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A Career Change to Tech Is Easier Than You Think — Follow These Tips

Ebony Beckwith and Trailblazers
Ebony Beckwith discussed making a career change to tech with two Salesforce Trailblazers.

Salesforce Chief Business Officer and CEO Chief of Staff Ebony Beckwith chats with two trailblazers on how they made a career change to tech and succeeded.

Some people enter the technology world and often start coding or forging a path to work in that industry at a young age. But that’s not the case for everyone. Some people have a total career change to tech and start working after having a job that has absolutely nothing to do with technology. That’s not to say skills they learn along the way won’t help once they pivot and start on a new path. 

That’s exactly what happened with two Salesforce Trailblazers. Cheryl Feldman started her career as a hairdresser before entering the Salesforce ecosystem. Aaron McGriff had a decade of experience in retail before discovering Trailhead, getting certified as a Salesforce Admin, and eventually working as a Salesforce Consultant. 

Salesforce’s Chief Business Officer and CEO Chief of Staff Ebony Beckwith invited Feldman, now director of product management at Salesforce, and McGriff, now a senior consultant at Slalom, a consulting firm focused on strategy, technology, and business transformation to chat with her on the latest episode of #BossTalks on Salesforce+. They discussed their stories and tips for making a career change into tech. 

Scroll down to read the transcript and watch the episode of #BossTalks.

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Success doesn’t always require a four-year degree

Feldman started her career working as a hairstylist, but always had an interest in technology. She then became a secretary, where she learned new skills like analytics and data collection. This led her to want to become a Salesforce Admin. She then approached a startup she found on Craigslist. When she felt they were unsure of her skills, she flat-out asked, “What is your biggest problem in Salesforce? I bet I can solve it.” She then worked the next day for free, locating the company’s Salesforce issues and got the job. “I proved I could do this job just as well as anybody with a master’s in computer science,” Feldman said. 

McGriff, on the other hand, intended to continue studying engineering in college when his boss at Target, where he had worked during his last two years of high school, offered him a promotion and more money. “Like a typical teenager, not thinking things all the way through, I went the route that was giving me the money right then and there,” McGriff said. He stayed with Target for a decade and worked at Home Depot for two years when he realized he needed a change and discovered Salesforce — and so much more. “I got more than a job,” he said. “I got a whole new lifestyle.”

The point? Don’t limit yourself if you think you want to make a change, no matter how different it might be from your current situation.

I proved I could do this job just as well as anybody with a master’s in computer science.

cheryl feldman, Salesforce director of product management

Tips to follow your passion to a new career

Many people want to change careers, but may not know exactly what they want to do. Feldman said to think about what drives you and what you’re passionate about. Then find people who do that, whether in your network on LinkedIn or through Google. Reach out, ask people questions, and seek advice. 

“I would say 99% of the time, folks are willing to have conversations with people who are interested in doing careers just like them,” Feldman said.

Sure, there will be people who say no and people who will say you can’t do something. But for every person who says no, Feldman said, someone will say yes — and it’s important to find those people who support you.

“If you believe you can do it,” she said, “you do it.”

Be intentional, find a mentor, and set goals

Starting on a new career path doesn’t always come easily and likely can create fears. That’s natural. But if you’re intentional and seek out realistic roles at companies, you can learn and grow, Feldman said. She added a mentor can help you achieve your goals of finding success in your new career. Setting measurable goals, McGriff added, allows you to challenge yourself and then celebrate your wins along the way. 

“Believe in yourself and believe in what you can accomplish,” McGriff said. “You never really know what you can accomplish until you actually give yourself the space and opportunity to do so. Believe you can get wherever you want and just keep moving forward.”

Use that time to level up your expertise and flaunt that in your interviews.”

Aaron mcgriff, Salesforce consultant at slalom

Capitalize on resume gaps

People take breaks in their career, sometimes against their own choosing. Eight months after leaving retail and entering operational management, McGriff was laid off. He set his sights on Salesforce. He had been unemployed for more than a year, but used that time to study, earn badges and certificates on Trailhead, volunteer, and build projects to get ready for his next position, whatever that was. When it came time to interview, he was honest about the time he wasn’t working.

“When I actually started saying what really happened, people understood it,” McGriff said. “So me being laid off wasn’t out of the ordinary. I focused on what I was doing in the meantime. Use that time to level up your expertise and flaunt that in your interviews.”

