, no matter their rank or tenure.

3. Don’t Sweat Your Competitors, Focus On Customers

One of the worst things you can do is try to price out your competitor. If you have similar software but you offer a huge discount to lure a client from the competition, what does that really say about your product? That it may provide less value. You get what you pay for.

In my time at Outreach.io, our focus has always been on building a better product to meet the needs of the customer. With a better product, you’ll be servicing your customer far better than your competitors. All metrics, such as activation and retention, should be based on customer experience. Then you won’t have to undercut your own prices to lure a client from the competition.

It’s also important to note that customers don’t care about your sales goals and company creed. They care about their own circumstances.

4. Understand your customers. Be Prepared to change with them.

As an add-on to the above section, you need to always work towards satisfying your customers and clients. Over time, their needs are going to change. If you intend on keeping them happy and maintaining a relationship that fortifies your business, you need to evolve along with your clients and learn to love it.

5. Learning at Lightning Speeds

At the onset of your SaaS company, you’ll start behind the 8-ball. You won’t have much in the way of customers, money, brand trust, or experience.

In order to catch up, you’re going to have to learn faster than anyone else. There’s a misconception that failing fast is a rite of passage of SaaS companies. That’s only true if you’re intent on falling short. The only way you’ll succeed in this industry is if you stop prophesized failure and start learning to succeed.

In saying that, prepare to be wrong a lot of the time. Your SaaS is a new business and there’s nothing set in stone. Just because you are wrong, doesn’t mean you’ve failed. It just means you’ve learned an important lesson. As Seth Godin states, "The cost of being wrong is less than the cost of doing nothing".

6. Stop Selling. Start Helping.

A great sales pitch is good for the short term. But selling is only good for today. Being a subject-matter expert is what gains lifelong clients that provide a foundation for your SaaS.

Google’s Zero Moment of Truth study revealed that most customers use around 10 sources of information before making a purchase decision. It’s crucial to focus your ‘selling’ on solving problems for your customers. By focusing on the customer relationship as opposed to the transaction, you’ll add value through the interaction, helping you stand out from the pack.

7. Happy Employees Garner the Best Results

We achieved a very aggressive revenue goal (a number we never thought possible) by December 2016. We rewarded our hardworking team with a trip to Cabo San Lucas. Therefore, I’m comfortable in saying company culture means the world to us.

You can talk about a positive company culture until the cows come home—but if your employees’ attitudes tell a different story, then your words will ring hollow.

Realistically, the way employees act dictates the culture of your SaaS. If you treat them the right way, they’ll be motivated to put their best foot forward and you’ll see the results you want. If you don’t, there will be a high turnover rate which can spell death for your business.

It’s not always going to be paradise, but transparency, honesty, and accountability make the tough times an accepted part of work life, and far more palatable.

Go get em’

Thinking about starting or joining an SaaS company yourself? These lessons should give you that extra nudge towards becoming part of an exhilarating and rewarding industry.

In fact, I plan on starting my own SaaS business in the next few years. From my experiences, I’ve learned without question that cultivating an amazing work environment for my people is the first step to success!