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Life at UpKeep

Life at UpKeep – John Oriola, Sales Development Representative

Ryan Chan

Life at UpKeep!

We are starting a new employee spotlight blog series called, “Life at UpKeep”, to showcase the amazing people and teams in our company doing amazing work together!

Through the eyes of our very own UpKeepers, you’ll get a glimpse into our company culture, our team’s big and small wins, how members of our team came to join and love UpKeep, and so much more! 


Meet Our Teammate!

We are excited to chat with John Oriola, our awesome Sales Development Rep who truly embodies the heart and soul of UpKeep! John always finds ways to be helpful to his team, takes time to shoutout others, and strives to improve each day. He reaches out to multiple departments to learn about their responsibilities and projects just out of sheer curiosity and wanting to better understand the overall UpKeep picture. Here is his interview with our CEO, Ryan!


Ryan: Hey John! Super stoked to be chatting with you and spotlighting the awesome work you are doing at UpKeep! Let’s kick things off with you sharing more about your role and some of your responsibilities here at UpKeep! 

John: Yeah! So, I am currently a Sales Representative at UpKeep. And, to be quite frank, the role is very different from what I had imagined coming into it. My understanding of salespeople was that they were fancy telemarketers, but I could not have been more wrong. One of my main responsibilities is essentially reaching out to prospects and anyone interested in stepping up their maintenance game. But more so, I have learned that my job is to be a great listener — to listen to what people need and introduce them to UpKeep if I find that our team can provide value to them. A year ago, I never would have thought that being a Sales Rep was to be a great listener. And, this is something that’s been trickling into my own personal life — to improve my listening — because you know me Ryan, you know I’m a talker! 

Ryan: I can totally relate, I’m definitely a talker too! John, I’m super curious about what got you into sales and what made sales something you want to do?

John: I remember briefly talking about this during my interview, but I was at a crossroads in life after college. The day before my LSAT, I remember my cousin, Nicole, coming over and I was venting to her about my inner struggles about post-grad. On one hand, I had spent the past two months studying for this exam, and on the other hand I wanted to start working and wasn’t sure if I wanted to commit to school again. The exact sentence I told her verbatim was, “I just want to be a useful member of society and pay taxes!” She told me more about her role as an Account Executive and about a great company she worked for — surprise it’s UpKeep! And so, I sent in my application! It was really through Nicole that my perspective on what it meant to be in sales changed a lot. 

Ryan: That’s awesome, John! Have you ever looked back and wondered about taking the LSAT?

John: Not at all! I have no regrets. My feelings when I first got the job were just pure excitement, and I felt like I was in the right place at the right time. And, even today, I feel like if I ever wanted to go back to school, the option is always there. But, I’m happy with where I am now, and that’s not something that I felt when I was grinding for an exam that I didn’t know was worth it. This job at UpKeep though is worth it!

Ryan: Nice! I’m really glad to hear that! John, what’s one project you’ve been working on that you are really proud of, whether personally or professionally?

John: I’ve always wanted to start a YouTube channel and create a video diary to look back on. And so, since I have a lot of time now because of COVID, I actually started that YouTube channel with my best friend, Max! We already started drafting some video themes and concepts! So, once our first video goes live, I’ll definitely share with the team!

Ryan: What’s something you love about UpKeep?

John: Honestly, it might sound like such a cliche answer, but it’s the people. I remember when I first started at UpKeep, I would rave to my friends and family about how much I love coming to work! The people that I work with inspire me so much and I learn from them everyday. I was coming from a law background, so going into the sales pit, I had nothing to arm myself with. But, our team supported me a lot, and everyone was so open and transparent in teaching me the ropes. Even during these unprecedented times with COVID, I feel like our company has been thriving, our activity has been higher than ever before, and even our Slack channels have been popping off with daily challenges and fun spiffs! I remember telling my friends that I won an annual Disney Plus Subscription, and it surprised them how I was still really enjoying work during a pretty difficult season for most companies. But, this culture really stems from the amazing team we’ve built at UpKeep! 

Ryan: Well, John, I love having you as a part of the team and loved just getting to know you more! Thank you so much for everything you do! 


Join us for the Next Life at UpKeep!

Every other week, we will be spotlighting a new member of our team! So, stay tuned and hope to see you in the next one!

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