Case studies

From phone sales to six figures: How ACG helped Winston Smith

August 30, 2022

Winston Smith’s story is a testament to the real-life benefits upskilling can bring. In a very short time, Winston transitioned from phone sales to a thriving cloud career. He currently works full-time as a cloud architect, does contract work, and manages his own eCommerce brand. 

Driven by a need to provide financial stability for himself and his family, Winston worked tirelessly to build a basic knowledge of cloud from scratch. Incredibly, he accomplished the shift to a technical career with almost no professional influences, coming from a low-income community where his role models commonly worked “manual labor jobs with very limited career trajectory.” Now, Winston is a role model for his family and community, serving as a beacon of hope and possibility for career success. 

A Cloud Guru helped him get there, with hands-on learning opportunities that boosted his knowledge and helped him make a radical pivot to career success.

From phone sales to cloud architecture

Growing up, Winston found himself questioning the traditional approaches to education and work that the adults in his life espoused: "You go to school, you 'get your education', and you get into the workforce. I was surrounded by people working tirelessly, in dead-end jobs just to pay their bills and continue working in the same job day after day. I knew I wanted more than that. I wanted to thrive. Traditional education just didn't give me the same practicality and flexibility I needed to learn at my own pace.” 

When Winston did enter the workforce, as an insurance salesman, it proved less than ideal. He wanted a better salary, and he didn’t think his potential was being fulfilled: “As I entered the workforce in sales, I continually looked for ways to set myself up for success in non-traditional learning paths. Even as my career evolved away from sales and into retail, I knew there had to be options that would provide a brighter future for me and my family." 

So Winston made an agreement with his brother (who also worked in sales): They would both try to make a shift to a different industry. The only question was which one. 

“We did our research,” Winston recalls, “and there was an article on LinkedIn that listed the top 10 most desired skills. Number one was cloud computing.”

That settled it. Winston dove right into the cloud—and it didn’t take long for him to develop a genuine passion for it. Within 14 months of setting out on his career shift, Winston earned his first cloud certification. It took a ton of hard work to get there, and he threw himself right in: “I was practicing building AWS every single day. And when you're not technical, it can get very stressful and very frustrating because you’re learning something completely out of your comfort zone.” But in the end, the risk paid off, and Winston had his first major cloud achievement under his belt.

Where to go from there was another question. There was a lot to consider: “After you pass a certification, you have to learn what type of job you want to get. What are their requirements? Who do you have to speak to? You have to learn how to do technical interviews. I learned none of this.” It became clear to Winston that he wasn’t quite ready for a full-time cloud role yet. He needed to bolster his experience a bit more.

The goal of financial security kept him going through the uncertainty and the challenges:

“As hard as cloud was to get into, being broke is harder. I wanted to get into something that I could actually sustain. You know, I wanted to get myself a decent house, get a decent car, most of the bills tied up, those kinds of things.”

Although he couldn’t enter the cloud workforce yet, Winston did have the option to boost his skills further. He tried a wide range of learning providers before landing on ACG. For him, there was no comparison: “A Cloud Guru was significantly better than any other provider—the level of teaching, the level of care. And it just keeps getting better and better.” ACG’s courses were the most important aspect of the platform for Winston. His standouts include all the AWS admin certifications he took, the GCP associate engineer course, and the AZ 102 and AZ 104 courses. But every course he took played some role in shaping his career trajectory.

It pays to be a cloud guru

Cloud upskilling has improved Winston’s life substantially. His goal was to triple his wage; he ended up multiplying it by six. Remote work has also afforded him a ton of flexibility: “The fact I can permanently work from home makes my life so much better.” London public transportation leaves a lot to be desired for Winston, and being able to “do work without worrying about travel, or whether my train’s canceled or not” is a game-changer. “I can't think of one negative thing about cloud,” he says. In general, what makes Winston proud is how he “wrote my own personal success story. I want to make sure that I can pass it down to my brothers, and make sure they can build themselves good careers, because it's not always about myself.” 

By no means does Winston want to restrict his knowledge-spreading to the family. He hopes to start a monthly AWS group in his area, where speakers can talk about their cloud experiences and help people get trained. Down the line, he’d also like to create his own digital courses in Africa. “It’s about sharing a common goal and a destiny together.

Looking back, Winston puts a heavy premium on the hands-on learning ACG provided him. “If I didn't run into ACG, I think my journey would have been a lot tougher. I think that the help that I got through ACG was phenomenal. I think that it made my journey a lot more pleasurable. With the way my life has skyrocketed in every single aspect, I've got nothing but love for ACG and Pluralsight.”


ACG and Skills have empowered Winston to advance his career journey; we hope they inspire you to take the next step on yours. 

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Winston Smith with his family