Podcast: What Working in Tech Startup Sales Taught Me About Entrepreneurship

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I got my start in corporate America in sales. It totally wasn’t planned, but after searching for a permanent full time job for about a year and a half after finishing college, it was my only option. I got into a corporate sales training program and the rest is history.

Looking back on it, though I complained about it a lot…I experienced biased, subjective treatment, strategies that didn’t make sense…like calling wrong numbers all day (YES, that REALLY happened), and dealing with both sales and customer service issues in the same job…I’m now seeing that I gained a lot of valuable skills—despite all that.

In the first few companies, I really only learned about how to speak well and how to deliver good presentations, but in my tech startup sales job, the one I left to focus on my business, I learned the absolute most there.

It was sort of an established startup, because they’d been around for about 15 years or so, but they operated like a new startup. There were lots of leadership changes and changes that affected our jobs. And our quotas increased every month to keep up with their ambitious company goals. I’d never experienced that in any of my other sales jobs. And that was just the internal stuff…of course we were on the phones constantly working through various customer scenarios all day and we’d get some characters on the phone, I tell you! People sometimes tell you their life stories, about their divorces, their kids, whatever. But it was definitely entertaining to say the least.

By interacting with people in that way every day, I started noticing certain patterns and behaviors that some people exhibited more than others. People who were usually going to buy acted one way, while those who weren’t serious, who we’d probably never hear from again, acted another way.

Now that I’m working on my business full time, I’m noticing how a lot of those sales fundamentals have also carried over into entrepreneurship. So let’s dive into them!

1. Have a mindset of unlimited abundance of clients and customers.

In sales it’s easy to get competitive with your teammates. Some days, you’ll see that your teammates get a ton of sales, while you don’t get anything. But I trained my mindset to view that as proof that I could do it, too. I had to remind myself that there’s an abundance of sales leads and opportunities for me to hit my quota, too. And just because one person got several sales that day, it doesn’t take away from me.

It’s the same in entrepreneurship. Sometimes, you can look at others in your industry and see them getting a ton of clients and think it’s taking away from you, but it’s not. To me, it’s proof that I’m in an thriving industry and I know there are plenty of people out who I’ll be able to help.

2. Have confidence when talking about pricing and benefits.

In sales, you have to be confident when talking about the pricing of what you’re offering. In my sales job, we were able to offer discounts, when people were really really interested, but budget was a problem for them. However, many of us (myself included) would jump to discounting too quickly, when we really didn’t have to. Those who were willing to invest were the best ones to work with and were the most eager to start implementing the software.

Oftentimes, when you articulate benefits really well and you show how the software will help the customers, discounting won’t be necessary. They’ll be ready to sign up and pay. Plus they will value what they’re getting more because they’ve invested more in it. They’ll have some “skin in the game.” For many of the customers who we gave deep discounts to, they’d put in cancellation requests to cancel their software subscriptions shortly after buying because they weren’t invested and they didn’t understand how the software was adding value for them.

The same goes with entrepreneurship. When you know your value and you communicate that with others, along with how they’ll benefit, they’ll be more likely to want to invest in you. People who are just price shopping usually aren’t that serious and they may end up backing out because they’re not even invested in working with you. Know your value and don’t be afraid to state it. It’ll help you attract the best clients!

3. Keep packages/offers simple and make it easy to buy.

In software sales, it’s easy to complicate things with all the features available for the software. However, people don’t need to know EVERYTHING the software does. They just need to know what will be useful for them and their specific businesses. When people feel overwhelmed with options, they’ll oftentimes back out because they’ll think they need time to think about it. And in sales, when people say that, it usually means the sale is lost.

I kept offers simple on the phone, only giving 2 or maybe 3 options that were a good fit for them and I explained how easy the buying process was. You can also compare this to restaurant menus. Think about the Cheesecake Factory menu versus a specialized cafe menu. The Cheesecake Factory menu has like 100 dishes to choose from so you could be flipping through it for like 20 minutes before you know what you want. With a specialized cafe menu with about 10 options, you’ll choose much quicker and easier.

This is why on my website, I only have 2 packages and the website audit. That’s it. I want it simple and straightforward and easy to understand so people can easily tell what their options are if they decide to work with me. This makes for a much better buying experience.

4. Follow up until people are ready to buy.

In sales, we did a ton of follow up. Yes, some people would disappear indefinitely to never answer any of our emails or phone calls again. But some just weren’t ready to buy when we first spoke to them, so we continued to follow up and they’d be ready a month or two later. I used to get sales all the time that way.

I noticed recently when I was looking for a photographer for my brand shoot, I emailed 6 or 7 photographers. While the one I chose, and who was my first choice, responded to me within a couple of hours, the rest who didn’t hear back from me could’ve followed up to see if I still needed someone or if I’d need another photographer in the future, but none of them did.

In entrepreneurship, you definitely want to follow up with any inquiries that don’t sign up right away because you never know who may change their mind. You could literally be leaving money on the table by not doing it.

