Choose Your Own Career Adventure With These Chicago Companies

Many growth opportunities are awaiting talent across fintech, edtech, IT, e-commerce and more.
Written by Kim Conway
November 1, 2021Updated: November 1, 2021

As the end of 2021 approaches, there’s never been a better time to start thinking about new beginnings. However, whether you’re ready to join a new team, considering making a lateral career move, or entirely new to tech and what it can offer, the starting point of a job search might seem a little daunting.

But take it from Bill Banks, group experience director at Bounteous: It’s not so far-fetched to find companies out there that will support you in a career shift. “Having a growth mindset is important, and Bounteous encourages team members to choose their own career adventure,” he said. More specifically, there are opportunities to transfer between departments or roles, should that level of flexibility be of interest to new hires.

Following a similar thread, companies that prioritize culture and a relationship of trust with employees may offer more flexibility. When Erin Mohideen realized she needed a career change that offered more remote flexibility and balance, she turned to Inspirant Group. A conversation about work-life balance with the company’s CEO was all it took for her to go all-in. As a people and culture lead, Mohideen can now vouch firsthand that her company is one that actually puts its people first.

So, are you ready to choose your own career adventure? We met with employees from 10 companies in Chicago that are looking for new tech talent. Keep reading to find out what these professionals shared about how they’ve grown alongside their companies and what qualities they look for in their future hires. These firms could be exactly what you’re looking for — and you could be exactly who they need.

 

Jennifer Reilly
Director, People Operations

 

Why did you first apply to join your company, and how has your experience changed over time?

I was first approached about a job at Gemini late in 2017, when cryptocurrency was just exploding but still largely unknown. Coming from a traditional private equity firm, I was intrigued by the concept of the future of money and the emergence of an industry that could transform the world of finance as we know it. The opportunity to play a role in building the people function in such a new industry was an absolutely thrilling proposition, and while daunting, it presented a welcome and exciting challenge in the growing fintech landscape.

When I joined Gemini, we were just under 100 people and functioned as a quintessential startup with everyone wearing many different hats to create the foundation for the company that we have today. We are now 625 people with more specialization and enhanced organizational frameworks in place, but we still maintain some of the scrappiness and creativity of a startup. Aside from growth, the most notable change from when I joined Gemini in 2018 to now is that crypto has become far more normalized in our culture and its influence continues to have a global impact. 

Our mission is to unlock the potential of Gemini’s greatest asset — its people — through the development of programs that drive a culture of excellence.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

Given our continued expansion, we are quickly growing the people ops function. As a team, our mission is to unlock the potential of Gemini’s greatest asset — its people — through the development of programs that drive a culture of excellence. I’m lucky enough to work with an incredible team of individuals who are intelligent, driven, creative, passionate, collaborative and curious, and they inspire me every day.

During this stage of immense growth, when I’m meeting candidates to join my team, I look for individuals who possess a keen sense of agility and are willing to proactively roll up their sleeves. The best candidates approach problems with an open and solution-focused mindset and understand the importance of collaboration and communication — both with fellow team members and individuals from across the organization. Most importantly, I look for candidates with different perspectives and experiences to challenge the status quo and ensure that we are always iterating on our current processes to align with the growth of the business.

 

 

Bill Banks
Group Experience Director

 

Why did you first apply to join your company, and how has your experience changed over time?

I joined Bounteous seven years ago when the company was around 14 years old, but still functioned with a start-up mentality. What appealed to me most was the simmering energy and a sense that the company was about to take off and soar — and this gut instinct turned out to be spot-on.

In all that time,  the company’s innovative spirit, the incredibly smart and empathetic team members and the cutting-edge thought leadership in the digital transformation space hasn’t changed. 

What has changed is that Bounteous has continued to experience tremendous growth year after year, which has resulted in a number of exciting advancements as the organization evolves. What started as a small user interface team has blossomed into a full suite of talented creatives across UX, design, content strategy, copy, motion and more. The company has continued to grow and branch out into additional skill sets, which has allowed all of our practice areas to collaborate closely together and shine.

