Rippleshot’s Kaleigh Simmons on Launching a Marketing Career in Tech

marketing career in chicago

Kaleigh Simmons is the Director of Marketing at Chicago fintech company Rippleshot. A classically trained journalist-turned-full-stack marketer, Kaleigh also a graduate of our full-time marketing bootcamp-turned-award-winning instructor.

Our Student Choice Awards recognize the instructors whose teaching and mentorship was voted most outstanding by the students in that track. At our most recent Talent Expo, Kaleigh and co-instructor Eric Pitt took home the Student Choice Award for their two-part Introduction to Marketing. As Carlin Thomas, our program manager in Chicago describes,

Kaleigh and Eric are dynamic duo. They give copious feedback to students on their marketing plans and truly engage with them, making themselves available long after their sessions to continue helping them to refine their plans.

I gave Kaleigh a call to learn more about her marketing session, how she launched her own career in marketing, and to gain insight on getting a job in Chicago’s tech ecosystem:Insights on Launching a Marketing Career in #ChicagoTech from @kaleighsimmons of @Rippleshot Click To Tweet

Kaleigh Simmons and Eric Pitt accept the Student Choice Award for Outstanding Marketing Instructor

Q: You and Eric kicked off our fall 2015 marketing course in Chicago with an introduction to building a marketing plan. Can you tell me about that session?

A: Sure. This session came about over a year ago. At the time, the introduction to the marketing track dove right into technical skills, but I think the staff realized pretty quickly from student feedback that it was more helpful to first get an overview of the discipline holistically before diving into individual topics. That was what we derived this lesson from.

The intention is exactly that holistic approach. Eric and I don’t get too into the weeds on any topic. Instead, we start with an overview of each marketing topic the students will delve into over the course of the eight weeks. We cover a little bit of SEO, a little bit of branding, some content marketing, social media, and a bit of analytics. Then, we ask them to take all those pieces and design a marketing plan for a business.

What we find is, although the students always struggle, the difficult pieces start to really click once they begin to dive deeper into the individual marketing lessons, because they’ve taken a crack on it early on. A number of students have taken their marketing plans and used them to pitch for jobs because they’d been refining them throughout the course of the program, which I think is awesome..@kaleighsimmons + @SuperBad_ 's intro to #marketing @StartupInst is practical +holistic Click To Tweet

Q: That’s excellent. What do you think made your session and teaching-style is so effective?

A: Honestly, I think it’s because Eric and I are friends in real-life, and we’ve done this session with five or six groups now, so we’re really comfortable with it and we keep it upbeat. I’ve been through the program, so I know how intense that first week can be. It’s very overwhelming, so it’s great to have people come in and level with you and be laid-back. We really do try to make it fun. We tell really cheesy jokes.

We always re-engage with students a few weeks after the lesson for coffee chats and to work on their marketing plans with them. We know that many of them will use their marketing plans in their job interviews. If we can help them get further down that path, then we’re happy to do it. Eric and I are genuinely excited to work with Startup Institute students, and we always have a blast. It’s never a tedious thing for us.

Q: I am so glad to hear that. It’s exciting to have an alumna of our marketing course win the Student Choice award. Can you tell us about how you got to where you are today?

A: Sure. I’ll dial it back all the way to college. I went to journalism school at Syracuse University—one of the most prestigious journalism programs in the country. If you want to talk about the pressure of a graduate to move into that career path, it was intense. A lot of my fellow classmates are now at NBC, ABC, or ESPN. The assumption is, when you go through that program, you’re going to go on to do amazing things in the journalism industry, and then in 10-30 years you’ll have your name on the Wall of Fame.

I came out of school with this task in front of me—I was going to be the next Katie Couric or Ted Koppel. But, then I realized—I didn’t really love it in real life. I didn’t know what my next move would be, but I had to pay off college loans, so I ended up taking an administrative job at a manufacturing company. Talk about a fall from Grace, right? I went from wanting to be Katie Couric to this administrative role at this stodgy old company that was not me and not what I wanted to do.Shortly after I finished school, I realized #journalism wasn't for me, says @kaleighsimmons Click To Tweet

I stayed there for a while. I moved through forecasting, and supply chain management, analyst work, and the product development process. I realized that I didn’t like to do any of it. I wanted to make a change, I really wanted a job in the tech industry. My skill set was applicable to marketing, and at the time I was running my own freelance writing business. I couldn’t really make what I wanted to happen work in Rochester, NY.

