How to Get Into Sales — and Succeed

A healthcare professional, an international English teacher and an artist with military experience — what do they all have in common?

They all found their way into careers in tech sales.

Unlike for many professions, there’s no singular path into sales. Its blend of career growth potential and translatable skills make it an attractive option for both recent college graduates and working professionals eyeing a career change. Wondering what to do with that philosophy, psychology or English degree? Hop on the phone, and turn those communication skills into commission.

Excelling in sales, however, is another story. It takes more than the gift of gab or the ability to strike a gong (although more power to you, if that’s your jam) to rake in commission.

With the rise in sales technology, the profession has only become more competitive and data-driven. Hitting quota requires mastering email cadences, customer research and complex CRM systems. In some cases, a salesperson might have to play the parts of engineer, marketer and customer support on a call to explain the nuances of a complicated product to a customer.

But mastering those skills can lead to an array of job options, whether that’s as an account executive closing deals, an account manager working with existing customers or a sales enablement lead coaching others to success.

We spoke with three salespeople about the paths they took to get into sales, and how they’ve found success.

 

How did you get into sales?

I was working in healthcare and had applied to work for the Centers for Disease Control and Prevention, only to find out that they had discontinued the project I wanted to work on. Without that job, I didn’t want to be working in healthcare much longer. That was when my mentor brought up the idea of working in tech sales. I didn’t even know what the job involved, but after doing a little more digging, I became interested. I liked that there was an opportunity for growth, which was something I didn’t have in the healthcare field.

My first experience in sales came in 2016, when I was living in Shanghai, China. I was helping to run an English tutoring company with a group of other expats, and we had to get parents to invest in the company. The process was like raising a seed funding round. Then I moved back to the United States in 2017.

I wanted to get into tech, but I didn’t have any connections. Sometimes this job traffics in a space that minorities aren’t connected to. Most of my friends are lawyers, accountants or doctors. I’m educated, I have military experience, but I would never have traveled in the tech circle. That’s when I connected with SV Academy, which helped me get my foot in the door at my first company, Sisense.

I taught English at a university in South Korea for 10 years before moving back home to Chicago, where my skills weren’t as in-demand. So, I bought a car on Craigslist and started delivering groceries. I turned that into a mini business and went from delivering groceries to packages to doing paratransit. By the end of 2019, I just wasn’t seeing any real growth, so I started looking at other options. That’s when I came across re:Work, a nonprofit that specializes in helping people from disadvantaged communities like mine find opportunities in tech sales.

I’ve always had an interest in sales and had applied to sales jobs in the past, but I wasn’t even able to get an interview. So, I applied to re:Work and entered the sales training program in 2020. It’s an eight-week program, but I was able to get my first interview with a company in the third week and my first job offer by the fourth.

 

How do you approach explaining complex technology to customers on a sales call?

Whenever you’re on the phone, you should always understand what the customer’s goal is for the conversation and what you want from them. When you think of how to position your company, it’s helpful to know what they think about the product. If they think we’re an e-discovery tool and I’m trying to sell them the e-discovery solution, I don’t want to talk to them about our enterprise search function and confuse them. Conversely, if they don’t think we can do e-discovery and that’s what they want, then what I need to do is educate them. When you’re describing the product, try to keep it open-ended so that you don’t close off opportunities. 

My manager says it’s like going to the doctor. The doctor won’t just look at you and prescribe medicine, he asks you how you’re feeling, where the pain is, and what you are there to fix. It’s the same in sales. In order to solve a complex problem, we have to understand what the customer is even trying to solve and why they need to solve it. You need to start with a good discovery. I also like to ask customers what other solutions they have tried. Once you understand the issue, then you can prescribe the solution with your product. 

The first step is understanding the product yourself. I know it’s rudimentary, but for something like insurance, which is very complex, being able to understand it enough that you can explain it carefully takes time. I found listening to how other people explain it to be very helpful as well. Most of my customers have no background in insurance, so I try to keep it as simple as possible and use concrete examples.

 

Sales has increasingly become a data-driven and tech-assisted profession. What technical skills do you need to excel in this field?

If you’re in the marketing or business intelligence space, the ability to write even a little bit of SQL can be huge for leveraging analytics. But the most important thing is to commit to being an expert in the one tool that’s going to bring you the most success. If you start at a company as a BDR and they have Sales Loft or Outreach, immerse into the training videos and learn the tips and tricks to customize the system. At the highest level, most of those tools are similar. So if you can become an expert in it, you can bring that value to your next job. 

Understand how to use Salesforce, at least at a very high level. You’re going to use Salesforce or a similar CRM whether you end up as an SDR, an account executive or customer success manager. You can’t avoid it. The other thing is to understand how to use email cadences. Every company uses a different tool, but if you understand how to create an opportunity with email cadences, that’ll help you be successful. 

Learning email sequences and having a cadence of messages that you can set over the next seven days is huge. It keeps my name in front of them and makes sure that we stay top of mind throughout the sales process. It’s also important to spend time learning about your CRM, and how you can use it to make your job easier. We don’t have direct phone numbers, so I’ve learned to use the notes section to flag customers who are mine. I also live and die by setting follow-up tasks in our CRM, which helps me simultaneously take on more leads and manage existing ones.

 

What other skill do you find most valuable in your work?

