blog article

Why I Chose Software Sales over Software Development with preHIRED

Imogen Crispe

Written By Imogen Crispe

Last updated on October 21, 2020

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    Table of Contents

  • Q&A


After working for a religious nonprofit after college, Isaiah Ascher wanted to get into tech. He started learning to code, then a friend helped him get a customer services and sales job at an insurance company, where he thrived. But Isaiah wanted to go a step further and get into software sales, so he enrolled in preHIRED’s SaaS sales training program. Isaiah tells us about why he enjoyed the preHIRED curriculum, and how a previous preHIRED grad helped him land his job as a Sales Development Representative at!


Tell me about your background before you completed preHIRED’s SaaS sales program.

I had a rough childhood – I bounced between foster homes until I was adopted. I was forced to do things for myself, take care of my siblings, and make sure there was food in the fridge. It was difficult, but it’s made me incredibly driven to succeed.

I was never really looking to get into sales, I just sort of stumbled into it. After high school, I attended Bible college and then worked in digital media for a religious non-profit in San Francisco. I worked on their website, social media strategies, and helped implement new technologies so they could receive donations via credit card.

When I moved home to St. Louis, I used Codecademy and Code School to learn to code and try to get into software development, but it was limiting. There was no way to scale my income if I worked harder or smarter. Then a friend helped me get a customer services job at a call center for insurance company Carshield. Within the first month, I received a raise! After six months, I transferred to a sales role with a base salary plus commission. In my first week in the sales department, I surpassed their deal goal and I felt like it was something I could really do with my life.

Eventually, I was looking for more than consumer sales, so I decided to apply for a job at Square. At this point, an ad for preHIRED came up on my Facebook feed, so I did some research about their SaaS sales training program, and used their free tips to actively sell myself to Square as a salesperson. But I was second for the role, so I went back to preHIRED to learn more about software sales process.

Looking back, how have the skills you learned at Bible college and in web development helped you become a successful software salesperson?

Studying hermeneutics – trying to understand the original intention of a text through a language like Greek or Hebrew – in Bible college was helpful. In software sales, you’re really trying to find and understand the need at the prospect company. I never really correlated it until a couple of months ago. I also passed out tracts on the street which I never thought of as prospecting but it actually was! I would talk with people and collect contact information to follow up with them later – it was an entire sales sequence right there. I didn’t expect to see such a correlation between those life skills and my new career, but it’s exciting to find them.

Regarding web development, someone who is coding is someone who wants to understand how things work. I wanted to understand how a website is built. My adoptive dad is a software engineer, so while he worked on the backend, I would ask him how to make something look beautiful on the front end. From there, I started teaching myself coding languages like HTML, CSS, Python, Ruby on Rails, and more. I like to teach myself things. With software sales, you have to be willing to get things done, though you don’t have to teach yourself.

What was the preHIRED application and interview process like?

After applying on the preHIRED website and taking an assessment, I had an interview with a Growth Partner, Lael, who then spoke with Josh, the founder, and they agreed I could be invited into the program. They are very particular about who they accept, especially since they have a money-back guarantee – they want to make sure that everyone is successful, and that was very cool to me. They are really focused on making sure you’re going to be successful and get a job as soon as you can.

What was the preHIRED curriculum and learning experience like?

The online program is 40 hours long – a lot of people take about two to three weeks to finish (probably a bit longer if you have a job or kids), but I completed it in one week. There are videos and practicums, which can help you learn about platforms like LinkedIn and other specific sales tools. I loved technology so already having that background knowledge helped me significantly.

The program is broken up into modules – I focused on one at a time, went through all the videos, and then completed a practicum to demonstrate what I learned. As an example, after the LinkedIn Module, I had to show that I knew how to use the platform with a photo, a headline, and a flushed out profile, and then the program staff could check it to confirm I actually did the module.

The preHIRED staff check in with you every week to see how it’s going, where you’re at, and whether you’re submitting all the materials for the certification. They also have 1-on-1 mentoring where you can book video calls to practice the sales skills you’re learning and to prepare for interviews. We could also can contact preHIRED staff for assistance via email at any time, and they were very responsive. Because they teach you to use sales tools that notice how quickly someone opens your email, we can see how fast the support staff are opening our emails and responding. It’s pretty cool!

What topics were covered in the PreHIRED modules?