5. Structure your client consultations.

In sales, I prepared before the start of any sales consultations. I would plan the agenda of what we’d cover, what questions I’d ask and how I’d articulate the benefits. This would help the calls flow smoothly and the customers would clearly understand where the conversation was going.

Having this experience has helped me plan my consultations in advance for web design consults to make sure I’m setting the agenda upfront, asking the right questions to get to know their businesses and to understand what problems they’re experiencing to make them want a a web designer, in the first place. By doing this, I’m able to explain how my services will help resolve those problems and how I can benefit them. I then end with a summary of the web design process and how they can easily get started. You want to make the getting started part as clear and easy as possible!

6. Leave a good first impression during consultations, follow up when you say you will, and deliver on the promises you made.

When I was in sales, I was always sure to give tips that the customer could use, regardless of if they buy or not so I could make a memorable impression. I’d offer marketing tips or maybe offer to send a helpful article they’d benefit from. And whenever, I’d say I was sending something, I followed through to build trust. People are deciding whether or not they want to buy based on your actions and how much they trust you.

And once they did buy, we, as salespeople, would’ve usually made all these great promises about the help they’d get with implementing the software once they came on board, so they would be eager to get started with our implementation team. However, occasionally we’d receive the calls we hated…a complaint that someone in implementation dropped the ball and it didn’t live up to the hype. There wasn’t much I could do about it then, since they were a totally separate department from sales.

But this is why, in my business, I have a process in place to live up to and exceed expectations. I also follow through when I say I will and I give a great impression on my consultations. I don’t want anyone complaining about my services or my turnaround time or lack of responsiveness.

7. Ask for referrals.

In sales, you can get closer to reaching quota from referrals, instead of only relying on new leads. For some reason, not a lot of people on my team asked for referrals, but I sure did! I used to tell every new customer I got about the referral program and I got a decent amount of sales from it.

Like I said in the above point, I’d also do my best to make a wonderful impression during consultations, so the customers would come back to me if they needed anything else, too. Sometimes we’d get people who wanted to add extra accounts or features, and those things can count for your quota a bit, if they contact you directly and you add it for them. Customers also had the option of calling into an 800 number to do those things, which would’ve sent them to another rep. But because of how I worked, I usually had my customers contacting me directly.

As a business owner, I’m sure to do a great job on each project, especially because I know people are happy to send referrals when you do well. And whenever they need something else related to what I offer, I want them coming back to me, instead of someone else in my industry.

8. Have good work ethic and perseverance.

Some days in sales, you make make like 80 calls and you get no one on the phone or you may only get people who aren’t a fit or who don’t have the budget. Those days are frustrating for sure! But you can’t stop. Your quota is still there and you still have accounts that need to come in from somewhere. You have to come back the next day and think of it as a clean slate and usually it gets better and you get your momentum back.

It can be like that with entrepreneurship, too. Sometimes you’ll put your content out there and hear crickets or maybe you don’t get the engagement you want on Instagram or you may get unsubscribers when you send an email. But who cares?? That’s a part of the game. People with 100,000 followers and a super engaged audience didn’t get it after being an entrepreneur for a month. You have to stay consistent and keep marketing and promoting yourself and your perfect customers/clients will come!

9. Have faith!

There’s a TON of uncertainty when working in sales. You never know where your sales are coming from, sometimes. And it all requires faith just to make it. Sometimes the end of the month would come and I’d still need like 8 new sales to make it to quota, but I’d usually get the sales I needed before the day ended. I once got 8 in a day. And everyone was wondering how I did it. But I woke up that day telling myself I’d get 8 to hit quota, setting that intention, and I’d make my huge cup of coffee and I’d come to work and get busy. And before I knew it, it was the end of the day and the sales I needed were there!

Your faith has to be bigger than your fear and doubt in both sales and entrepreneurship! There’s a lot of uncertainty in entrepreneurship and sometimes you don’t know where your clients will come from. You just have to know they’re coming…from somewhere. Know that as long as you’re putting yourself out there and delivering high quality work, you will be fine!

10. Have systems in place to stay organized and on track.

In sales, I had to use several systems like a CRM (customer relationship management) tool to organize customer info and notes, a calendar for sending calendar invites, a screen sharing tool to do consultations and demos, etc. Sometimes I’d also used canned email responses to respond to repetitive email messages.

I’ve been doing the same in my business. I took a course specifically for web designers called Organize & Automate by Nesha Woolery. It was EXCELLENT. It helped me get a CRM, canned emails, a project management tool, a calendar tool to allow people to schedule appointments with me (instead of going back and forth in email), and more! It’s saved me sooo much time and makes my process look 10x more professional and efficient. It actually makes web design more fun!

Whatever your business is, be sure to put the systems in place to help make your job easier and to give your customers a great experience.

That’s it! My time in sales wasn’t all bad, now that I’m looking back on it. I now see how it’s helping me in what I’m doing now. That’s how the universe works, right?

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