Listening, more than anything, is what sets you apart from other salespeople. Are you quick to talk about your product, or are you listening to what the customer is saying? I always try to recap the conversation to make sure that I was fully listening. If I missed something because I was thinking about an exciting deal or solution, the recap creates an opportunity to circle back and make sure I have all the information I need.

If you’re a BDR or an AE doing outbound sales to generate your business, it’s important to have “soft eyes.” You need to be able to look at someone’s LinkedIn and see how their skills and resume all connect together for an opportunity. You need to be able to listen to them on a call and figure out what their problem is and how you can solve it. No one is ever going to tell you the exact things you need to check off your list to qualify as an opportunity, so you have to connect the dots on your own. Then you have to be able to paint a picture for them of how your product can solve it.

It’s important to understand that you’re going to be in this constant state of evolution, and being comfortable with that growth. In tech, it’s kind of a given that things are not going to be the same a year from now or even a month from now. As a salesperson, being able to take constructive criticism, incorporate that into your process and evolve is so important.

 

What strategies do you have for maintaining your sales pipeline and hitting quota?

It’s always a challenge to find that pipeline stability. My target is to take anywhere from nine to 12 leads a day, which keeps my pipeline full while also giving me enough time to help everyone else in my pipeline. Then I’ll look at my pipeline and see if there are any customers who I haven’t had any connection with for more than 30 days and mark them as lost. Marking my lost leads and maintaining a clean workflow keeps my head on straight and allows me to keep moving. I try to do that every week.

There’s more than one way to hit quota, but the three most successful ways I’ve seen are the dog method, the product expert strategy and leaning on what you know. The dog method is like, “I’m hitting quota even if I need to burn through 75 contacts before lunch and another 75 after lunch.” Then there’s the product expert strategy, where you understand the product so well it gives you immediate credibility. The third way, which is what I did, is to lean on what you know. Once you get a deal, reverse-engineer all the steps you took to get that deal and do that again. And lean into the messaging and process your team gives you to start.

If your quota is $300,000 for the quarter, you just have to make sure that every week you’re bringing in $25,000. So using an Excel doc or whatever you can to keep track of your pipeline each week helps. If you miss your goal, then you know you have to make up for it next week. Good reporting will also help, so you don’t have to go through all 100 reports every day. If you do miss your quota, understand that it’s normal early on and that it takes time to learn the software. Give yourself a grace period and learn from people who always hit quota.

Day in the LifeWhat Does a Customer Success Manager Do?

 

What advice would you have for someone interested in advancing in this profession?

I started at Intercom as a sales development rep, and then I moved on to be an account manager and then an account executive. What helped me find success was having a growth mindset and being able to adapt to change. You have to be up for the challenge. I was always ready to learn from every project that they gave. I always raised my hand to work collaboratively with product marketing and other teams outside of my role. If you have to go above and beyond your role, do it. That’s how you set yourself apart from others.

Lean into what you’re good at. I’m good at research, so I researched the hell out of these companies and who I was talking to so that the messaging felt targeted to that person. I did that at scale, so all I needed to do is call them when they opened the email. It’s also helpful to have a mentor. They don’t need to be someone who’s 25 years older than you, they just need to have more experience in the industry and are at a different company. I can bounce ideas off my mentor and get honest feedback that I might not get in the workplace. That ability to be transparent and have a sounding board is so valuable in this career.

I reached out to my HR manager and mentioned that I would like to have someone as a partner or mentor to help as we transitioned to working from home, and they set me up. It’s been so helpful to have a partner to answer my questions, listen to my calls and tell me how I can save time or relay the information more succinctly to the customer. There have been times during this journey where I’ve felt defeated, and my mentor has been able to give me some outside perspective, tell me that they’ve been through the same thing and offer some tweaks.

 

Like the rest of the tech industry, tech sales falls short when it comes to diversity. What advice would you offer to other members of underrepresented groups in navigating that?

When I first went to interview for Intercom, I did a tour and was so struck because I didn’t see one person who looked like me. The good thing was that they were open to making the team more diverse, and they ended up hiring more African Americans. I’d say, speak up if you’re noticing your team isn’t diverse, or ask why? There’s nothing wrong with asking what we can do to attract more individuals who look like us in the recruiting pipeline. The tech industry needs diversity. The other thing you can do is look for teams that are more diverse with whom you can share your experiences.

If you experience a microaggression or feel frustration, don’t be afraid to stand up for what you believe in and what it is you think hurts you. It will only be to your disadvantage if you don’t. You have to let it out in a professional way, whether that’s to your mentor or someone at the company so that you can get counsel on how to move forward with it. If you just carry it, then it’s going to fester and then you’re going to be perceived as the problem.

I spent 10 years of my adult life in a country where I looked different, spoke a different language and acted differently from the people around me, so it’s not uncomfortable for me to be in situations where I stand out. I was aware that I’m older than most people in this industry, that I’m female and I’m not the same color as other people working in this industry.

I would say what makes tech special is that there’s a progressive, forward-thinking way of doing things that transcends the product and gets into how we treat each other. Within my office, I’ve been pleasantly surprised at the effort and genuine care that has been put into diversity, unity and inclusion. Diversity and inclusion is a core pillar of our culture, and it’s not something special that we do only on Fridays or something like that.

Checking Back In7 Ways to Make Follow Up Emails More Effective