I think I literally Googled “tech industry” and “Chicago,” and Startup Institute showed up. They were brand new in Chicago at that point. I got in, and I decided that that was my sign. I quit my job, sold half of my belongings, packed up my car, and moved halfway across the country having never even visited Chicago before. My first day here was two days before Startup Institute started. It was bananas. But it was probably the best life decision I ever made. And that’s what got me here.Moving to #Chicago + doing @StartupInst was probably the best decision I ever made, says @kaleighsimmons Click To Tweet

Q: That was a bold move!

A: It was a pretty bold move. I had a little bit of marketing experience in that last job in Rochester, but nothing really that could propel me into the type of role that I wanted here. I was going to be in the first class out of Chicago. I had a lot of uncertainty and questions when I quit my job and moved here. But, it worked out.

Q: Ultimately, what made you decide to do it?

A: First, I needed to be in a city that could support the type of ecosystem I was looking for. And secondly, I knew I had a little bit of the raw skills, and I’m self-motivated, but not to the point where I can, for example, sit down and teach myself how to code. I knew I needed to hold myself accountable for building the skills I needed. Otherwise, the transition would have taken me years. Startup Institute was eight weeks, which is a relatively short time investment, but it’s full-time. I knew I’d have 30-60 other people alongside of me, holding me accountable for this journey. I found that really attractive as a way to push myself from where I was to where I wanted to be.I found the short time investment + supportive cohort an attractive option, says @kaleighsimmons Click To Tweet

Q: You took on a director of marketing role straight out of our program. Was that challenging?

A: I was actually the very first hire that that particular company had made. While that title sounds very lofty and like I had a huge staff underneath me, it was literally the two founders and then me—the first hire.

It was harder than I’d anticipated. No matter how well you think you know something, when you actually are forced to execute on that, and you don’t have anyone to ask or bounce ideas off of, it’s really hard. I put a lot of pressure on myself. I’m glad I did it. It was an awesome experience to watch the team grow  and the sales pipeline be built out. It was tough, though.Being the first hire was a lot harder than I'd anticipated, says @kaleighsimmons Click To Tweet

Q: What qualities should aspiring-marketers cultivate in order to be successful?

A: The most important is a soft skill, and that’s confidence. This is the thing I talk most about when I have coffee chats with students. They always ask me a very similar question to the one you asked me just before this, which is how do you end up in a role at a director level right out of this program, and the answer is confidence.

You need to have confidence to go into a job interview and say “Here’s what I know how to do. I know I can crush it in these three areas, and these are the areas where I know enough to get by. I  know enough to teach myself what I don’t know, and I’m confident that if you take a chance on me, I’m going to kill it for you.” Then, you need the confidence to execute. That confidence was the biggest factor in determining my success in that last role, and then again at my current job.Aspiring marketers should, first and foremost, cultivate #confidence, says @kaleighsimmons Click To Tweet

The hard skills will vary from job to job. I can’t tell you that if you become an awesome coder or an exceptional email marketer that you’ll always be successful, because that’s not true. The skills that you need vary depending on the company, the industry, your clients, and what day it is. But confidence will get you far in any industry. People in the tech space are bold and they’re taking risks and they want people on their team who are just like that.Ppl in #tech are bold + take risks—they want ppl on their team who do the same, says @kaleighsimmons Click To Tweet

Q: What would you say is most exciting about working in marketing for Rippleshot?

A: To be honest, I was not, and am still not the hugest fan of Fintech. When I was interviewing at Rippleshot—and I’ve told my boss this—I had some other job offers on the table. At the time, Rippleshot was at the bottom of the list because I thought, “Who cares about credit card fraud?” “Who cares about Fintech and hackers?” I didn’t understand anything about this industry, so Rippleshot wasn’t very attractive to me initially.

What changed my mind was that they’re solving a real problem in the marketplace. If I ask you if your card has ever been stolen, have you ever seen fraudulent charges, or have you ever had to get it replaced, the answer is probably yes. It’s a huge issue that eight people from this little company are tackling.

