Tech Sales Bootcamp
Isaiah Payton
Before Springboard:
Independent business owner at Amway
After Springboard:
Sales development rep at OnBoard
“Everything I learned at Springboard is relevant to the job I do today. Springboard gives you so much valuable information and industry knowledge that’s not taught in school.”
“Everything I learned at Springboard is relevant to the job I do today. Springboard gives you so much valuable information and industry knowledge that’s not taught in school.”
Meet Isaiah Payton, a graduate of Springboard’s Tech Sales Bootcamp.

After nearly a decade in sales, Isaiah Payton has sold everything from freight to consumer electronics and household cleaning products. He gained invaluable customer service experience working in retail and at call centers. When he was laid off from his job as assistant manager at Johnston & Murphy in January, he enrolled in Springboard’s Tech Sales Bootcamp to learn about software sales.

He is now a sales development representative at OnBoard, a board intelligence platform, where he books discovery calls with prospective clients.

You’ve been in sales for over a decade. What made you decide to transition to tech sales?

Honestly, I’ve always been interested in the tech industry. Software is a more complex sale than retail. I’m always trying to challenge and better myself, so it seemed like a natural transition. I also like the laid-back culture at tech companies and being able to work remotely. I found the Springboard bootcamp and here I am today.

What is the main difference between traditional sales and software sales?

Traditional sales are typically a one-and-done deal. It’s more transactional. Whereas with tech sales, you have to do research for a specific client. You have to do prospecting and lead qualifying. When you work at a retail store, your performance is measured by how many sales you get, whereas with tech, the KPIs are more complex. It’s about attention to detail.

There are industry standards for sending emails, making a follow-up phone call, and which customer personas to reach out to

Did you feel prepared to start your first job when you graduated from Springboard?

I had a lot of confidence because I had learned all the skills I needed at Springboard. The hard part was learning to convey how my past experience in logistics prepared me for an SDR role. My career coach helped a lot.

How would you describe your job search strategy?

When I was applying for jobs, I realized I was going up against experienced sales development reps and account executives. The market is flooded with laid-off candidates who are now in the job market searching for the same position.

I had to understand the job market very carefully and target my job search. Initially, I was applying to big companies like Salesforce. I even made it to the final round, but they went with a more experienced candidate. Then I started searching for smaller companies. The hardest part was finding the right entry-level roles, knowing I was competing with more experienced SDRs.

The mass layoffs in Big Tech this year were very concerning. What advice do you have for other Springboard students?

Having confidence is a big thing. Don’t have impostor syndrome. Don’t think you’re not meant to be here. If a recruiter contacts you, they did it for a reason. As I said, I downloaded all the course materials from Springboard and reviewed them again, and that helped me build my confidence.

What was the best advice you received from your career coach?

Stay consistent, be confident, and keep networking. Networking played a huge part in my success. I had references and I met people in the same field who were potential future teammates.

Springboard requires students to do a certain number of informational interviews per week while interviewing. Did that approach benefit you?

It benefited me because it relates directly to the sales job. SDRs have to do a lot of outreach. Networking gives you the confidence to contact new people every day. To get 20 sales appointments in one week, you have to make 50 calls a day. Technically, those are informational interviews, where I’m probing to see if they need our product.

What practical experience did you get during the Tech Sales Bootcamp?

Everything from writing emails to making unscheduled calls. I took those scripts and adapted them to my job and our specific products. We did mock interviews and roleplays, which definitely translated to most SDR and BDR roles. I’ve used a lot of the communication principles I learned at Springboard in the emails I send on a daily basis.

Do you have any experience using AI in your work?

I used ChatGPT when I started my job to help me gain product knowledge. I went through all the case studies on the company website and fed this information into ChatGPT. Then I asked it questions. For example, I would ask, “What is the most common board management goal in higher education?” It would give me a summary based on the information I had fed it.

Sales reps have to create a lot of content, from responding to emails to doing cold outreach on LinkedIn. Do you think you’ll use generative AI for that?

I’m not sure. I’m big on personalization and I don’t want to get caught using AI, because some people are good at detecting it. But I might use it at some point if I need to summarize a report instead of reading the entire thing.

Tell me about your new SDR role at OnBoard.

We usually start with a morning meeting where we convene for 10 or 15 minutes. After that, we spend the rest of the day doing outreach and trying to book discovery calls. I dictate my own schedule. I have a lot of flexibility to do what I want, which is nice. The company gives me the freedom to experiment with different communication methods. I have a lot of freedom, but with great freedom comes great responsibility. I'm glad I made the transition.

How has your life changed since switching careers?

I’m in a new stage of my life. It’s a new challenge. And I love working from home. It’s nice to have more freedom than usual and not have to clock in. I feel like this opportunity will enable me to accomplish other life goals. For example, I’ve been wanting to move out of state. This job allows me to do that. I can also have a life outside of work, which is very important to me.

What was the most valuable part of your Springboard experience?

My instructor, Chris, was great. He explained everything so well and he made learning fun. The classes kept me engaged and the assessments were challenging and very relevant.

My career coach, Jan, helped me stay motivated. Having someone in your corner who also keeps it real with you helps you push through the hard times. I would vouch for Springboard any time of day just because I don't think I would have landed this job without it.

Some people are intimidated by the thought of doing cold outreach, so they never pursue a career in sales. What advice would you give them?

The worst thing that can happen is someone says no. Or they don’t respond at all. People psych themselves out when they’re making a call because they’re afraid of sounding stupid. Or they don’t like being told no or getting hung up on. I had to get over myself. It’s not a big deal. You will probably never talk to this person or see them again, so what’s the worst thing that can happen?

Once you get a sale, it clears up all your worries because then you realize you can do it again. You just have to find a method to the madness and be consistent.

Anything else you’d like to add?

I highly recommend downloading all the information Springboard gives you so you can review it whenever you want. I guarantee it will help you get a job, as long as you stay consistent.

Listen to your career coach. Pay attention during the live classes. Talk to your classmates and network. And remember that you probably already have someone in your network who can help you.

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