Many people at Bounteous have approached their career paths like traversing a jungle gym, by climbing and weaving into different practice areas based on what excites and interests them.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

A willingness to challenge the status quo and a desire to learn are attributes that come to mind. You can coach someone on tactical knowledge, but you can’t coach character. I seek out people for my team who have a strong point of view and take initiative to solve problems.

We hire subject matter experts in their chosen craft, but we also encourage everyone to use their voice no matter what stage they are at in their career — there are leaders at every level. Having a growth mindset is important, and Bounteous encourages team members to choose their own career adventure. While we do have scaffolding in place to assess career growth and promotions, there’s enough flexibility that no two avenues of growth look the same.

Many people at Bounteous have approached their career paths like traversing a jungle gym, by climbing and weaving into different practice areas based on what excites and interests them.

 

 

Marisa Dottore
Senior Omni Channel Marketing Manager

 

Why did you first apply to join your company, and how has your experience changed over time?

I initially applied because of Peapod’s reputation, but also because working with food is fun and exciting. I have always felt you can market anything as long as you are passionate about the product and really believe you are doing something important. Our company helps feed people. There aren’t many things more important than that.

In the past few years, I transitioned from Peapod to Peapod Digital Labs, and that changed how I think of my role. We now provide the technology that brings groceries into people’s homes. As the world evolves and consumers are looking for an easy way to feed themselves, we bring a critical and much-needed service to East Coast customers of Ahold Delhaize’s brands in the U.S.

The trust you build with coworkers evolves over time and leads to amazing partnerships where everyone can have a voice.”

 

What’s your most interesting or exciting work-related challenge right now, and how are you overcoming it?

One of the aspects of my job I love is working with many players at our sister brands to launch projects or make unified decisions. It’s a challenge in that many players can be involved at all different levels and there are unique customer profiles in the various markets we support, which means it can sometimes be tough to get coordination and agreement when needed. I rely on various methods of communication — emails, meetings, instant messages — and the relationships I have built help me navigate these challenges every day. The trust you build with coworkers evolves over time and leads to amazing partnerships where everyone can have a voice at the table.

 

 

Mike Bourgon
EVP, People & Culture

 

Why did you first apply to join your company, and how has your experience changed over time?

When I began looking for a new role, I made a list of requirements that I wanted my new employer to satisfy. First and foremost, I wanted to work at a high-growth company with a strong mission. I also sought out CEOs with a clear vision and track record of supporting employee success across the board. It was crucial for me to find a company that fosters an open and honest culture while encouraging cross-team collaboration. Elevate K-12 checked all the boxes for me, and I started working there less than three weeks after I applied!

I imagined a high-energy atmosphere with a strong emphasis on individual accountability where things move quickly, and that is precisely how we operate. We make timely, educated decisions and empower our staff to do the same. We always act in the best interests of our students, teachers and staff.

It was crucial for me to find a company that fosters an open and honest culture while encouraging cross-team collaboration.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

There’s a lot to accomplish in a high-growth start-up environment, and because we’re a small team, everyone wears several hats. When I interview individuals, I attempt to gauge how they feel about working in a position where being a utility player — sorry for the baseball reference — is important. This means working as a team, helping one another and occasionally taking on tasks that are outside of their comfort zone. Such circumstances also offer opportunities for workers to broaden their background, develop new skills and grow professionally — all of which are beneficial to our employees, team and company.

 

 

Rasinee Pongchairerks
Vice President, Advice Finance

 

Why did you first apply to join your company, and how has your experience changed over time?

I started working at NextCapital as an intern and joined the company full time after graduation in 2016. I was fortunate enough to learn about the company firsthand through friends who were working here at the time. I was impressed and eager to make an impact on an exciting and fast-moving industry, and that’s why I applied. 

Five years later, I’m still very excited and proud of what we have done and will do. We launched our product and have helped many people plan for their retirement. In that time, I have worked with many talented people and made lots of good friends. It has been a great journey so far and it’s my pleasure to witness the company’s growth and success.

The main traits we look for in candidates are a positive attitude, intrinsic motivation, good communication and adaptability.

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

When I’m looking to grow my team, I’m looking for soft skills. The main traits we look for in candidates are a positive attitude, intrinsic motivation, good communication and adaptability. 

