May 19, 2021

How to Pivot Careers Successfully


Episode Highlights

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Looking to make a career pivot? Maybe you aren’t sure how to do so.

Leah Dugan, recruiter at Hirewell spoke with Jennings Wynn, Enterprise Customer Success Manager at SmartRecruiters about his career pivot from the art world into the business world. They share insights on the best practices for pivoting successfully.

Among those are: – Understanding what skills sets are transferable – The importance of translating and communicating your experience to seeking employers – Understanding how to use LinkedIn and other social media platforms to advance your job search – Using networking skills to build connections and your foundation to pivot

If you are interested in learning more or have any questions, feel free to reach out to both Leah and Jennings.

Episode Transcript

Welcome Jennings Wynn! Thank you so much for joining me today. I wanted to chat with you and get your expertise on a topic that is near and dear to my heart, career pivots and how to do so. I know that you have experience with pivoting from specifically from theater to the business world.


And so I wanted to pick your brain a little bit in this chat and get your thoughts on how one might do so, but first I want to introduce myself and let you introduce yourself. My name is Leah. I work at Hirewell. I am a recruiter there and I also do some partnership development and some DEI work and some content creation, general Jill of all trades.


Again, thank you for joining me. I’m going to throw it over to you and let you kind of do a little intro for yourself. 


Wonderful. Thank you so much for having me! Obviously this topic is very near and dear to my heart as well, coming from a career pivot myself.


As Leah mentioned, I’m Jennings Wynn. I work in the software as a service human resources, talent acquisition space. So while I don’t directly recruit, I work in the business world with a heavy focus on human resources, as well as doing a lot of diversity equity inclusion work, working with employee resource groups, sitting on DEI councils.


So very similar passions here. So I’m so thrilled to be chatting about this topic. 


Awesome. Excellent. As I said that kind of general topic is career pivot specifically maybe artists to business world, since that’s where your expertise lies and your experience lies. So tell me a little bit about that.


 What’s your story framed with kind of that topic? How’d you do your career pivot and sort of just a little bit about yourself? 


Yeah, absolutely. I mean, just a little personal background. I am a Southern by birth and Chicagoan by choice. So I spent years and years being a musical theater performer from community theater all the way through college, through a number of years, past college.


And I got to the point where it was time for me personally, to move on. That isn’t to say every artist needs to move on. That isn’t to say that everyone who does a pivot, that they need to give up on what it is that they love to do. So I just want to qualify everything that I say here today with that.


So when I made the decision that it was time to move forward out of the hospitality industry, juggling shows, I wanted insurance, 401k, that kind of stuff. I’ll be honest, it wasn’t the easiest thing. So a lot of what I’m going to talk about today is what I’ve learned and in the hopes that it saves other people some time and struggles.


So I started in the call center, which is where you hired me. And then that sort of put a bit of a proof in the pudding that I could work in a business environment. At the time I was trying to go right from hospitality into business. I didn’t know the lingo. I didn’t know how to make that transition.


So I had to do a bit of a catch step, in order to have not a restaurant at the top of my resume, which isn’t necessarily what everyone’s going to have to do. But with something I had to do, and that’s what led me into HR tech sales, which then led me into an industry called customer success where I’m more focused on configurations and the relationship with the client.


And honestly it was my hospitality background that taught me how to do those technical configurations because I ran those point of sale systems, but we’ll get into that kind of translation here in a minute. That is how I ended up here and then found a love for diversity, equity and inclusion. Actually got my certification from eCornell this past year in order to expand that knowledge.


And I founded a number of employee resource groups. And I guess I found a new passion and being a people person, I guess. 


I love it. Excellent. Well, I love to sort of talk a little bit about since right now, because of the pandemic and COVID, so many folks have had to – have felt like they needed to do a career pivot because their industries just aren’t thriving in the way that they were pre pandemic and they’re not able to find work.


And if they are able to find work, it’s not the same level of commitment. It’s not the same level of cashflow coming in for them. So a lot of folks are like at a place right now where they’re really looking to do a career pivot. If you can talk a little bit more about your experience, specifically with the transition from an artist – you’re still an artist but you know, a working artists to working in the business sector.


Yeah, absolutely. And it’s that struggle that these artists, friends of mine had that really inspired me to start trying to put my experience down on paper and having interactions like this because so many people just didn’t know or don’t know how talented that they are. So I definitely felt a bit struggled and like a fish out of water.


And thankfully I had really great people around me who were in the business world and who helped me with my resume. The number one thing that I felt, that I also hear from performers is “I don’t have any skills.” And the reality is that you do and you likely have more skills than you realize.


I referenced a moment ago, point of sale systems. So when I was interviewing for a technology company, I was like, I have no technology experience. Except I did. I configured the back end of restaurant front ends. If you know anything about the human resources technology space is basically the recruiter backend and the candidate facing space. It’s all about translating and understanding how to translate.


And that’s how I was able to get into the tech world and kind of grow into this business and tech space, was learning how to translate those skills and phrase those skills for that foundation. And I continue to do that. Even those skills I’ve learned now are technically business skills.


It’s all about how you phrase them in order to market and present yourself accordingly. Another example that I like to use is for actors, if you’ve ever had to fundraise, that’s fundraising experience. If you ever had to run the budget, the costume budget for a show, that’s budgeting. You probably did all of this on the G suite and the Google drive.


All right. So you’re G suite proficient. And so it’s really taking, just thinking about the things that you’ve done in every single role and bringing that to the table.  The business world, when you can speak their language, you don’t necessarily have to come from their background. Right. You just need to figure out how to speak their language.


