Jordan Boesch, 7shifts: Six Years as a Side Project Before Full-Time Focus

1Mby1M Research · 1Mby1M Case Study

Interviewer: Sramana Mitra

This interview is part of the case study-based research and entrepreneurship education work of 1Mby1M, the global virtual accelerator founded by Sramana Mitra.

Abstract

Jordan Boesch 7shifts CEO built 7shifts, a team-management platform, initially as a solo side project for his father’s Quiznos locations while working full-time as a software developer. Over roughly six years, from 2007 to 2013, he bootstrapped the tool from a simple Excel-sharing portal into a paid product with a broad but unfocused customer base. He worked on the product incrementally, often only an hour at a time, learned directly from early users, and reached approximately $40,000 in ARR – enough to support himself – before leaving employment to work on 7shifts full-time.

This early period reflects the Bootstrap First, Raise Money Later by Solo Founders methodology. Before taking outside capital, Boesch independently built and tested the product, acquired customers organically through online search, experimented with a simple per-employee pricing model, and established real recurring revenue. The company did not begin with a large team, a polished pitch, or institutional funding; it began with firsthand customer insight, a functional solution, and six years of gradual validation.

A 2014 tech accelerator, which provided $150,000 in funding, prompted a pivotal repositioning: Boesch and his co-founders deliberately narrowed the product to focus exclusively on restaurants, despite two-thirds of existing customers coming from other industries, and relocated the company back to Saskatchewan to keep costs low. That focus, combined with SEO-driven content marketing and integration partnerships with restaurant point-of-sale platforms such as Toast, drove revenue from $40,000 in 2013 to $1 million by 2016. Only after establishing this stronger product-market fit and meaningful revenue did the company raise its first institutional seed round.

Subsequent rounds – including a $3.5 million raise, a Series A with Napier Park, a Series B with EHI, and an $80 million round from SoftBank in 2022 – fueled growth to a scale serving one in 25 restaurant workers in the United States.

This case illustrates how Bootstrap First, Raise Money Later by Solo Founders can create a durable foundation for growth. Boesch’s years of self-directed product development, organic customer acquisition, and capital-efficient execution allowed 7shifts to approach investors with proof of demand, revenue, and a focused market strategy, reflecting the 1Mby1M principle of validating the business before using outside capital to accelerate it.

Transcript of the Interview

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, and raised, and in what kind of background?

Jordan Boesch: I’m from Saskatchewan, a province in Canada. I’m the CEO at 7shifts which is a team management platform. Before 7shifts, I was a software developer for many years. I ended up working for my dad who ran some Quiznos locations.

It was there that I saw some of these challenges around managing teams – scheduling and communication being a core aspect. That’s what spurred my interest in taking some of the things I had learned about building websites to try and build something to help my dad.

Sramana Mitra: Where did you do software programming? Did you just self-learn?

Jordan Boesch: I was big into gaming. I was building websites for the teams that I was gaming for. That was an entry point into what spurred my interest in building apps and software. I ended up going east to Ottawa to take a multimedia development diploma. Part of that diploma was classes in coding.

I didn’t have the grades to get into university, so I took a diploma program in college. It spans the gamut of audio and video editing, design, and programming. After that was finished, and even during, I was already consulting and working on the side. I ended up taking a job in the field after that diploma program was over.

Sramana Mitra: What years are we talking?

Jordan Boesch: This was 2007.

Sramana Mitra: How long did you do this mode of software development work working for other people as a developer before starting 7shifts?

Jordan Boesch: 7shifts was in tandem with this. It was just a fun side project to help my dad with scheduling at his restaurant. It was something that I had opened up to the online world to sign up and pay with PayPal. I had all that going on and some trickling clients here and there while I was doing some consulting. It wasn’t until 2013 when that scale tipped so hard onto one side that I was able to do 7shifts full-time.

Sramana Mitra: Between 2007 and 2013 while 7shifts is going in parallel, what was the product?

Jordan Boesch: It was really just a portal where employees and managers could log in to build schedules and employees could log in to check their schedules. It started out initially as the ability for my dad to just upload an Excel spreadsheet and staff would share the exact username and password and download that spreadsheet. It was very basic.

In that time between 2008 and 2013, it was something I worked on for an hour here and there because I enjoyed building things. Everything I learned, I would take that and build more into 7shifts. It was a fun learning exercise.

Sramana Mitra: Beyond your dad, how did other customers find you?