A positive attitude keeps you motivated, eager to try new things and generate new ideas, and helps you work well with others. Intrinsic motivation inspires you to keep learning, to be better, and engage in the team and what we do. This quality is very much needed in the workplace, especially during the pandemic when employees are self-managing to a certain degree. Communication skills are imperative for those who work in a team environment; this also includes being a good listener. Last but not least: adaptability. In an era where things change quickly, employees need to evolve and adapt, including having T-shaped skill sets and a willingness to learn. These character traits are qualities of a good leader and team player.

 

 

Jason Cusack
Senior iOS Developer

 

Why did you first apply to join your company, and how has your experience changed over time?

CoinFlip attracted me initially because of my interest in the fintech industry, and the opportunity was in the right place at the right time. When quarantine began, I spent some time watching conversations on GitHub become ideas and ideas become crypto projects. Behind each of those projects were minds I deeply respected, building products with real use cases. If you’re anything like me, you can only watch liquidity move around for so long before you become compelled to join in, so applying to CoinFlip was an opportunity to merge my personal interests with my career.

Becoming a part of the CoinFlip family was a dream come true, and I spent my first few weeks learning the tech stack and planning out how best to expand the role. What I learned quickly was that everyone in crypto is experiencing enormous growth, and the tech changes rapidly with the needs of the day. My role is less about applying what I already know and more about maintaining the culture of learning and adaptation in an infinite loop. Everything about CoinFlip is exciting! The young energy and optimism here is undeniable.

My role is less about applying what I already know and more about maintaining the culture of learning and adaptation in an infinite loop.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

We’re looking for people who can trust their technical experiences and look forward to growth, learning and adaptation. I hope you put in the time to memorize that efficient Java sorting algorithm, because you’ll be needing that skill set in your day-to-day. Be sure, though, to also show me your deep interest in SwiftUI or Jetpack Compose.

Are you enthusiastic about how Solana differs from Zilliqa? Do you see them co-existing? Is Monero more secure than Dash? If you’re excited about the platforms, we’re excited about connecting with you!

 

 

Cat Zhang
Senior Territory Account Executive

 

Why did you first apply to join your company, and how has your experience changed over time?

I applied to Tock because I love restaurants and wanted experience working at a fast-growing startup with a strong culture. I joined as a member of the sales team two years ago. Over these past two years, Tock has delivered tremendous sales growth and I have learned so much. I have worked my way up to a senior territory account executive role and now have a hand in managing the entire sales process from lead generation to contract negotiation. I’ve developed skills in communication, professional networking and strategic planning. It’s empowering to bring on new customers, because Tock is a product that I truly believe in. We’re helping restaurants by giving them the tools that they need to succeed. 

I love the culture at Tock. Our core values truly reflect in our culture and vice versa. All of us Tockers are driven to excel, passionate about our work and ready to celebrate our wins. Coworkers often join Tock because of the professional and development opportunities, but stay because of the culture and community we serve. I’m a member of Tock’s diversity and inclusion board where I’m able to work with a cross-functional team to create rewarding programs for my coworkers.

Coworkers often join Tock because of the professional and development opportunities, but stay because of the culture and community we serve.”

 

What’s your most interesting or exciting work-related challenge right now, and how are you overcoming it?

We’re growing rapidly with restaurants, bars and wineries all around the world. Our goal at Tock is to help our customers simplify operations, boost revenue, reduce costs and find new ways to delight more guests with their amazing experiences. But the pandemic has been very difficult for the hospitality industry. Restaurants are still facing challenges  and are completely understaffed. This has been a difficult, but rewarding challenge. I have had to become better at building out my territory pipeline of prospects, improve my listening skills and increase my product expertise in order to adjust how I can help each prospective customer I talk with — each with their own unique situations and needs. In doing so, I have been able to exceed my sales revenue goals and overall business objectives.

 

 

Erin Mohideen
People & Culture Lead

 

Why did you first apply to join your company, and how has your experience changed over time?

Inspirant Group is a company that actually puts people first — they don’t just say they put people first — and this was the most attractive thing about the company when I realized I needed a change almost two years ago. 