 Whether it’s you just need a day job, whether you’re doing a full pivot, that’s just going to make you more and more successful in that transition, if that’s a transition that you choose to do. 


 I think that’s key really like there are so many transferable skills, right?


So many overlapping skills. The Venn diagram, I feel like skill-wise it’s pretty big. It’s just a vernacular and how you phrase that skill set and how you put it on your resume and how it’s written on their resume, because it’s a completely different culture.


It’s a completely different language. They’ve got their own buzz words, independent of each other.  So it’s just a matter of getting used to how to phrase things so that when someone reads it, it’s translating it really. It’s like a code switch. 


Yes, it absolutely is.


 For my fellow actor friends out there, when you talk to your civilian friends, if you say “We’re getting the show on the boards” they don’t know what that means. So just think about it in reverse. Give them the language that they understand and also don’t sell yourself short.


Totally, and from my experience, going from the restaurant industry and working for years and years and years and years as a bartender and server, there were so many transferable skills that I just didn’t realize I had until I spoke to someone and they were like, “Well yeah, you have customer service skills, you deal with customers all day long.”


I was like, all right. It didn’t occur to me, you know? Like it didn’t occur to me.


I would never be able to work with kind of the global clients that I do, had I not been a server and a bartender. And that is a skill that is really valuable in the business world. There is something special about that outsider perspective.


Even if you do start by feeling an outsider, because it’s a fresh set of eyes and it really can make you stand out in a good way. 


A hundred percent. Okay. Well, we talked about language and kind of how to reframe your skill sets. Are there any other tips and tricks you can clue people on how to kind of make themselves more hireable?


Here’s my big one: LinkedIn. I know everyone listening to this is going to go another social media. It’s not a social media, it’s a business media. This is the brass tax talk that I really have to have with all of my artists and performer and friends that are pivoting.


You cannot just put a photo and a resume up on LinkedIn and expect anything in the world to happen. Yeah. The algorithms for that website are built on usage. It’s very much like an Instagram.  You don’t necessarily need to be like creating podcast level content. You need to be logging in once a day.


You need to be following the businesses that you care about or brands that you either want to work with or enjoy purchasing from. You need to add every person that you possibly can. The great thing about LinkedIn is there’s lots of people that you might end up adding on LinkedIn, that you would never think about adding to your Facebook.


So look past the Facebook list into some of those other people, professional contacts. Like and share posts and create your own posts, if at all possible. If you’re just not interested in adding other posts, I get it but at least share and like because that is what puts you to sort of bubbling up to the top of a recruiter’s search.


If you haven’t logged in or had any activity in that website in three months, you don’t even show up in a search, even if you’re perfect for a job, right. For those of you who aren’t familiar with recruiting that are listening, recruiters log in, they come up with a keyword like sales, Chicago, four years of experience, and then they get resumes and they flip through them at about three seconds a pop.


You’re just not in that stack or you’re on page five, page 10. Think about a Google search. How many times do you get to page five or page 10 in a Google search before they’ve already served you what you’re looking for.? Yeah. And so maybe take that time that  you feel isn’t all that great on another social media site where you’re maybe fighting about politics or even a dating app that might be making you feel bad about yourself and reinvest that time into something that might get you forward and provide value.


And also, you might make new like-minded friends to have like cordial and adult and intellectual discourse with, which I don’t find on any of the other sites. 


Yeah. I was going to add in the networking piece to that because commenting on other people’s posts, following people, doing all these things, where our ability to physically network right now is so hamstrung and that is such a huge part of potentially getting your foot in the door,


especially if you’re someone that might not have the exact background that they’re hiring for, right. You might be great for the job, or it might be something that you can do, it might be something that your skill set actually aligns quite well with but if you don’t have on your resume bulleted specific experience, it might be


a little bit harder to kind of get your foot in the door, right? And having that personal connection where you connect with someone online and they recognize your name and then they see your name on that resume, they’re going to pay attention to that resume if they’ve interacted with you online. Like they just are it’s just how it works.


Or they’ll forward your resume as a referral and advocate and even say, “All right, I know this person, they don’t have all 120 bullet points that you need but they’ve got 80 of them and they’re smart and they’ll ramp up and they’ll work hard. And then you missed that opportunity if you haven’t connected with that person.


 Exactly. Do you have any final words of wisdom? Anything else you’d like to chat about? 


Absolutely. I would just say, don’t be afraid to bring your whole self to an interview. Of course you want to remain professional, but you know if you’re someone heavily tattooed with funky glasses and painted nails and very openly gay or whatever you may be, if you hide that on the phone screen, if you diminish yourself, you’re doing yourself a disservice.


Because chances are, if a company needs you to do that, they’re not the best fit for you and you’re not going to be happy, particularly if it’s a longterm pivot. I mean if it’s a short-term, you might be able to do it. But also personalities like artists have standout. There are many, many people who look like and think like and have a similar degree and that doesn’t diminish their skillset or their talent


but when a breath of fresh air walks into a room or onto camera, people feel it and it causes a very special impact and excitement in the company. So you really are your best asset and really the only person standing in your way is you. 


Wonderful. Well, thank you so much for your words of wisdom and for your advice.


And I’m really glad that I got to sort of get your take on this. I think right now, a really prescient topic. I think a lot of people are thinking about it or currently actively struggling with trying to make kind of a career pivot and how to go about doing so. So, Hopefully your words will be helpful for some folks.


And thank you so much for your time. It’s was so nice to see you. It’s always so nice


All love! 


Thank you all for joining us.  If this was interesting to you comment, like, share, this video and stay posted for more videos of the like! All right. Take care. Bye-bye.


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