Welcome back to our Meet the Postie series. Each month I sit down with a fellow member of the Postie team to ask them questions about work, life, and everything in between. These posts are loaded with relatable stories, tips on stress management and work/life balance, fun photos, and more. Last month we sat down with Ryan Riggins, the voice behind the Postie newsletters and LinkedIn account. This month you get to meet Jessica Chiero, a stellar member on our sales team! Jessica loves tech, skiing, podcasts, and helping her clients find success. Let’s dive…
Name: Jessica Chiero
Location: Austin, Texas
Title: Account Executive
How long you’ve worked at Postie: Almost 4 years
Favorite Food: Steamed Alaskan King Crab Legs with Melted Butter
If you could travel to space, who would you take with you: My fiance, Aaron. We’ve already decided that if the chance to go to Mars becomes available, we’ll book tickets. Bye, Earth!
Pets: No, but I grew up with animals and I’m a huge animal lover. All kinds of animals–not just the fluffy ones. I had a bearded dragon growing up in addition to two dogs, two cats and four guinea pigs.
Find Jessica on LinkedIn!
What inspired you to join Postie?
I previously worked for another marketing technology company on the paid search side and fell in love with any and all things marketing and tech. Before that, I was in the law industry. The legal world and the marketing world are completely different. I feel like everything in law was extremely antiquated while marketing seems to be coming out with something new on a weekly basis. I’ve always been drawn to things that are more fast-paced, modern, and improving instead of static & regimented. It’s more gratifying to feel like you’re a part of the change (the world of tech) versus stuck in the past (the world of law). I’m speaking from experience. There’s certain things in the legal world that haven’t changed for the past 50 years. However, I’m not saying the past isn’t important. Law and structure are a foundation for everything that we do. I just prefer to be at the forefront of something instead of being further down the funnel. Postie embodies all of these things. It’s taking something traditional like direct mail, modernizing how it’s done through technology, and it’s marketing focused–so it really felt like the perfect fit.
What do you love most about your job?
The people. I’m guessing this is a popular answer to this question, but there’s a reason for it. I’ve never liked who I’ve worked with more than working here. Everyone is extremely driven and smart. I learn something new almost every single day. It’s very inspiring. Postie is also the most collaborative company I’ve ever worked for. I truly feel like each and every one of us is heard and has an impact on the company.
What are you most proud of professionally since joining Postie?
Prior to Postie, I was restricted to only interfacing with the client during the sales cycle and then when it was time for them to onboard, it was also time for me to say goodbye to that client and have them passed on to someone on the client support team. At Postie, we’re hyper-focused on building and maintaining relationships with our clients, so I am still very involved with the account once they sign on. I
have found this to be tremendously rewarding not only because I’ve had the chance to learn the account management side of the business (when other new business individuals sometimes never get this opportunity) but also because I’ve been directly involved with seeing specific accounts absolutely flourish in direct mail as a channel.
It’s basically like having the opportunity to watch the person enjoy their car after they’ve purchased it and ride along in the passenger seat as they experience all the things they thought they were going to get and more.
I’ve worked at other organizations that have had very obtuse sales tactics to get clients in the door and it never sat well with me. I am proud to work for an organization that not only delivers what it promises but also continually looks for ways to go above and beyond to make our clients happy. And to have the opportunity to be there for all of it, from the planting of the Postie seed until it’s fully blooming into a giant marketing channel is very fulfilling as a sales professional and as an individual.
Why don’t you tell us something about your professional development journey?
Oh, what a journey it has been. I went to school and majored in Tourism Management because I used to want to be in event management. My dream, at the time, was to be in charge of major music festivals like Lollapalooza or Austin City Limits. During and after school, I worked at several music venues responsible for putting on large events like these and even spent a little time as a talent buyer for a music venue outside of Chicago.