Jordan Boesch: We had it online and people were finding us because they were just looking for scheduling software. They would google us and they’d sign up. I didn’t think anything about how to expand and get more. It was really just a fun project for me where folks could sign up and I could talk to them and learn about their needs. That’s how people found us.

Sramana Mitra: How much were they paying?

Jordan Boesch: At that time, we charged per employee, which is different than how we charge now, which is by restaurant location. I think we charged a dollar per employee per month.

Sramana Mitra: You positioned as a restaurant scheduling software?

Jordan Boesch: Before we positioned it for restaurants, we were trying to be everything to everyone. There was a turning point where that changed. Although it was developed with my dad in mind, it took on a life of its own where we had various industries signing up – everything from retail, medical professionals, and staffing agencies. You name it. They were there. We didn’t think much of it at that time. We did go through an inflection point where that changed.

Sramana Mitra: When did that come?

Jordan Boesch: We took part in a tech accelerator. We raised $150,000 after that. That was in 2014. We decided that we don’t want to build a product that feels like it was okay. We want it to evoke an emotion that people feel like this is the best product in the market.

We said in 2014, “We’re just going to go after restaurants.” It was scary. Two-thirds of our customers were non-restaurant customers. We made this massive change. If you were a medical company, suddenly you were seeing pictures of restaurants on our website. We did lose some customers at that time. We were very determined that the restaurant industry needed a product like this.

A lot of the reason we got early on as to why people didn’t focus on the restaurant industry is that they’ve all said that margins are low and restaurant operators will never pay for anything. When we heard that, it sounded like an immense opportunity. Restaurants are going to be around for a long time, if not forever.

Sramana Mitra: A sharper positioning took place in 2014.

Jordan Boesch: Yes.

Sramana Mitra: You said you started this by yourself. By the time you did the accelerator, you had co-founders. How long did you do this by yourself before the other two people got on?

Jordan Boesch: Full time, I only did it by myself for a few months, but I was working on it for many years as a side project. I thought that it’s not as exciting to work by yourself. I wanted to work with a team again. I get a lot of energy from working with great people.

Sramana Mitra: Until 2013, you were working mostly by yourself.

Jordan Boesch: Right.

Sramana Mitra: What was the revenue level before the accelerator?

Jordan Boesch: It was about $40,000 ARR. That was just enough for me to live. That was when I had that shift of leaving my job as a software developer at another company.

Sramana Mitra: Then you bring in this $150,000 funding after the accelerator. Where did you put in that money to scale?

Jordan Boesch: We put it into just hiring more people to build the product. We hired about three software developers. $150,000 in the Bay Area wouldn’t last us very long.

Sramana Mitra: You were in the Bay Area?

Jordan Boesch: When we were part of the accelerator. That $150,000 just wouldn’t have lasted us very long. We took it back home and converted it into 220,000 CAD. We were able to hire a few people with that and focus on building a product.

Sramana Mitra: Were your other co-founders technical?

Jordan Boesch: My wife is not technical. She was doing client success, sales, and business development. I was doing design and web development. Our third co-founder was doing the mobile apps.

Sramana Mitra: How did you find him?

Jordan Boesch: We were connected through a mutual friend earlier on. The province that we’re in is only a million people. Naturally, the development community is pretty small, so we knew each other from events.

Sramana Mitra: That’s wonderful! I love stories from small communities.

Jordan Boesch: When we raised $150,000 and brought it back to Canada, people thought we were stupid for leaving the tech ecosystem of the world.

Sramana Mitra: You want to keep your cost down as a startup. If you’re acquiring customers from all over the world via digital marketing means, it doesn’t matter where you are located. That’s how off-center geographies are building world-class companies these days.

Jordan Boesch: There are pros and cons. The cons were clear that there’s not as much senior talent. It’s not like we were moving to Toronto or Vancouver. We moved back to Saskatchewan. At that time, I could count on my hand how many software companies were in the city.

It was a big move for us. We were very determined that we wanted to be part of building and shaping the tech ecosystem where we’re from. We thought we could take so many great learnings and bring it back to our community and help grow it. I like being part of that pioneering journey.

Sramana Mitra: This new product development effort that you were putting in, did that also result in you changing business models? What was the impact?

Jordan Boesch: It was for building more features. It was all for R&D. We didn’t change prices a whole lot. We were more focused on just building a sticky product.

Sramana Mitra: It was still a dollar per employee per month.

