Breaking into the retail IT channel takes many forms – some enter through a career shift, others by chance, and some through family legacy. The RSPA asked select members of the RSPA NextGen Rising Stars to share their unique paths into our industry, the key skills needed for success, and the lessons learned along the way. Sharing their perspectives are:
- James Sanders, Cash Register Sales (CRS)
- Crystal Barrineau, OrderCounter POS
- David Sohn, Helpt
How did you get into the retail IT industry?
Sanders: CRS has been a family-run business since my late grandfather, Ken Sanders (H.O. Whistler Award recipient), purchased the company in 1961. As a child, I remember programming Electronic Cash Registers when my father, Dave Sanders (2016 RSPA Hall of Fame inductee), brought home ECRs (electronic cash registers) he was developing at the time.
My journey into the business began with summer breaks during school, working in the warehouse department unloading shipping containers and picking, packing, and shipping products to customers. After college, I transitioned to working full-time at CRS in direct sales, providing POS solutions to merchants in the Twin Cities (Minneapolis-St. Paul, MN) market.
Barrineau: I was roped in when OrderCounter needed a logo — this was before my university even offered graphic design as a major. One logo turned into branding, then gift card designs, then UI work. Before I knew it, I was deep into retail IT well before graduation.
Sohn: A peer suggested looking into the retail IT space. Coming from a vendor that sold hardware into the channel, he recognized the alignment with what Helpt does and recommended that we get involved. Our focus had previously been on IT as it related to MSPs servicing SMBs, and while the retail tech channel is tangential, it is also very closely related.
Can you name a few skills that are necessary to break into retail IT?
Barrineau: Playful curiosity is a must — treat it like a game where every obstacle is just another puzzle. Resilience and adaptability come next. You’ve got to be willing to experiment, fail, and try again. It’s a lot like sketching people in cafes — sometimes the lines don’t make sense until you see the full picture.
Sohn: Persistence to follow paths that will allow you to interact with the right people and connections, and empathy to understand their perspective and needs with a goal to help.
Sanders: Beyond technical expertise, I believe soft skills are crucial, regardless of your role. You need to feel comfortable talking to people, building connections, understanding their needs, empathizing with them, and maintaining a service-oriented mindset focused on helping others.
How do you stay informed about emerging trends and technologies in retail IT? (specific blogs, podcasts, or thought leaders)
Barrineau: I stay curious with a holistic perspective. I listen to industry podcasts like RSPA’s Trusted Advisor and BlueStar’s TEConnect, but the real gold comes from casual conversations at events. Some of the best ideas are in the margins. I also look outside the industry such as comedy show. A good storyteller knows how to keep an audience engaged no matter the topic.
Sohn: I stay informed through RSPA emails (newsletter, industry reports, etc.), as well as by engaging with industry content on LinkedIn and attending key industry events.
Sanders: I actively participate in and consume as much information as possible from North America’s largest community of retail IT VARs, ISVs, and vendors – RSPA! Additionally, I attend industry trade shows to monitor emerging trends and technologies, ensuring I stay up to date with the latest advancements. Engaging with vendors, partners, coworkers, and customers allows me to gain valuable insights into market development, while subscribing to various industry blogs helps me stay informed on key topics and innovations.
Can you share a time when learning a new concept or technology reshaped how you approached your work?
Sohn: There is this new thing, you may have heard of it, AI! It has and will continue to reshape how I approach work. With my focus on customer experience, the ability for AI to ingest a whole bunch of interactions and data and summarize or even apply sentiment to it means that we can be more focused in our upskilling and improve the overall experience.
Barrineau: I fought Canva at first. As a trained designer, it felt like using a toy hammer when you own a toolbox. But once I got the hang of it, I was flying through designs. Same with AI — it’s a fantastic starting point, but the real magic happens when you know how to think creatively. Tools are just tools, but the vision is yours!
Sanders: During my time in direct sales of POS systems to merchants, the rise of the SaaS model fundamentally reshaped how we delivered solutions. Transitioning from a Sell/Break/Fix model to as-a-service required us to implement new financial systems and sales processes. We learned a lot about SaaS through RSPA and fellow members, which helped us adapt to this significant shift in the industry.
What’s the most important lesson you’ve learned in your career so far?
Sohn: Communication is key. It’s easy to make assumptions, and sometimes pride prevents us from asking the necessary questions to bridge gaps in understanding. The ability to challenge these barriers and create an environment where all parties feel comfortable asking the right questions, minimizing assumptions, is incredibly important.
Sanders: Remembering to always practice The Golden Rule: Treat others the way you want to be treated. Solve problems as soon as possible and prioritize relationships over transactions.
Barrineau: Move like water. In martial arts, the most flexible fighters win, and the same goes for creativity. I’ve learned to stay playful, fluid, and experimental — like a science experiment with no wrong answers. It keeps the creativity alive, just like sketching scenes in cafe. If it works, great. If not, move on.
RSPA and its members continue to collaborate and find ways to recruit and build the next generation of leaders. A prime example is best practice sharing that takes place in the RSPA Community meetings. The RSPA NextGen Community meets several times each year to provide a support network and resources for future generations and their companies to advance in the retail technology industry. If you would like to get involved in the NextGen Community, please email RSPA VP of Education Kathy Meader at KMeader@GoRSPA.org.
About RSPA NextGen Rising Stars
RSPA NextGen Rising Stars acknowledges the contributions of young professionals who exemplify the industry’s next generation of channel leaders. Each Rising Star possesses expertise, innovation, and leadership skills that has propelled them to the forefront of the industry, inspiring their peers and colleagues. The RSPA is proud to recognize and showcase these Rising Stars online year-round and in person at our RetailNOW trade show and conference. Meet the 2024-25 RSPA NextGen 50 Under 40 Rising Stars on this webpage.
About RSPA NextGen Community
The RSPA NextGen Community works to identify and develop opportunities for future leaders and the rapidly changing technology landscape. Joining this community allows you to meet others who share passion for retail technology and provides a forum to share ideas on how the industry, and the RSPA, should move into the future. The NextGen Community hosts virtual discussions throughout the year and meets in person at RSPA’s signature conference RetailNOW. Learn more about the RSPA NextGen Community on this webpage.