After some time, I realized the music industry wasn’t for me and my timing couldn’t have been worse–it was the middle of the recession, and super hard to make a career change. There were no jobs available anywhere. I started working at California Pizza Kitchen as a server to support myself and apply for jobs at the same time. Finally, I found a receptionist position at a patent law firm but when I interviewed, they said they thought I would make a better fit as an account manager and that’s where my sales career began.
After some time there, I realized I was more interested in technology and took a software sales job at a public relations company and then moved over to working in the paid search position that I previously mentioned.
It’s been quite the ride but I wouldn’t change a thing. I think because I’ve gone through so much I’ve developed a wide skill set. I don’t take anything for granted. I appreciate each opportunity I’ve had because I’ve learned so much, and learning is my favorite thing to do.
What have been some of the most important lessons you’ve learned throughout your entire career?
That my job as a sales professional is not to sell, it’s to HELP. If you focus too much on selling—you’re focusing on the wrong thing. The biggest reason why I like my role is that I genuinely enjoy helping people. Postie helps our clients do their jobs better and also makes their workloads easier. When my clients call, they are asking how I can HELP them with something, not how can I SELL them something. I love being their helper and guru for all things direct mail.
What do you think is the most important skill you bring to the table?
My authenticity. People can tell when you’re not telling them the truth or just going through the motions. I go into each of my calls with a mindset of “what can I do to help this particular client?” and “what can I do and say that’s going to build trust?” A big part of this is putting yourself in their shoes and trying to understand where they are coming from, their specific needs, their specific pains, and what’s ultimately going to make them more successful. But I think the key part is figuring out from the client, in a genuine way versus sounding like you’re rehearsed, what is truly important to them.
I personally make an effort to not use a lot of sales jargon in my calls. Phrases like “30 thousand-foot view” or “low-hanging fruit” are good examples of things I try to avoid. I’m sure the person on the other end has heard them countless times and I think it automatically makes the conversation seem less personable and less authentic. And it’s hard to want to work with someone you think is just playing a part instead of actually being interested in solving your issues. Clients can sense this.
What’s your favorite memory from working at Postie?
Our company all-hands meetings have been my favorite times at Postie. I’m actually one of the few people that misses working in an office, but it’s because my coworkers are important people in my life and I wish I got to see them more. Someone once told me they thought it was weird when people didn’t care to form relationships with people they work with because they spend more time with them than anyone else, and I couldn’t agree more. So I’ve definitely loved getting to see people in person versus over the computer screen. I think my older millennial is coming out a little haha!
Do you have any strategies for dealing with stress at work?
Yes. Make a to-do list and prioritize it. It calms me down to write things out in order of importance and it’s always a lot less to manage than the stress in my head was making it out to be. Additionally, checking off the list one by one is very satisfying.
What tips or advice would you give someone starting a new job in your field?
To anyone starting in Sales, I would say handwrite a script and record yourself talking through the script. It sounds simple but we live in a world now where we type everything out and I think we forget how much we can retain by writing things down and practicing like we did when we were young.
It’s also super hard to watch yourself in a recording but immensely beneficial because you’ll notice things that you do that you’re not even aware of like too many filler words or speaking too fast.
What industry changes or trends, do you think will have the biggest impact?
I’m curious how the battle will play out between security and personalization, but I think this is going to be a huge issue in the coming years.
For example, there’s the Internet of Things. We can connect our phones to our refrigerators, our cars, our washing machines, our speakers, etc. And I’m sure data on our habits with those devices are being tracked. But the caveat to this is I’m betting a lot of people do not want this data shared. So there will be some people who would love to have this turned on so companies can see what they are doing and create more efficiencies with their day-to-day, and other people who don’t want companies making suggestions at all.
I personally can’t decide which is better but the internet is already tracking our activity online and on TV anyway, so I see it as no surprise that the next thing to track would be our home devices.
Do you have any mentors, Postie? Or otherwise, who you’d like to shout out? if so, how has this person made an impact in your life?