Jordan Boesch: Yes. We just invested in building additional features. We also used it to integrate it with restaurant-focused POS. That was what helped catapult us into restaurants. Our product wasn’t quite there yet for restaurants. It took years to build some of the functions that we felt were important and unique.

What actually pulled us into the segment more was the partnerships. It was establishing great partnerships that integrated with other restaurant technology. That gave us more customers in the restaurant space. That also gave us more feedback.

Sramana Mitra: What was the first platform partner that you went for?

Jordan Boesch: The first one was Toast.

Sramana Mitra: Toast has a marketplace, right?

Jordan Boesch: Right. That was very important in the early days.

Sramana Mitra: The marketplace was generating a lot of leads for you?

Jordan Boesch: It was generating some. What was interesting is, as these cloud POSs raised money and converted more restaurant customers to the platform, these customers started seeking out other software that integrated with the product they just bought. There was this new persona of a restaurant type of person that was looking for software now. We were in the marketplace. For other customers that were more interested in cloud POS and cloud products, we also saw a lot of those too.

Sramana Mitra: In terms of marketing and customer acquisition, was Google search still yielding for you?

Jordan Boesch: Yes. If you searched for something as basic as restaurant scheduling software, there’d be no organic relevant results. We thought this was a great opportunity to build content around these keywords. We didn’t have a ton of money to spend on Adwords. We were very careful about that.

What we did do is we built a lot of content around restaurant scheduling software. That was so important for us to establish ourselves as the number one ranking organic result, which I still think exists today.

Sramana Mitra: What percentage was coming from that pure Google search around your content?

Jordan Boesch: I don’t remember exactly. Probably almost all of it.

Sramana Mitra: That’s a very good place to be. How did the revenue ramp up in 2015?

Jordan Boesch: We were growing at a decent clip. In 2013, we were $40,000 in ARR. In 2016, we were a million dollars. We went from $40,000 to a couple hundred, to $500,000 to a million. At that point when we had a million in ARR, we closed a million-dollar seed round with our first institutional investor.

Sramana Mitra: This is in 2016?

Jordan Boesch: Yes, exactly.

Sramana Mitra: Where did you raise money?

Jordan Boesch: This VC straddles both Canada and Bay Area. I was meeting with their partner who’s in Toronto. I was flying to Toronto many times a month to update them and pitch. I still like that part of it. A lot of people don’t like pitching to investors. I love telling that story. What was great is behind that story was a lot of real tangible revenue growth as well.

Sramana Mitra: Absolutely. So $1 million in revenue and a million in financing. What happens next?

Jordan Boesch: We hired more software developers. We hired a designer. We hired our first person that had kids in the family. You’re now on the hook for someone’s family. We hired the team, built the product, and then raised $3.5 million a couple of years later. We kept building the team.

When we were raising $3.5 million, it was around that time when a lot of founders go through this uncertainty. If you don’t raise, what happens to the business? Am I doing the right things? Am I right for the role? We aligned with some investors and closed. Our confidence rejuvenated and went back at it. We’re working with some larger customers.

Sramana Mitra: These larger customers were finding you?

Jordan Boesch: A lot of them were. A lot of them we weren’t ready for yet. One of the mistakes is, instead of saying we’re not ready, we could have built stuff for them. If I could go back, being true to your core audience is so important. A lot of founders think that there’s something way out there that they’re not seeing that is this magical growth lever.

I think it’s been shown to me that, more often than not, it’s right in front of you. It’s just more of what you’re doing. It’s doing it better. It’s one foot after the other. You got to crawl. You got to walk. You got to run. You think there’s something else you’re missing and it’s out there. You take your eye off the engine you’ve built that’s producing. Now that core foundation starts to diminish because it’s losing your attention. Focusing on that and augmenting that is really important.

Sramana Mitra: Did you just do more of the same for the next few years?

Jordan Boesch: Yes. There were some interesting moments. We hit about 30 people. You start to feel these inflection points where things start to get rocky. It’s a lack of process for things. As a startup, you thrive off of not having processes.

As we grew, I could feel that starting to happen at 30 people. We brought in a consultant to help us in putting in some lightweight frameworks to help guide the business. That was helpful for us. When we hit 50 people, we had almost a full-time facilitator that was part of our team that was doing planning with us and helping with some lightweight frameworks.

We are now 300 people. We still have this person today. The lightweight things that we have implemented into our process, we call it the 7shifts operating system.

