Career Stories

“I Created a Chatbot For You”—How Gregory Williamson Won an Entry-Level Sales Role

Morgan Von Gunten
March 2020

Gregory Williamson is a Praxis participant who used Crash to pitch companies. His story stands out to me—he went above and beyond to win his Sales Development Representative role at Scripted, a startup providing written content for thousands of customers.

Instead of only sending a resume, he created a chatbot that solves a real problem for the company.

So I sat down with Gregory to hear his story, his advice for job-seekers looking to win a job without experience, and more.

Here are the highlights!

What’s the story of you winning your role at Scripted?

Before the interview, I went and looked at their website, looked at ways I could improve their platform (from a sales perspective primarily). And I noticed that they didn’t have a chatbot on their website.

They had Intercom, but they just had a little box for you to message them and nothing more. So for after-work hours and on the weekends, you couldn’t engage with people that were visiting the website.

So I thought, “Let me build out a chatbot for them.” I went and started a free trial of Intercom and created an entire Q&A branch, built out a script for them, and then I put it all into my Intercom account. 

Then I recorded a short video explaining what I’d done for them. I sent that over to the CEO before my interview with him, kind of as a value proposition slash pitch.

After about a week, they offered me the position. I credit a lot of that to the fact that I went and built that value proposition.

What questions did you ask the team in your interview to stand out?

I asked, “So what is your sales team’s biggest struggle or biggest pain point? I noticed that you had Zendesk before. Now you’ve just switched to Intercom. What has that transition been like?” And then I would go into, “What are your biggest successes so far? How many people are on your sales team currently?”

What was your process for approaching the job hunt?

Being in Praxis was a huge part of the process. I was always clear and to the point in email communication or any other type of communication, and I was very, very fast. I was also extremely targeted in my approach. I was primarily interested in sales slash customer success roles, as well as specifically B2B or Saas companies. So I targeted those companies only because I knew that that’s what I wanted. 

I created some pitches, too. When you’re creating pitches, you’re doing some extra work on the front end to help them make this connection to, “Hey, I’m a good fit,” not just handing them a piece of paper that says, these are bullet points about me, and I want you to see if I’m a good fit for you. I always kept that in mind. 

My project for Scripted was very similar to pitch, but it was just a little step further, a little more digging into it. Ultimately, I do think that that helped me land a job. I don’t know if I would have landed the job without that.

Did you have any work experience before doing this?

I have my own podcast on the side, and I worked at Chick-fil-A for three years. I was a manager there. But other than that, no. 

What would be your advice for someone who wants to get a job at a startup, but they have no experience?

Create experience.

You don’t have to wait for somebody to say, “Hey, this is your opportunity to learn and grow.” You can make that opportunity for yourself. 

I did this with a portfolio project—I went and looked at startups online. I found problems they had that were maybe recurring (they could have been way off the mark, but I just wanted to take the opportunity to learn more about calls and understand their pipeline and how I could improve that). And then I ended up creating a chatbot. That’s how I could solve their pain point. 

So allow your curiosity to take you somewhere and then create something from that. And then you can show what you make to people—you can use it as an experience. You could also use it as a talking point when you’re in an interview or something like that if they ask about experience.

But then just take that a step further.

Once you do find a specific job that you’re looking at, a job you’ve gained interest in, and maybe they gave interest back, take that time to use the skills that you’ve gained from previous experiences that you’ve created, and then make it specific to them and create value for them.

What made you make the switch from working as a manager at Chick-fil-A to working in sales?

Sales, ultimately, is helping people solve their problems and empowering them to build something bigger than themselves. That’s my life mantra—I just want to empower others to build something bigger than themselves. 

In Scripted’s case, when I get a client to sign on to use our writers, it helps them build their business because they don’t have to worry about writing. They can worry about building their business and doing what they do best. And on the other side, the Scripted platform powers freelance writers to grow their portfolio or make money and just do what they love. 

Ultimately, I want to grow my ability to sell because I want to start my own business one day and be able to pitch to investors and grow and pitch to customers or potential customers. And I think that is a great way to get started—to gain experience in sales.

After your job hunt with Praxis and Crash, what do you feel like you walked away with that you didn’t know before?

The confidence to land any job I want. All you have to do is make a connection, make it a valuable one, and that signal speaks so much louder than anything else.


Gregory is an entrepreneur, innovator, and someone who always strives to create value for others. Learn more about him on his personal website, listen to his podcast, or connect with him on LinkedIn.

If sales sounds right up your alley as you launch your career, check out this ultimate guide to getting started in a sales role without experience.

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