“5 Things You Need To Know To Create a Successful App or SAAS”, with Jeremy Baker of Retail Zipline

Mitch Russo
Dec 11, 2019 · 12 min read

Never forget that it’s all about the people. We exist to enable positive change in our customer’s lives, not to build a product or a company. The work is second to the impact.

I had the pleasure of interviewing Jeremy Baker. Jeremy is the co-founder and current CTO of Retail Zipline, a company that was built to help streamline and coordinate retail communications. He is a seasoned developer and entrepreneur who has been involved in web design, online product development, and technology startups since 1997. Prior to Zipline, Jeremy co-founded MightyHive, an enterprise software startup acquired by S4 Capital for $150M. Before that, he worked as a Senior Prototyper at Yahoo! for nearly five years.


Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve been involved in web design, online product development, and technology startups since 1997. I taught myself to code in high school and then decided to build a web design company instead of going to University. I’ve been working in the industry ever since. I didn’t even get to drop out like all the cool kids.

I built web software for companies all over the world before landing at Yahoo, where I spent 5 years on their search and internationalization teams. That’s where I met my co-founders for MightyHive, the enterprise ad-tech company that was acquired by S4 Capital last year for $150M.

All of the things I learned in the many different roles I had set me up to be very prepared when I had the fortune of meeting Melissa and learning about an untapped opportunity in retail software.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

It was actually a baby shower that made it all happen. Melissa, just an acquaintance at the time, hosted the baby shower for my first child and used that opportunity to pitch me on the idea of a better retail communication product.

I didn’t know much about the inner workings of retail at the time but Melissa’s passion and frustration was hard to ignore. In order to better understand the problem on my own, one of the things I did was walk up Market Street and go into each store to ask questions. It was immediately obvious how little support they had and how behind their technology was. The lack of clear communication made it impossible for them to keep up with the rapid changes that were happening in retail. You could feel the frustration in every conversation.

My time at Yahoo! and MightyHive had taught me a lot about the value of rapid changes and testing new ideas. With retail being a 4.4 trillion dollar industry, it was abundantly clear that better tools for the people at the front lines could unlock millions of dollars in lost profits.

Building a product that reduces frustration in an industry that’s been left behind to unlock millions of dollars in value? That’s exactly the type of company I wanted to help build.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

In the span of 7 years, my wife and I have raised two kids, lived in 3 cities, and founded two successful high-growth startups. Anyone who has started a company or had a kid knows that it’s hard. Combining all of that at the same time? Yeah, there were many moments where I felt like we should quit.

People talk all the time about the near-death moments, and Retail Zipline had enough of those in the early days. But really, those are just problems to solve. They aren’t the hard part for me. The hard part is pushing forward every single day. One foot after the other, no matter what.

To this day, I’ve never found a magic bullet or secret that makes it all easy. It’s just hard, straight up. In the early days of Retail Zipline we moved our family back to Canada because health insurance for founders in the US is too expensive and we wanted to be near family. My wife and I moved to an 800 square foot apartment with two kids under 3. I was working quietly in the dark until 1 or 2 in the morning, crashing on the couch, and then waking up at 6am with the kids for months on end.

Where does the drive come from? That’s easy. Friends of ours gave us money and believed in us. My wife trusted me with our future. Employees trusted us with their careers. Our customers trusted us with their business. My co-founder trusted me with her idea and it still made sense. You don’t quit. Period.

So, how are things going today?

I am stunned every day at what we’ve built in such a short amount of time. Our company provides communication software to many of the world’s best retail brands. We truly have amazing customers who partner with us every day to help support store teams.

I’m happy to say that I’m no longer working in the dark and sleeping on the couch. I’ve left the Bay Area and lead our 100% distributed team from a nice house in the suburbs of Kansas City away from the chaos. Our team is made up of kind, talented people from all over the world and we’re truly doing our best work.

Our business is booming. In May of this year, we raised Series A funding from Emergence and Serena Williams through her venture firm, Serena Ventures. We’re so proud and humbled by their support, and are especially excited that we were Serena’s first investment in a retail SaaS product. She’s passionate about improving the lives of the underserved, and in this case, she believes in our mission to help everyday people working in retail.

We continue to expand our team and we’re thrilled to welcome Tom Burke, who hails from Bain + Co and McKinsey, as our new CFO, and Randy Ray, who brings years of experience at Oracle, IBM and Accenture, as our new VP of Sales.

There remains a lot of work to do and we have a long way to go, but I am excited and thankful every day that I get to do this work with this group of people.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

We had taken Retail Zipline through the Alchemist Accelerator and Melissa did an amazing job on demo day. Her presentation was a hit and we had a lot of outreach from VCs. But, we’d made a mistake. In a last minute decision, we swapped out the desktop screenshots of our product for mobile screenshots. We’d also included a video of major retailers that we’d interviewed talking about the problem on our behalf. It wasn’t clear what stage of the business we were in.

When we met with VCs, they were expecting to see an established company with a beautiful mobile app and major enterprise customers. Instead, it was just the two of us with no finished product, no employees, and no customers. The looks on their faces were priceless.

Combine that with the “Retail Apocalypse” and very few people were interested in investing. After 3 months of pitching, the few large cheques that we did get offered had horrible terms or were from people with no alignment in what we were doing.

We had to make a tough call. Keep pitching, give up, or buckle down on what little money we had and figure out how to make it work. We buckled down, spent very frugally, found amazing customers, started generating revenue, and waited for the right investors. It ended up being exactly the right decision, but we wouldn’t have known it at the time.