Sramana Mitra: You got to build your own software and processes for your company to operate smoothly. Are the employees in your province?

Jordan Boesch: 80% are in Saskatchewan and Toronto. The other 20% are in Calgary, Vancouver, Montreal, Atlanta, and New York. It’s everywhere now. It’s allowed us to perform at a different level.

Sramana Mitra: Did you raise any more money after that first round in 2016?

Jordan Boesch: Yes, we raised a Series A with Napier Park. They’re really great, experienced company builders. After that, we raised Series B with EHI. Then this year [2022] in January, we closed an $80 million round with Softbank. A quarter of our entire company was added last quarter. It’s been a fun journey.

Sramana Mitra: What revenue level are you at?

Jordan Boesch: What I can say is we’re used by one in 25 restaurant workers in the US today.

Sramana Mitra: From being a hands-on developer to being an entrepreneur, what do you think have been the most important things that you’ve done to make that transition?

Jordan Boesch: I don’t know if it’s necessarily about what I’ve done. I think it’s more important to have certain traits or behaviors. Resilience is really important. Self-awareness is very important. Getting a good understanding of where and how you need to fill those gaps is critical. Also, the ability to make tough calls.

Sramana Mitra: How much did you learn at the accelerator?

Jordan Boesch: We learned a lot about what it takes to build a big company that’s going to drive impact. You’re working around teams that are just working all the time. You leave at midnight and come back at six in the morning. Everyone talks about work-life balance. Running a startup that’s trying to compete on the global stage, that’s not our reality.

Sramana Mitra: Startups don’t offer work-life balance. What I observed in your story is you learned positioning at the accelerator. As part of the accelerator, it seems like you did a pivot to focus on the restaurant segment. Laser-sharp positioning is one of the keys to achieving higher velocity growth. It seems like that’s one of the things that you worked on.

Jordan Boesch: We definitely felt that even when we left. We looked around us. You learn through osmosis through feedback. We were seeing good early signs of success with restaurants. We just didn’t have as many of them as we wanted. The features were almost there. As soon as we made those leaps in doing integrated work with restaurant technology, it started the cycle.

Sramana Mitra: Thank you for your time.

Key Takeaways

• Bootstrap First, Raise Money Later by a Solo Founder: Jordan Boesch started 7shifts as a solo side project in 2007 while working as a software developer and consultant. He built the original scheduling tool for his father’s Quiznos restaurants, developed it gradually in his spare time, and did not rely on outside funding to begin.
• Boesch spent roughly six years independently testing and improving the product before working on 7shifts full-time. The initial tool evolved from a basic portal for sharing Excel schedules into an online product where managers could create schedules and employees could access them. Customers found it organically through Google search and could sign up and pay through PayPal.
• By 2013, 7shifts had reached approximately $40,000 in ARR, which was enough for Boesch to leave his software-development job and focus on the company full-time. This demonstrates the Bootstrap First principle: establish baseline revenue and customer validation before assuming the financial risk of full-time entrepreneurship.
• The company received $150,000 through a tech accelerator in 2014, but the more consequential result was a strategic repositioning. Boesch and his co-founders chose to focus exclusively on the restaurant market even though approximately two-thirds of existing customers came from other industries. The decision created a clearer value proposition and stronger product-market fit.
• The team kept operating costs low by returning to Saskatchewan after the accelerator and using the funding primarily for product development. The capital supported the hiring of a small group of software developers and the creation of restaurant-specific functionality rather than premature spending on broad expansion.
• SEO-driven content marketing around terms such as “restaurant scheduling software” became a major customer-acquisition channel. 7shifts also developed integration partnerships with restaurant point-of-sale platforms, beginning with Toast. These partnerships brought more restaurant customers, deeper product feedback, and stronger positioning within the restaurant-technology ecosystem.
• Revenue increased from approximately $40,000 in ARR in 2013 to $1 million in ARR by 2016. Only at that point – after six years of bootstrapping, a focused vertical strategy, organic acquisition, and demonstrated recurring revenue – did 7shifts raise its first $1 million institutional seed round.
• With the foundation validated, 7shifts then used external capital to accelerate rather than discover its business model. The company later raised a $3.5 million round, a Series A with Napier Park, a Series B with EHI, and an $80 million round from SoftBank in January 2022, growing to approximately 300 employees and serving one in 25 restaurant workers in the United States.