From Door-to-Door Sales to Director of Sales After Careerist

When Isaac Lewin enrolled in Careerist’s Tech Sales Bootcamp, he already had a solid foundation in sales. But Isaac wanted more than experience — he wanted credibility and a better understanding of tech sales. Isaac saw Careerist as a way to level up, gain industry-respected training, and position himself for higher-impact roles. Two years after completing the bootcamp, we caught up with Isaac to learn how the bootcamp has shaped his career. Today, as Director of Sales & Business Development at Country Life Natural Foods, Isaac is putting his Careerist skills to work and already seeing a significant return on his investment!

What were your career goals when you enrolled at Careerist in 2023?

I went to college for theology, and while there, I started doing door-to-door sales to pay tuition. I had never made so much money in such a short amount of time in my life! I was so interested in sales that I continued selling door-to-door. I found my way into doing tech sales at Web.com in Charlotte, North Carolina, which gave me firsthand experience with a marketing agency. 

I enrolled at Careerist because I wanted bigger companies to view me as credible. Careerist was more expensive than other tech sales bootcamps, but I figured they were asking that much because they believe in their bootcamp and that companies respect them. If I had a certification from Careerist, then I was sure that companies would take me seriously and understand that I had invested in myself. 

Did you receive any financing to make the bootcamp tuition more affordable?

When I enrolled at Careerist, my financial situation was not the best. I wasn’t working a full-time job, and I was looking at Careerist as a way to level up my career. Since I could not pay the full tuition upfront, my recruiter helped me get onto a payment plan with Careerist. The payment plan allowed me to begin the bootcamp right away while making tuition more manageable.

What did you learn in the Tech Sales Bootcamp at Careerist?

Value engineering is one of the big things that I learned at Careerist. As a sales engineer, you must be able to portray the value of a product, such as software, to a customer. Sometimes the value may not be immediately apparent, so you have to dig in and put yourself in that customer's shoes to understand the value. For example, at my current company, Country Life Plus, I just created a subscription service for our customers, which is like our own version of Amazon Prime. I took what we already had and reformatted it for this subscription model, so now there's a premium version of shopping on our website. 

We also learned about the consultative selling process and storytelling, which in sales, is story-selling. We learned how to communicate with the client, so they saw themselves using the software. These were some things I learned at Careerist that I had not gotten access to anywhere else. At Careerist, you have actual sales engineers teaching you how they sell. You’re going through the same process they use every day on the job. 

We also covered the basics of computer programming, like how all the different parts work together. As a kid, I built my own PCs and put things together, and my dad is a programmer, but Careerist helped me understand how everything comes together in a computer. It’s a good overview from the beginning of computing to where we are today. While at Careerist, I also took a short Python course, which gave me more programmatic skills, increasing my value. I'm not a coder, but knowing some code makes my life easier at work.

What’s the difference between tech sales and straight-line sales?

At Web.com, I learned the Jordan Belfort method of sales, also known as straight-line selling, which involves high pressure and emotions. To incentivize your selling, the company gave out little plush toys to showcase on your desk. For example, if you hit a certain number of sales or a type of sale, you would be given a whale or an eagle. After I made a big sale on a cold call, I got the highest award which was the eagle. My time at Web.com meant I was cold-calling people from all different types of businesses, like plumbers, roofers, lawyers, and electricians. 

Straight-line sales is totally different from tech sales where you’re more like a consultant building a relationship with a client. In a consultant situation, you're not emotionally pressuring people because you don't want the client to make bad decisions. These are clients who will eventually be buying thousands of dollars of a product, so you need to nurture that relationship and take the time to understand the company. Tech sales will also have some technical aspects to it, where you’ll need some technical aptitude in order to communicate, but you won't be a full-blown programmer. 

What were the instructors like at Careerist?

Careerist hires real sales engineers that still work in the field to teach the bootcamp. They bring so much value to the bootcamp and work at a high caliber – some of our instructors were six- figure earners in their day jobs! Their approach to teaching was treating us like we were upcoming sales engineers, not just students. 

Careerist has student success managers who support you outside of class. Everyone is assigned a student success manager, and they check in on you to make sure you’re on track with your assignments. They’re also there to help you with anything else, like your LinkedIn profile and resume. I’m still connected with my student success manager on LinkedIn!

What is the overall teaching style like? 

It’s a mix of live lectures and assignments. Different instructors joined our classroom time to give lectures. This was cool because we got to hear a diverse range of experiences in tech sales. Then we had coursework to do outside of class. 

Careerist also offers internships for its students! What was your internship experience like?

I began working again in sales while completing the bootcamp, so I didn’t have as much time to dedicate to my internship at Careerist. During my internship at Careerist, I took inbound calls and there were a few times when Careerist sent me leads to follow up. I talked to people, explained the value of Careerist, and let them know more about the program. 

What did career services at Careerist look like?

The LinkedIn optimization and the resume builder through Careerist were game changers. Most resumes are processed through AI before a human recruiter looks at them, and Careerist helped get me into the mindset of how to write for that. They also have a job application tool where you input your resume and it automatically applies to different jobs for you. It’s really powerful. We did mock interviews at Careerist, too. We did them in class while presenting demos to our sales engineer instructors. 

What was the first tech sales job that you landed after Careerist?

After Careerist, I landed a job as a Product Development Manager at a publishing company. Essentially, I was an advisor to authors interested in publishing, which is like an inbound closer. I would explain our publishing process and the value of it. After that, I got a job at a MedSpa as a Marketing & Sales Coordinator, and ran Facebook ads to get people to come to the med spa. 

What are your responsibilities as the Director of Sales & Business Development at Country Life Natural Foods?

Country Life Natural Foods has been around since 1960, and we specialize in selling non-GMO and organic products in bulk. It’s a small business and it’s scrappy. Since I joined, I’ve built their website on Shopify and worked on video content for the website. I'm even doing front-end manipulation on the website because I know some code. I run Facebook ads and marketing automation, and I am cold-calling businesses like dog bakeries to build our relationships. I’m attending events to direct-sell to customers who come to our table. Instead of getting paid hourly, I have equity in the company. When most people are clocking out to go home, I’m still around wondering what more I can do to make this business grow. 

Overall, have employers been interested in your Careerist experience?

Employers have not directly asked about Careerist, but because of my Careerist experience, I'm confident in interviews and can land jobs. 

Are you still using what you learned at Careerist now on the job?

Absolutely! I use what I learned at Careerist on the job at Country Life Natural Foods. I’m also upskilling. I just enrolled in a coding course so I can learn JavaScript.

What is your advice to people interested in getting into tech sales through a program like Careerist? 

No matter what the economy looks like, businesses are always going to need to grow, which means businesses are always going to need salespeople. If you’re going into tech sales right now, you have to be available and coachable. Sales jobs are great because if you have the right sales job, you can really make an infinite amount of money, as long as you're willing to work. 

At this point in your career, was Careerist worth it for you? 

It’s totally worth it. At this point in my career, I've made thirty times more than what I paid for the program. 

Find out more and read Careerist reviews on Course Report. This article was produced by the Course Report team in partnership with Careerist.