I applied to join Inspirant during a very pivotal time in my personal life. Suddenly flexibility and the ability to work remotely were incredibly high priorities for me. Inspirant offers these things with no strings attached. I had many conversations with our CEO, Meg Newhouse, and during one I asked her about Inspirant’s take on work-life balance. She said, “Erin, I think that phrase is misguided. There is no work-life balance at Inspirant Group, there’s life balance. Work is part of life, but it’s definitely not the only part of life. To be happy and well-rounded, you create the best balance for yourself.” In that moment I knew Inspirant was where I was meant to be, and I’ve never looked back!

Our values are the foundation for all we do at Inspirant, and if we don’t have people who believe in them, we’re not setting ourselves up for success.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

Inspirant is a small company, and therefore culture is incredibly important to us. When we screen our candidates, we try to determine if they are a culture fit above all else. Work qualifications and experiences come second every time. Specifically, we want to get a sense of whether candidates embody our three core values: having integrity, caring for the greater good and getting it done. Our values are the foundation for all we do at Inspirant, and if we don’t have people who believe in them, we’re not setting ourselves up for success. It’s as simple as that.

 

 

Alyssa Kramer
Director, Technology Applications & M&A Integrations

 

Why did you first apply to join your company, and how has your experience changed over time?

I applied at Green Thumb when I saw a job posting for a position that felt like it was tailor-made for me! I was familiar with Green Thumb and recognized that their brands were often brought up as one of the gold standards in the cannabis industry. 

I’ve learned that everyone in the industry is facing similar struggles, no matter how big or how small the company. Green Thumb handles and overcomes challenges without breaking stride. There are so many areas of difficult terrain, especially around software and regulatory limitations, but we are finding a way to grow in all senses of the word. This is a wild industry, but we’re making great strides, and it’s awesome to be at the forefront with a company like Green Thumb.

There are so many areas of difficult terrain, but we are finding a way to grow in all senses of the word.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

The most important characteristic for candidates in any company in the industry is the willingness to dive in and figure things out and to work with uncertainty. We must be able to respond when priorities shift, regulations change or societal norms lock down or open again. To do that, we embrace and accept uncertainty. For everything we know and everything we plan for, there is still more we do not know. We use the expertise of the people around us to make the best plans and decisions we can. It can be a little scary and overwhelming at first, but when you get through it, it turns out to be really fun!

 

 

Tess Hartigan
Director of Product

 

Why did you first apply to join your company, and how has your experience changed over time?

Belvedere Trading initially stood out to me during on-campus recruiting because it exists at the intersection of finance and technology. I had interned at a tech startup in the Bay Area and knew I wanted to pursue a path in product development. As a proprietary market-making firm, BT builds all of its software in-house as different groups of traders, technologists and product managers collaborate to build cutting-edge trading systems. I had hoped to enter finance while honing my product management skills, and Belvedere offered the opportunity to fuse both industries.

I joined Belvedere just over nine years ago and have seen the firm enact sweeping changes to scale and capitalize on market events. The firm almost doubled in size, greatly enhanced its internal education program, opened new products and strategies, and rapidly innovated its tech stack. One of my favorite changes has been consistent quarterly firm meetings on what Belvedere’s vision is — both short-term and long-term — and our progress toward those goals. Transparency on where we are and where we’re going motivates me and gives the firm collective insight into our direction.

I had hoped to enter finance while honing my product management skills, and Belvedere offered the opportunity to fuse both industries.”

 

When you’re looking to grow your team, what’s a quality that you look for in candidates, and why is it important at your company?

One of the unique parts of the product group is our variety of majors and prior experiences. Our project managers studied everything from computer science and biomechanical engineering to art and economics. When recruiting for product analyst positions, we look for candidates who are deeply interested in building great products and learning about trading. While no prior finance experience is needed, candidates should be excited and eager to dive into this fast-paced industry. We look for intellectually curious individuals who want to flex skill sets in problem solving, data analysis, feature evangelization, facilitative leadership and strategic planning in their everyday work. Candidates must balance digging in individually with team collaboration. 

When asked about a typical day in product, my honest answer is that every day is different — rolling out a new functionality to traders, working closely with end users to improve engagement, planning for the next major global economic event, shaping the vision with a firm stakeholder or presenting key performance indicators. Product is a close-knit group committed to driving innovation forward, and we hope you’ll reach out to us.

 

 

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