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Watch the full conversation:

And read the full transcript from the show:


Hello everyone, and welcome to Boss Talks, a series featuring candid career conversations with people who are changing the game in their respective industries.

For today’s episode, we’re going to do something a little differently. We share a lot of tips and tricks on Boss Talks for how to build your career, but I thought it would be really helpful to hear from folks who are actively putting these tools into practice.

Not everyone starts out in their dream job, but everyone starts somewhere. So today is about honoring where you are in your journey, and helping you identify your next best steps to designing a career that you love.

So without further ado, I am so excited to introduce my first guest, Director of Product Management at Salesforce, Cheryl Feldman.

Cheryl, welcome to Boss Talks.


Thank you so much Ebony for having me. I’m really excited to be here.


I couldn’t be happier to be chatting with you. So Cheryl, before we dive in, I want to give everyone an opportunity to get to know you just a little bit better, because I still remember the first time I heard your story, and I remember being so inspired. So will you share a bit about your background?


Sure. So currently I am a director of product management here at Salesforce. However, most people don’t believe this when I tell them this, that I do not have a background in technology at all.

I actually started my career as a hairdresser, but I was always super into technology. I was always really interested in it and I was always interested in the next big thing. From being a hairdresser, I then went on to being a secretary and I picked up very quickly when somebody left the organization, how to do analytics and how to combine all sorts of data.

I wanted to be a Salesforce admin so badly, and so I walked into a startup that I found. They had a posting on Craigslist, and I could tell that they were kind of debating, and I flat out asked them, “What is your biggest problem in Salesforce? I bet I can solve it.” And I worked for free the next day, and figured out their issues with Salesforce and proved that I could do this job just as well as anybody with a master’s in computer science.


And I just want to point out for everyone, again, just double clicking on this, that you did all of this without a degree, and I think that so many people think that a four year degree is the only way to achieve success, but you are living proof that there are so many different pathways, and I really admire the grit and determination you’ve brought to your career.

Now, sometimes people know their current job isn’t working for them, but they don’t know exactly what they want to pursue. So what tips do you have for people who want to pursue a different career path?


So my tips for choosing a different career path would be, if you’re not exactly sure what you want to do, think about what you’re passionate about. Think about what you could do around your passions. And if there’s a specific career that you’re passionate about, find somebody who’s doing that type of career now. You can search for things like this on LinkedIn, or just do a Google search, and reach out to somebody. A lot of times, I would say 99% of the time, folks are willing to have conversations with people who are interested in doing careers just like them.


That’s absolutely right. I wouldn’t change a thing about what you said. Great advice. Now I want to switch gears and talk about making an actionable plan. So once you decide you’re ready to move on, and you figured out where you want to go, what’s your advice for how to take that next step?


So first step is be intentional. Be intentional about everything that you want to do. I actually decided back in 2007 that I wanted to be a product manager at Salesforce. However, I didn’t have the exact right skills to get there yet, so I asked people doing that type of role, what skills do I need? And I started finding roles in different organizations that I could take on that would get me the skills to get where I wanted to go.

Step two would be mentorship. Find somebody to mentor you and somebody who’s going to help you and hold you accountable. That is the most important thing a mentor will do, and they also can help you work on skills.

And then the third tip I would give is to keep on checking in with both yourself and your mentor, and make sure that you still want to be on the same path, because I also changed paths a little bit. At one point, I was trying to be a developer and I was thinking that maybe where I wanted to go, and then I really started thinking about it, and really product management was where I really wanted to go, but constantly have those conversations with yourself.


That’s great. And you know, sometimes Cheryl, the hardest move can be the first move, because the fear can be really real. I remember personally when I was switching from IT to a new role in philanthropy, I was terrified. I thought I was making a huge mistake. So what is the scariest part of it for you, and how did you overcome that fear?


I think the scariest part for anyone taking on anything new, whether it’s a new job, moving to a new city, is the unknown. And I think being able to reduce the unknown, and I think also owning your fear sometimes and owning what is making you scared, and then listing those things out and saying, “Okay, is this a rational fear? Or is this me just getting in my head?”


Like you just said, we sometimes can psyche our own selves out. We let the fear get the best of us and we can even talk ourselves out of trying something new. So what tips do you have for reeling in that negative self talk?


