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Big picture thinking: How Worksimply was able to double down on a new market to serve more customers

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Big picture thinking: How Worksimply was able to double down on a new market to serve more customers

The secret to business growth? Think 10 steps ahead – always.

Thinking about what the future of work looks like? The founder of Worksimply, Jaime Aoyagi, is your guy.

It goes without saying that the future has changed forever and remote work is here to stay. But what most employers may not realize is that the workplace of tomorrow isn’t just confined to an at-home office or central downtown location.

Aoyagi predicts that the future of work will take place in three main spaces: an at-home office, a central headquarters that’s typically located in a downtown core and an on-demand workspace that’s less than a 10-minute commute from the employee’s home.

Catching a new wave of opportunity and recognizing the transformational shift taking place in office settings, Aoyagi decided to grow Worksimply – a workplace platform – by doubling down in a new market to serve more customers.

We sat down with Aoyagi to learn more about Worksimply, and how he was able to shift markets by thinking bigger.

First, can you tell us more about what exactly is Worksimply?

“Worksimply’s solution is two-fold. For hybrid companies, we offer a workplace platform that makes office space more affordable and increases employees’ freedom. For co-working space operators, we offer software to manage end-to-end guest bookings for co-working spaces.

To put it into perspective, we help small businesses manage their own hybrid workforce by allowing their employees to book desks at their HQ and at co-working spaces all across North America,” said Aoyagi.

A cycle of various workspaces - How Worksimply was able to double down on a new market

What do you think is unique about Worksimply’s value proposition?

“Fostering an engaging work culture is crucial to creating a well-oiled, productive and happy team. At Worksimply, we understand how challenging this has been for remote and hybrid teams and are working to help them better manage their remote culture.

While a lot of companies today are working in a predominantly remote environment, we know that face-to-face interaction is still important. We know that it’s not about a desk, it’s about collaborating with your teammates.

This is exactly why we’ve rolled out features that allow teams to encourage their staff to meet in-person by allowing them to see who is working from where and when. But we didn’t stop there, we also offer services that help employers go above and beyond when it comes to maintaining a great office culture for remote employees – like providing snacks, drinks and workshops.”

This pandemic had a major impact on how Canadians work and use office space. How does Worksimply help companies in today’s current climate of needing flexible hybrid office space?

“The pandemic completely changed the way the world works. Pre-pandemic, the standard was for companies to have one designated desk per employee. Fast forward to today, a lot of companies have gone fully remote while others have embraced a hybrid model.

Now this presents a unique situation. A hybrid model can look very different from company to company, but nonetheless, the office will still play a huge role in how people work.

Moving forward, I think work will take place in three main areas: the home, the central office and finally flexible office spaces close to home,” explained Aoyagi.

This is exactly where Worksimply comes in. Worksimply is helping SMEs not only manage but also support their hybrid workforce by allowing their employees to book office space close to their home or their central office.

Jaime, you saw a new opportunity in the market and decided to double down on it to grow your business. What led you in making this decision?

“The pandemic obviously played a large role in why we decided to double down in a new market. We knew that companies would need on-demand workspace to accommodate their staff with flexible options,” Aoyagi explained.

Thinking 10 steps ahead, Jaime realized that there was a perfect opportunity for him to extend his customer base. “Since we already had space operators and co-working spaces on the Worksimply platform, we quickly recognized we’d be able to serve a new market – SMEs – that would need access to the space operators we were already serving flexible on-demand bookings.

“We sell software-as-a-service to space operators, and today our demand is twofold – on one hand, it’s businesses looking to book space for their employees, and on the other, it’s workspace operators looking for easy-to-use software they can integrate into their operations.”

Groundbreaking ideas are hardly ever lightbulb moments, but rather the result of developing and improving over time. After you made the decision to build in a new direction, what did the process look like?

“Once we realized the toll the pandemic was beginning to take on the world’s workforce and the new wave of opportunity it was creating, we started developing the software for space operators to implement.

As more and more space operators began to use our services, we were simultaneously creating a supply for hybrid-working organizations to choose flexible office space,” explained Aoyagi.

How did the DMZ support you throughout the process?

“Throughout the process, I was able to lean on the DMZ for mentorship and guidance.

As questions came up, I was able to turn to my Program Lead, Mohi Sanisel, who was able to help me navigate through the different challenges that presented themselves.

The DMZ was also able to introduce Worksimply to our first customer leveraging their new model.”