What do you think makes your company stand out? Can you share a story?

I think the way that we care about people makes a huge difference and permeates every decision that we make. People truly matter in our company and that’s reflected equally in the way that we treat customers, competitors, and employees.

Like many enterprise software sales cycles, the person who buys your product isn’t the person who uses our product. Many companies fall into the trap of listening to the HQ buyer and ignoring the users because they don’t make the buying decision. We’ve had big money waved in front of us to build a feature, but we’re not doing this for the money. That doesn’t align with our goal of improving the lives of retail employees.

We truly care about what their experience is and we put the time in to make sure that we’re meeting their needs. Our customers love us for this because ultimately we should all be aligned on the same goal; make store teams happier and more effective.

Case in point, Brandon Panepinto from Gap Inc was on stage with me at the National Retail Federation’s Big Show a few years back. He said “You guys understand our store teams as well as we do — sometimes a little better.” That’s what we’re going for, and I think that makes us a very different company in our space.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I’m probably not a great source of information for this one. I’ve burnt out a number of times. When you’re pushing yourself hard in an intense situation with a lot of challenges it’s bound to happen. Startups don’t always give you the space you need to recover; sometimes it really is make or break and you have to push through.

I think fear of admitting that you’re burnt out is probably more damaging than burnout itself. People talk about it like it’s the end. You’re done. Kaput. But that’s not true at all. It’s a temporary state. I think better advice I can give is probably how to recover from burnout.

Burnout comes in the form of just not being able to focus for days on end because you get overwhelmed and can’t find your way through. Sometimes it’s just due to exhaustion and you need to get some good sleep. Other times it truly is too much for one person to handle even at their peak and you need to chart a path through.

Spend a few days admitting that you’re burnt out and doing just one thing per day that has an impact. Then, when you’re ready, my favorite technique to deal with it is to follow the Getting Things Done approach to doing a Brain Dump. Grab a piece of paper and write down EVERYTHING that you can think of that you’re responsible for. Get it all down. Personal, professional, whatever.

I find the act of getting it all out to be therapeutic. It helps you not worry that you’re forgetting about something because it’s written down.

Then, assign the three Ds. Do, Delegate, Delete.

Do: These are things that must be done and ONLY you can do. No one else in the world could do them.

Delegate: These are things that must be done and someone else can do.

Delete: These things are important but don’t have to be done.

Then, start small by doing the next thing on the Do list and moving forward. I always find myself back up and running in no time at all with a clear head and a plan of action.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I’ve had the pleasure of working with a lot of great people who have taught me many things and opened up doors that were otherwise not available. But, ultimately, it’s the women in my life that deserve the most gratitude.

My mother taught me resiliency, courage, confidence, and resourcefulness. She always found a way to make things work out and found the moments of joy in every situation. The older I become the more I recognize just how fortunate I am to have her in my life.

My wife is my partner through thick and thin. She believes in me, covers for me, and runs our life so that I can focus on the work that has made everything possible. It’s incredibly powerful to have someone you trust taking care of the other important things in life.

And last but definitely not least, my co-founder Melissa. She understands the pain-points retail employees face and how to solve them better than anyone else. She is deeply passionate about improving the lives of retail employees and has a clear vision for how to do that. Most importantly, she exercises patience and grit. Founding a successful company is a long, bumpy road and you need to be able to weather storms together.

How many users or subscribers does your software currently have? Can you share with our readers steps you’ve taken to build such a large community?

Over 170,000 retail employees use our software, but that’s growing every day as we push towards our goal of improving the work life of 2 million retail employees by 2025.

There’s no big secret to our growth, we’ve just been maniacally focused on building the most effective and easiest to adopt retail communications product in the world. This has caused our customers to really take notice, and most of our growth is through word of mouth from one retailer to the next. We have almost a cult like following, which is really strange to say about enterprise software, but it’s true.

What is your monetization model? Have you considered other monetization options? Why did you not use those?

We charge a flat rate per store and we chose that model very deliberately. Many products charge per user, and that would probably allow us to charge our customers more money. But, that pricing model causes the retailer to choose which users get access and creates unnecessary barriers.

When it comes to communication, you want everyone to be on the same page. Pricing that allows everyone to use the product is critical.

Based on your experience and success, what are the five most important things one should know before one wants to start an app or a SAAS?

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

I grew up in a small town in Canada and my mom worked at the local community center. Through her experience I had the opportunity to see the value of community in bridging gaps and helping people through hard times. Strong communities thrive through change while weak communities struggle and often fall apart. I think we’re seeing that with the opiate crisis and the changing labor opportunities in North America.

I’m a big fan of the work of John F. Helliwell, the Canadian economist and editor of the World Happiness Report. In his studies, he found that when people find a place to belong, trust others, socialize more, and are able to be generous they are happier in life.

The movement I would start would be a framework to help people build stronger communities in their local towns and neighborhoods, which I think would give people strength through change and provide more opportunity to reach those four guidelines of happiness.

Of course, tying this back to Retail Zipline, physical retail stores are a huge component of community and socialization that I think are worth supporting and preserving. A sub goal that I have with this company is to give retail stores the opportunity to create amazing local experiences for every community that they’re in.

How can our readers follow you on social media?

https://twitter.com/jhubert

https://linkedin.com/in/jhubert

Thanks for all of these great insights!

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Mitch Russo

Written by

Author of The Invisible Organization — How Ingenious CEOs are Creating Thriving, Virtual Companies & Power Tribes — How Certification Can Explode Your Business

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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