The cool thing about preHIRED is they use job hunting to teach you how to do the job of a Business Development Representative. So you’re doing the work of finding your job in the same way you’ll prospect for a new contract at your future software company. The curriculum focuses on three key categories for sales success: Tools, Skills, and Workflows.. The goal is to help you learn how to prospect, qualify, and connect with hiring managers or a VP of Sales, and how to build an impactful sales system so you’re not wasting your time writing emails over and over again. You learn how to have a meaningful conversation with someone you’ve never spoken with before – which is exactly what you have to do as a job applicant, and as a salesperson.

Because I’m a tech guy, I loved learning and using all the tools. I’ve used CRMs (customer relationship management tools) before, but I used a different CRM at each company and only had basic training. preHIRED covered six categories of sales software I had no idea even existed outside of just CRMs: CRMs, lead generation, lead enrichment, sales automation, productivity tools, and even artificial intelligence. They also teach you soft sales skills like handling rejection. These are basic skills that can benefit anyone entering sales at any point of their life.

Once you got through the learning material, how did the preHIRED team help you prepare for job interviews?

The preHIRED team went over interview questions with me, and I was able to come back with additional questions and scenarios. They help you with interviewing in general as well as specific questions that software companies will ask. Companies can ask some really crazy questions to see who you are as a person and how you’ll interact with the team, so it was good to have that preparation ahead of time.

Were you able to communicate with other preHIRED students during the program?

It’s not exactly a classroom setting, but you’re aware of the other students who are currently doing it or have gone through the program because they have a Slack group where everyone can interact. Alums of the program are interacting with current students, and that’s actually how I got my current job as a Sales Development Representative at

That’s awesome! Tell us more about how you landed your job at Outreach?

I read an interview on the Course Report blog with Philip Jansen, a Sales Development Representative at Outreach, and I reached out to him through LinkedIn to learn more.

I also listened to a podcast interview with Outreach’s Sales Manager. At the end, the interviewer asked how someone could get in touch if they were interested in working for her – she invited listeners to go to her LinkedIn profile and call her cell phone directly. So I did!

I had already applied to Outreach online and spoken with Philip, so using the preHIRED selling tools I had learned, I was able to have a very natural and friendly conversation with the Sales Manager. She loved the fact that I reached out directly and brought me straight to the final interview. Philip was able to advocate for me in the office and she was also familiar with Josh at preHIRED. She even asked me if there were other students she could hire!

What does Outreach do and what’s your role at a Sales Development Representative?

Outreach is a sales automation tool focused on helping sales teams sell more. They do this by helping sales members prioritize leads, stay informed on new events related to their leads, and stay on top of opportunities. It’s really exciting.

As a Sales Development Representative, I do outbound sales through prospecting, and I try to set up meetings so we can do product demos. Outbound sales is where the marketing department uses email technologies to send me the names of people to cold call or email who may never have reached out to the company, but may be exploring the website or are interested in the product. “Prospecting” means that I am actively going out and talking to people who are interested in getting the product or service.

Why did you decide not to go forward with being a software developer?

I’ve thought about it a lot, but at the end of the day, sales drives business. I just fell in love with sales. I love software sales because I first fell in love with software and how it works. But there are so many successful sales people who came from nothing and are now multimillionaires – I don’t care about having all that money, but I’m determined to create something from nothing and I love going up against the challenge of someone telling me “No, this isn’t going to work.”

What advice do you have for people thinking about making an intensive career change through a program like preHIRED?

Just do it. I understand there are so many things, like family, that can hold you back, but I don’t think about that. I asked myself, “What can I do that’s going to help my family and put me in a financially stable position in 10 or 20 years when my kids are ready to go to college?” That’s why I did preHIRED.

Sometimes, we think we can’t ask for help when we’re teaching ourselves something, but it’s ok to ask for help. Compared to before preHIRED, my base salary is much more and my on-target earnings are going to be much higher. I might have eventually figured things out on my own, but there was so much I didn’t understand. I learned much more quickly through a program with someone teaching me. It wasn’t easy at all and was definitely a challenge, but once you’re done and working, you’ll be much happier.

Find out more and read preHIRED reviews on Course Report. Check out the preHIRED website.

About The Author

Imogen Crispe

Imogen Crispe

Imogen is a writer and content producer who loves exploring technology and education in her work. Her strong background in journalism, writing for newspapers and news websites, makes her a contributor with professionalism and integrity.

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