What would you say to other startup founders who are looking to iterate on their core strategy?

“Put your product out there as soon as possible and put your assumptions to test.”

Curious to learn more about what Jaime Aoyagi thinks about the future of work? Check out his recent LinkedIn article here. Looking to provide flexible office space for your time? Head over to Worksimply’s website to learn more.

More than just a buzzword: Taking a “people-centred” approach to business has huge benefits

Having a values-driven mission and people-centred business design can make all the difference for your bottom line – it’s how successful organizations attract great talent and develop iconic products and services.


Just a few short years ago, Sampler’s Founder and CEO, Marie Chevrier Schwartz, was a part of the DMZ where she received mentorship, business support and the connections her sprouting startup needed through what was formerly Ryerson Futures Inc. (now DMZ Ventures). Building on this foundation, Sampler went on to disrupt the traditional product sampling industry and is now recognized as the leading direct-to-consumer sampling platform.

Charlotte Crawford, a former DMZ team member who now works for Sampler, explains what both organizations share in common that make them exceptional places to develop and grow professionally. We sat down with Charlotte, Content Marketing Specialist at Sampler, and Kelly Stewart, VP of Marketing at Sampler, to learn more about Charlotte’s journey at the DMZ, how she launched her career at Sampler and how Sampler prioritizes a values-driven approach to tech and its team.

Could you tell us a little more about your journey to the DMZ?

Charlotte: “I completed my 4-month internship for my Masters in Professional Communication at Ryerson University at the DMZ. 

When I started my Masters, I knew very little about the tech and startup space, but had a growing interest in the field. What really solidified my interest in tech was my media relations professor, Dr. Gregory Levey, who is a DMZ alum, previous CEO of Figure 1 and current CEO of Robinson Huntly, Ltd. It was through his class I was able to conceptualize the pivotal role communications professionals play in the technology and startup space. Once I expressed to him that I was interested in tech, he let me know the DMZ was the place to be.

I remember some of my peers asking me why I was putting in so much effort for an internship during the peak of our school work. I knew the right internship could really go a long way for my future – and I was absolutely correct. My time at the DMZ was not only the highlight of my Masters but also the reason I’m now working for one of Canada’s top growing startups (Canadian Business and Globe and Mail).” 

“I’ll never forget walking into the DMZ and seeing ‘equity over everything’ in neon lights above the door. The culture at the DMZ really made me feel valued, supported and challenged.” 

How was your time working at the DMZ?


Charlotte: “Above all else, the DMZ showed me what I deserve from a workplace. I’ll never forget walking into the DMZ and seeing ‘equity over everything’ in neon lights above the door. The culture at the DMZ really made me feel valued, supported and challenged. 

Throughout my time at the DMZ, I got to sit down with and interview founders and members of the DMZ community. It made me see, firsthand, that it was the people behind the tech that made places like the DMZ and Sampler special. 

I learned that stories of innovation are made relatable and exciting not just through a tech product, but rather the vision, missteps and story behind it. This realization gave me a heightened awareness of the importance in taking a people-centred approach to marketing, content and communications. 

I succinctly describe this approach now as, ‘don’t just tell users how great your product is – show them what it’s like to be on your team.’ This has become my north star for my career.”

How did your time at the DMZ launch you into working full time at Sampler? What attracted you to joining the Sampler team?  

Charlotte: “Before my first meeting with Abdullah Snobar, DMZ’s Executive Director, I was reading up on different DMZ startups. In my research, I found a DMZ podcast episode that featured Sampler’s CEO, Marie Chevrier Schwartz. It was apparent to me how strong Sampler’s value proposition was, but what really got me excited was what Marie had to say about her values in leadership, organizational culture and entrepreneurship. 

I specifically remember Marie discussing how she worked every day for no one else but her employees and investors. She was also asked how she felt about Amazon entering the sampling space and she answered with such confidence because of her belief in her team. 

After listening to the podcast, I told myself that if a job ever popped up at Sampler, I would apply. During my first meeting with Abdullah, he asked me what my favourite startup was. I said Sampler based on how Marie had inspired me during the podcast. I then saw a content marketing position open up at Sampler after I had graduated – it all really felt meant to be.”

An entire team fosters its work culture – what do you think is most important in this process?

Charlotte: “The pandemic has shown us the importance of fostering a values-driven work culture. The companies who have taken direct action to support their employees are the ones who will have great success in the next normal. 

