Our Faces Behind the Breakroom: John Portwood

As we continue our Faces Behind the Breakroom series, we’re taking a closer look into the day-to-day of our sales team members. March is rounding out with John Portwood.

We got to ask John some questions to truly get a better look at his day-to-day and what helps those breakrooms solutions come to reality.

Walk us through a typical day for you.

No two days are ever the same, which is one of the things I love about sales. A typical day usually starts with reviewing emails and checking on active opportunities. From there, I might have client meetings, which are either on-site tastings, equipment consultations, or virtual calls. I spend a good portion of my time prospecting, following up on proposals, and coordinating internally with operations to ensure smooth onboarding for new accounts. Relationship-building is constant throughout the day.

How do you prioritize tasks when juggling multiple deals or clients?

I prioritize based on urgency and impact. Active deals that are close to closing obviously require immediate attention, but I also make sure to nurture longer-term opportunities. Staying organized is key—CRM tools, task lists, and calendar blocking help me keep everything moving without letting details slip through the cracks.

Can you share a recent win and what made it successful?

A recent win for me was working with a client who was a little hesitant to switch suppliers because they were worried about consistency. I didn't rush it. Instead, we set up a personal tasting, sat down together, and I walked them through how we source our products and handle quality control every step of the way. I also made sure they understood how we'd stand behind them for the long haul. In the end, it wasn't just about having a good product. It was about slowing down, listening closely to what was really bothering them, and speaking straight to those concerns. That's what built the trust and got the deal sealed.

Any advice you’d give to someone just starting in sales?

Focus on listening more than talking. Early on, it's tempting to pitch constantly, but the best salespeople ask thoughtful questions and truly understand the client's needs. Also, don't take rejection personally—persistence and consistency win over time.

How do you maintain work-life balance or recharge after a busy week?

I make it a priority to unplug when I can. Spending time with family helps me reset. Sales can be high-energy and fast-paced, so having intentional downtime keeps me sharp and motivated for the week ahead.

If you could have a coffee with any business leader, who would it be and why?

I would select someone from our Five Star management team. We are fortunate to have exceptional leaders who can thoughtfully share our company’s journey—where we began and the direction we are heading. I am truly proud to be part of this team and the meaningful work we are accomplishing together.

What’s the most unusual or surprising thing you’ve learned in your role?

One surprising thing is how much coffee quality influences overall brand perception. A great cup of coffee can elevate a business's reputation in ways many owners underestimate. It's not just a beverage, it's an experience.

As you can see sales reps are not always thinking of “making the sell” and John is an example of making it a priority of slowing down, listening closely, and speaking straight to concerns especially when something involves big changes.

Your team deserves better, and with a rep like John, that’s achievable and approachable. If you or someone you know needs a breakroom refresh or wants to learn more about breaktime solutions, John is just a get started button away.