My dad is my biggest mentor. He’s an entrepreneur who is also named Dave (just like our CEO). He started his own business with his father when he was 19 and I have always been amazed by his work ethic and how he manages things. Over the past 35 years, I have seen him handle so much when it comes to his business, but he’s always maintained a great attitude and treated the people around him with lots of respect–even when things were hard.
I think the true sign of a good leader is what they do when things are tough and how they pick themselves and other people up around them. It’s true what they say, when things are going tough–the tough get going, and I think tough can also mean having a lot of mental fortitude. I’m glad I had my father as an example of how to act in these types of situations.
What do you enjoy doing outside of work?
I absolutely love going to concerts. My first concert was Backstreet Boys when I was 12, and from then on, I was hooked. It’s part of the reason I moved to Austin, the live-music capital of the US. I’ve probably seen over 1,000 shows and I like all different types of music. My favorite band is The Offspring and my favorite artist is Dolly Parton.
What would your perfect weekend look like?
Going to a concert, doing something outside involving water ( that includes frozen water – aka snow). Skiing is hands down my favorite activity but I don’t get to do it a lot given that I currently live in Texas.
I also love going to comedy shows and trying out new restaurants. I am a huge foodie and love the show Top Chef. I’ve already been to every restaurant owned by a top chef contestant in both Austin and Chicago. It’s a bit of an obsession..haha.
What’s something surprising that not many people know about you?
I love karaoke and I’ve won multiple karaoke singing contests. The one I remember most is when I won a Britney Spears Karaoke Contest singing “Oops I Did It Again.” I’ll openly admit that I’m not the best singer, but I do know how to pick the songs that people want to sing along to, which definitely gives me an edge.
Do you follow any sports teams?
The Chicago Blackhawks and the Chicago Cubs. GO CUBS GO!
What types of books or movies do you enjoy?
This isn’t a book/movie but I want to make a shout-out to podcasts. I enjoy listening to podcasts.
My favorite is one called Criminal that describes different types of crimes from all over the world. Not all of them are dark crime–some of them are actually quite funny. For example, one of my favorites is one about a man who hid himself in a wooden crate and traveled all the way from the UK to Australia by plane. That type of thing would never happen today and its funny to listen to all the things that had to happen so that he would 1) make it the whole trip without being suspected and 2) successfully get out of the crate and leave the airport without anyone wondering where he appeared from.
Do you have any creative outlets or interests?
I play the piano, but I am a little rusty. I haven’t owned a piano since moving to Austin. But I’m thinking about buying one soon and starting to take lessons again. I miss playing an instrument.
What’s something you’ve always wanted to try or learn?
I really want to learn how to play tennis. I was on the Badminton team in high school and miss playing a racquet sport. Pickleball looks a little too easy and I’m up for the challenge of tennis.
Another thing I’ve always wanted to do/try is go to Japan. I grew up across the street from The Chicago Botanic Gardens and I used to spend hours in the Japanese gardens there. It’s always been a dream of mine to see Japanese gardens in their native land.
What’s the best thing that has happened to you this year?
Two things, actually. Getting engaged to my fiance, Aaron, and buying my first house!
What’s something that you’re proud of?
I have always loved visiting Austin and said I was going to live here one day. The last time before moving here, I pointed at an apartment complex and said, one day I’m going to live right here in this apartment complex in this city. 4 years later–I moved into that exact apartment without knowing a single person. I started a new life in Texas and it’s so much more than I could have hoped for. So I guess that’s a long way of saying, that I’m really proud I can set goals that might take years to achieve but I am steadfast that I will accomplish them. As they say, Rome wasn’t built in a day. 😉
If you could pick any superpower, what would it be and why?
I think Mystique has the coolest power.
I would love to be able to change into anyone because I could experience what it’s like to be in their shoes and I like that it’s not permanent. It would be cool to switch from being the president to being a DJ to being a cab driver all in one day.
I could travel the world as well by changing into people from different countries. I think it would make me a better person as well to be able to see the world from so many different perspectives.
—
That was fun, Jess! With that, I’ll see you all next time! 🚀