I would say, surround yourself with people that believe in you. I’ve done this. I call it my circle of trust, and I talk with these people all of the time, and I will tell them when I’m not feeling confident about something, or I’m scared or I’m afraid. When the opportunity came up for me to potentially come to Salesforce, I was scared. I was afraid. What if I don’t do a good job? And they were like, “You have all of these skills. You are so great at this. You’re amazing at this. You’re going to be incredible at this.”

But they’ll also be very honest with me and tell me if I wasn’t going to be that great or that incredible. And so I think it’s having that core group of people that you can rely on and help build you up and make sure that you have support along the way.


I love that. Now, Cheryl, let’s talk about the naysayers, because sometimes there can be people in our lives who tell us that we can’t do something. Did you encounter this? And if so, how did you handle that?


I had so many people in my career, in my life, tell me, “No, you can’t do this. You won’t be able to do this. You don’t fit the mold. You don’t have this, you don’t have that.” But I will tell you, for every single person that says no, there’s somebody willing to say yes.

So you may get rejected. You may be told no, there may be people out there saying, “She won’t do it. He won’t do it. They won’t be able to accomplish it.” If you believe you can do it, you do it. It’s just finding those people that are going to support you and support your career.


That’s right. And let those haters be your motivators. So Cheryl, you’ve gone from, I love the term you used, also admin to now the director of product management at Salesforce. It’s so exciting to hear a little bit more about your journey. Now, though, it is time for our final question, and my favorite question. So are you ready?




All right. I knew you would be. Cheryl, what is your superpower?


I like to call myself the master connector of great people. So my superpower is networking. I love talking to people, I love meeting new people, and I love hearing about other people’s stories. I love connecting people and seeing them be successful.


I love that, and it certainly is your superpower. I’ve seen that in action. So Cheryl, thank you so much for joining us today and sharing your story. It’s been such a joy to watch you grow in your career.


Thank you so much for having me.


And now we’re going to bring in our second guest for today. So please join me in giving a warm welcome to Senior consultant at Slalom, Aaron McGriff. Aaron, welcome to Boss Talks.


Hi Ebony. Thank you for having me.


Oh, it’s so good to have you here. Now Aaron, you also have an extremely inspiring story and you’ve been so open and authentic in sharing your experience. So I’d love for you to share some of that with us today. Will you tell us a little bit about your background?


So I started working in retail when I was 16. I got my first job at Target. It was just a job so I could have money in my pocket, keep gas in my car, all that good stuff. I stayed there for my last two years of high school.

After I graduated from high school, they actually gave me a promotion. They threw more money at me, so me, college freshman, I’m making pretty good money. I still had to take my classes, at the time I was actually studying to be an engineer, and I kind of had a decision to make. Do I want to take on this full load of engineering classes, or I’m making pretty good money right now, do I want to just continue down the path I’m on? And like a typical teenager, not thinking things all the way through, I went the route that was giving me the money right then and there.

I ended up doing that for over 10 years. I spent 10 years at Target. I spent two years at Home Depot. And after 12 years of that, I knew that I had enough, and I wasn’t living my life on my own terms. So I said that I’m going to get out of retail, I’m going to do something different. Did not know what that different thing was, but I knew that there was something better out there for me. So I went towards it.

I ended up leaving Home Depot and getting a job in operational management. So I’m getting to know my job. I’m getting to know my team. I had been there for about eight months, and literally out of the clear blue sky, I got laid off one day.

During that time, I learned about Salesforce through a family member who just so happened to be in town, and I knew that I was going to give this Salesforce thing a try. And I got a job. I got more than a job. I got a whole new lifestyle.


Aaron, I know from my own personal experience that it can be very intimidating to interview for new jobs while you’re unemployed, and then you have to explain why there’s a gap on your resume. Like you said, it can start to mess with your head.




What’s your advice for people who are currently in that position and on the job hunt?


Honesty is your best policy. I went into interviews trying to finagle my way out of saying I was unemployed, but when I actually started saying what really happened, people understood it. A lot of people were going through hard times, a lot of companies were laying people off. So me being laid off wasn’t out of the ordinary. But what I focused on was what I was doing in the meantime.

So yes, I have been unemployed for a year or more, but in this time I’ve been studying this, I’ve picked up these certifications, I volunteered here, I built these projects. This is what I’ve done to get myself ready for my next position. I haven’t just been sitting around doing nothing. And honestly, I had a one on one interview where after walking through a scenario with a potential employer, they gave me the feedback that I explained that better than people that had been in that company for 10 years. So use that time to level up your expertise and flaunt that in your interviews.


