Inside 2 Chicago Tech Companies That Prioritize Professional Development Opportunities 

See how OppFi and TravelPerk put learning and development first for employees. 

Written by Taylor Rose
Published on Aug. 07, 2025
A collage of two people with laptops are sitting on a paper airplane to show the concept of learning to grow your career.
Image: Shutterstock 
Brand Studio Logo
REVIEWED BY
Justine Sullivan | Aug 08, 2025
Summary: OppFi and TravelPerk emphasize career growth, learning culture and tech stack development. OppFi funds conference travel, runs tech book clubs and hackathons, and its developer mentorship has 50+ pairings across four iterations; one employee moved from QA to software engineer in five months. TravelPerk provides Looker training and Udemy courses,... more

Figuring out the next move in your career is one thing, but finding an employer who empowers you to make your next three is a whole other. 

Professional development and upskilling are the key to career growth, especially in a rapidly changing tech space. 

So it’s not surprising that nine in 10 millennials say professional development or career growth opportunities are very important to them in a job, according to a Gallup survey. The same study also found that organizations that invest in employee development are 11 percent more profitable and are twice as likely to retain employees.

Built In found two Chicago tech professionals who were eager to share how professional development impacted their careers. 


 

Brennan Walsh
Manager Engineering • OppFi

OppFi is a leading tech-enabled digital finance platform that works with banks to provide financial products and services for everyday Americans.

 

What new skill or role did you want to learn? Why was this important to you?
When I joined OppFi nine years ago as a loan advocate, I was simultaneously attending a coding bootcamp with the goal of transitioning out of a customer-facing role to a more technical role.

After completing the bootcamp, OppFi offered me the chance to transition to the tech department as a quality assurance engineer, with a clear path to becoming a software engineer. Leaders within my company provided a comprehensive learning journey, including videos, books and projects. Within five months of starting in my new role as a quality assurance engineer, I achieved the role of software engineer.

 

How did your employer help support this time of learning and professional development?
OppFi fosters a culture of professional development and continuous learning where leaders champion investing in our people.

OppFi has sponsored my travel to attend software conferences including RubyConf, Strange Loop, Velocity Conference and Go-To Chicago. These conferences offer exposure to new technologies and networking within the tech community. Internally, the tech department hosts a tech book club and hackathons, allowing employees to explore ambitious projects and experiment with emerging technologies.

Our tech team emphasizes pair programming, which has been a consistent source of real-time learning guided by senior employees. One initiative I’m proud to have implemented is a mentorship program for developers. At this time, the program has run through four iterations and set up over 50 mentorship pairings for developers looking to grow in specific technical domains. OppFi provides free access to online learning via LinkedIn Learning, FranklinCovey and Pluralsight. I’ve taken classes on Ruby on Rails, JavaScript, React, Java, domain driven design and GitHub Copilot, among others. For the new year, I plan on using OppFi’s tuition reimbursement program to get my MBA.

 

What was the outcome of this experience? How did it impact your future growth in your profession?
My nine-year tenure at OppFi has supercharged my career. Over this period, I’ve held approximately eight different titles, each offering a unique opportunity to enhance my skill set.

The impact on my earning potential has been particularly notable. My compensation has increased significantly as my skills and responsibilities have grown.

During my tenure, OppFi has consistently offered numerous learning and advancement opportunities, enabling me to significantly enhance my skills while also significantly improving my overall quality of life. This underscores the value of a supportive environment that fosters skill development and career progression.

A group of TravelPerk employees chat in a group.
Credit: TravelPerk

 

 

Hannah Frentzel
Enterprise Account Manager • TravelPerk

TravelPerk is a hyper-growth SaaS platform offering companies a one-stop-shop for booking, managing and reporting business travel.

 

What new skill or role did you want to learn? Why was this important to you?

In my role as an account manager, I help clients optimize their travel strategies by recommending solutions that save time, money and boost efficiency. I always support these recommendations with data. While I joined TravelPerk with a strong foundational understanding of data, I had limited experience with business intelligence visualization tools like Looker. I was eager to develop my skills in this area and really take my knowledge to the next level so I could better serve my clients.

 

How did your employer help support this time of learning and professional development?
TravelPerk supported my education in many ways. The internal data team offered optional training sessions from beginner to expert levels, which I found incredibly valuable. I also leveraged TravelPerk’s Udemy access to take online courses including those focused on business intelligence. Cross-departmental collaboration is welcomed which made it easy to connect with data team members who were always generous with their time and knowledge. This supportive environment, combined with my manager’s help in balancing my workload, allowed me to start building my own dashboards within weeks.

 

What was the outcome of this experience? How did it impact your future growth in your profession?
My new data skills have led me to build countless complex reports and dashboards that have been critical to my own role and have been widely used by my team. Now, I can rapidly create extremely specific data visualizations for any client request or question, noticeably increasing my credibility. This valuable, specialized skill has directly contributed to my advancement at TravelPerk from mid-market account manager to senior account manager and, ultimately, to enterprise account manager. This expertise has already proven vital in my current role, and I know it will serve me well throughout my career.

Responses have been edited for length and clarity. Images provided by Shutterstock or listed companies.