We have clients and partners who see what we’re doing and believe it’s important and show support for us. And that’s really fun, because the first company that I joined ended up fizzling out. I know what it feels like to be at a startup where you’re knocking on doors and no one is answering. [At Rippleshot] we’re doing insane things that most companies of our size don’t get a chance to do. I don’t take it for granted at all. I’m thankful for that every day.I'm grateful to work @Rippleshot b/c we're solving a real, important problem, says @kaleighsimmons Click To Tweet

Q: What’s most challenging?

A: The biggest struggle is that banking is so highly regulated. We’re trying to sell-into banks, which are notoriously old and stodgy, so that’s really difficult. Marketers want to be able to run with something and test, and then get results and try again. But, it’s a much slower process in Fintech.#Marketers want to be able to move fast + test, then get results and try again, says @kaleighsimmons Click To Tweet

Q: You moved to Chicago to join the tech community. What do you love most about it?

A: I love Chicago tech because the city, in a charming way, kind of sees itself as the underdog. Not in a “Feel bad for us” way, but in that “We know we’re not Silicon Valley, and we’re not New York or Boston, but we have our own unique identity.”

Having grown up in the Northeast, Midwestern charm is a very real thing. It’s a very tight-knit community. Everyone here knows everyone else. There are over 400 companies in 1871, which is the building in which Rippleshot resides, and I could walk down the hall right now and see at least one person that I know. If you ever need help or advice, it’s always available here, and I love this closeness. I don’t know that you’d get that in Silicon Valley. Chicago feels special in that way.I love #ChicagoTech b/c the city, in a charming way, sees itself as the underdog— @kaleighsimmons Click To Tweet

Q: If you were to give one piece of advice to someone looking to get a marketing job in Chicago tech, what would it be?

A: Outside of attending Startup Institute, which is a great catalyst for getting you to where you want to be, your network in Chicago means almost everything. If you want to join the tech scene here, there are a million ways to get involved, a million events on any given night, where you can start to show your face and get introductions to the people you want to work for or with.In #ChicagoTech, your network means almost everything, says @kaleighsimmons Click To Tweet

Q: Can you share a few events that you’d recommend in Chicago tech?

A: Built In Chicago hosts a great monthly event called Built In Brews at different tech companies’ offices. That’s a great way to get to know different companies. My other suggestion would be that you look for events that take place here, at 1871. There are probably hundreds each month. The energy is cool, and the people are wonderful. This is recognized as the central tech hub in Chicago—the more that you can be here and meet people, the better off you are.Want to break into #ChicagoTech? Attend events + meet the people @1871Chicago, says @kaleighsimmons Click To Tweet

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Christine spreads the Startup Institute magic as Marketing Manager. The lead editor in charge of The Whiteboard, Christine's main goal is that our media hub be a digital reflection of our remarkable community—celebrating lifelong learners, innovators, and difference-makers. An alumna of the full-time program, Christine transitioned her career into marketing after four years of teaching high school English in the US and in Thailand. She is an avid contemporary and jazz dancer, a lover of cheese, and believes wholeheartedly that a life without risk is a life without gain. She is always cold; if you stop to visit her at her desk, she'll have a blanket with her—guaranteed.

Rippleshot’s Kaleigh Simmons on Launching a Marketing Career in Tech has 1 comment

  1. February 9, 2016 @ 11:20 am Edwin Plotts

    Great read/interview, Christine. I’m now even more excited to attend SI’s marketing track in New York this spring (only 20 days ’til launch!).

    Kaleigh’s emphasis on confidence really struck a cord with me. It’s something I’ve noticed as a defining keystone in the industry, and one my biggest weaknesses. I’ve been working as a contract Digital Marketing Coordinator for a few months now, and although I’ve seen much success I find myself constantly wondering: Is this enough? Is this right?

    Now I have learned the trade purely by reading books, blogs, listening to podcasts and experimenting, so lacking any upper management or team leads me to feel unsure about my methods/results. But since I’ve started networking with others in my industry I’ve found that most don’t have the answers I seek, they just have confidence. What’s more is that in going to meetups and offering my own insight I’ve had people come to me with questions on how to go about something, or what I’ve had success with, etc. This in particular (having people seek my insight/experience) has helped me further realize just how defining confidence is in this industry. Marketing seems to be almost entirely about making educated guesses, and standing out as a job prospect then is in the confidence one has in their educated guess.

    So for anyone reading this who is struggling to find confidence, definitely participate in local meetups and be sure to offer any insight you might have, ask questions and challenge ideas. You’ll find you know more than you initially thought. 🙂


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