To develop a great team culture, you must commit to living your values every day. It goes further than putting values on your website. It’s fostering a collective understanding of how specific values translate into action on a daily basis.

What really showed the DMZ was living their values was the team’s direct support of community members like myself in achieving their goals. 

I truly had a team of DMZ colleagues cheering me on and directly working with me at every stage of my job search, long after my DMZ internship ended. Nouhaila Chelkhaoui, DMZ’s Women Founders Programs Manager, referred me for my current role at Sampler. Nouhaila, along with Ahmed Saleh, Emily Collins, and Rob Macken all helped me make connections, prepare for interviews, review writing assessments, and find the right knowledge resources.  

“To develop a great team culture, you must commit to living your values every day. It goes further than putting values on your website. It’s fostering a collective understanding of how specific values translate into action on a daily basis.”

Could you tell us a little bit more about your role at Sampler? How did your time at the DMZ prepare you for it?

Charlotte: “This is an exciting time to join Sampler as they have seen so much growth this year as the pandemic expedited the shift to digital strategies for consumer packaged goods (CPG) brands. In my role, I develop organizational storytelling and thought leadership content that positions Sampler as a leader in the product sampling space.

Before I started my Masters, I remember hearing someone in the field say that good communications professionals are the linchpin to organizational success. I understood this idea in theory, but I saw it come to life by watching Natasha Campagna and Ahmed Saleh at the DMZ. They drove organizational alignment, remained so in tune with the broader ecosystem, and were amazing team motivators. Their work highlighted what made the DMZ special.

My time at the DMZ, along with completing my Master’s thesis on Big Tech’s facial recognition technology communications, solidified in me a commitment to take a more innovative approach to communications – an approach that moves beyond standard practice to speak directly to the lived everyday realities of target audiences. These experiences will guide my work at Sampler and beyond.” 

One of Sampler’s proudest achievements is having built a people-centred and values-driven workplace. We know in tech this is not always the industry standard. How do some of Sampler’s values like “ownership, balance, growth and inclusion” translate into daily activities for you and your team?

Kelly: “Weaving our values into everything that we do is truly at the core of our business. To us, you can’t have one without the other. Sampler has a Values Committee that works incredibly hard to ensure we’re living these values both internally and externally, from speaking out on causes that are important to us, to identifying ways that the company can foster work/life balance. They hold the entire business accountable to stay true to who we are, and it’s been such an invaluable piece of who Sampler is.

When it comes to ownership, Sampler has always fostered an entrepreneurial culture around each and every team member’s role. Our staff are experts in their specialties, and we give them the support to grow. Investing in people benefits everyone.

Inclusion is an extremely important value to us and something we continuously work hard to achieve. Recently, Sampler has made the decision to take a step forward in better representing non-binary consumers in the CPG space. Sampler has worked non-binary options into our platform and is actively working with brands to include non-binary consumers into the targeting on all of their sampling programs. 

When it comes to balance, our People Operations team sends out monthly company-wide surveys to get a pulse check on how the team is feeling. It’s created a safe space for everyone in the company to share how they’re feeling. From those results, we’ve launched flex hours, introduced permanent 4.5 day work weeks, and encouraged mid-day breaks. When we get any feedback around stress or burnout we take it extremely seriously and act quickly, which has helped our team trust that their voices are always heard and supported.”

“When you’re able to find talented people who really believe in your mission, the impact on the business is magical.”

Has prioritizing a values-driven workplace translated to your business performance? If so, how? What should early-stage startups think about when building their teams?

Kelly: “Absolutely—without a doubt. When you’re able to find talented people who really believe in your mission, the impact on the business is magical. People can feel how deeply we care for them and their careers, and it shows in the work that they do.

For early-stage startups building their teams, it’s so important to create a safe space to let team members know their voice matters. It’s easy to be too close to the business to really see where you might not be showing up for your team. Step back and see what the day-to-day experience is like for every single person at your company. It can really help to keep your perspective grounded and avoid seeing your culture through rose-coloured glasses. Never ever be afraid of feedback, no matter what stage or level you’re at in your career.”

What is Sampler up to today? 

Sampler has announced their newest tool within their product sampling dashboard, consumer sentiment analysis, which allows brand partners to quickly identify key trends in consumer feedback, effectively segment their audience and plan personalized remarketing campaigns. Check it out here

Want to learn more about the DMZ support that helped pave the way to Sampler’s Success? Click here for more information on our Incubator program.