I know Aaron, there are a lot of people who are tuning in right now who are thinking about making a change. What are some good, actionable steps when you’re exploring a new industry or maybe even a new career path?


Absolutely. First thing is, do your research. Don’t just jump into something because somebody says it’s a good thing. And then, set measurable goals for yourself. If this is a totally new industry for you, you never touched anything in it at all, set goals and then celebrate your wins. Celebrate the first time you build something right, celebrate the first test that you pass. Celebrate those small wins and then really set long term goals for yourself so you can make sure that you’re continuing down your path.

The biggest thing is just to really believe in yourself and believe in what you can accomplish. I never thought that I would be here. I never thought that I would be able to do any of these things, and I surprised myself day by day. You never really know what you can accomplish until you actually give yourself the space and opportunity to do so. So believe that you can get to wherever you want to get and just keep moving forward.


Our community is so important to our journey, so what tips and advice do you have for getting more plugged in and finding that support?


So one of the things I love about the Salesforce community is the fact that there is an actual community.

When I first got started and didn’t know anything, I was on Twitter talking about my journey and talking about what I was trying to do, and the outpouring of support that I got was instantaneous, for one, but it honestly was overwhelming that there were so many strangers that didn’t know me at all, but were invested in my success.

They gave me their phone numbers. They gave me resources. They coached me, they taught me. Some of them yelled at me. I won’t say your name, but you know who you are. That’s really what drew me in.

There is so much support in this community that you won’t be able to fail because there will be so many people holding you up and pushing you until you reach your goals. So if I can’t give any other advice, get connected in the community. Find yourself a local user group, and even in these COVID times, a lot of the user groups are virtual, so you don’t even have to necessarily be in the area that you live in. You can join a user group anywhere, but just connect with like-minded people that want to see you succeed, and that will help you.


All right Aaron, final question and my favorite question. What is your superpower?


I think it’s definitely finding the good. There are a lot of things that go wrong in life, but I’m a firm believer that everything happens for a reason. Be it good or bad, everything happens for a reason, and it’s up to you to find the lesson that is in whatever it is you’re going through, find that good and be able to push forward.

I went through some hard times. Losing my job. I had to sell my first house because I was unemployed for so long, but because I found the good in those situations and I found ways to move forward, I was able to get into a better place, and I’m literally in a better place because I’m sitting in a house that I just moved into Thursday because I was able to buy another house because all this just went right. Because I stayed focused, because I stayed motivated and because I pushed towards those goals I had for myself. Yes, I had to sell my house before because I was unemployed for so long, but now I’m in a better house.


I love that, and I love that superpower. It is perfect for you. So Aaron, thank you so much for sharing your story with us. Your experience and advice are so relevant, and I know they’re going to help so many people along their journey.


Thank you, Ebony.


I know this is a popular topic with all of you, so let’s hear your questions.


Hi Ebony. I’d love to ask your advice on how you manage to handle the parts of your job that you don’t love that much with the parts of the job that you love a lot. How do you strike that balance between business needs and personal passions?


Great questions, Debbie, and I’ve thought all lot about this over the years, and where I landed is pretty simple. That is, it’s called work for a reason. I’m ultimately here and getting paid to do all the parts of the job, the good, the bad, the ugly. And every week when I cash my paycheck, I’m saying I’m committed to doing all parts of this job.

So trust me, there are parts of my job that I like to do very sparingly, and parts that I wish I could do all the time, like this. But at the end of the day, striking a balance means that I have to put the business needs first, always. I have to prioritize what I’m being paid to do, and the rest is just icing on the cake. I think the good news is that we can balance and do all of it, we just have keep everything in its proper place and proper proportion. Thanks so much again for the question, Debbie.

Thanks so much for sending us your questions and please keep them coming. I’d like to include a couple each episode, so be sure to mention us in the comments on our LinkedIn page, or send me a tweet at @EbonyBeckwith using #BossTalks.

Well, I hope you all really enjoyed today’s conversation. To watch more episodes of Boss Talks, check out the new Salesforce/plus, and to continue boss building head on over to to join millions of trailblazers who are learning relevant skills, connecting to fellow trailblazers, and giving back with the trailblazer community. With that, thank you all for tuning into Boss Talks and we’ll see you all next time.

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