A smart idea from the early 2000s takes flight in 2010. Today, When I Work serves over 200,000 workplaces in 80 countries, and is focusing its plans for continued growth.

Chad Halvorson’s very first job was bagging groceries and stocking shelves in a grocery store. As an hourly employee, he dealt firsthand with the difficulties of finding out his schedule for the upcoming weeks, which was usually posted a day or two before it went into effect. That first job set Chad on a path to figure out a better solution to a time-consuming and frustrating problem for small and midsize business (SMB) owners and their hourly employees.

A good idea becomes reality.

From the earliest idea in the early 2000s to the current iteration of the company founded in 2010, Chad stayed focused on the core problem of scheduling and communicating with hourly employees. Today, When I Work is a robust SaaS solution that helps businesses with hourly and shift-based employees schedule, communicate, and track time with their hourly teams.

With primary markets of restaurants, retail, hospitality, and healthcare, they are laser-focused on underserved SMBs – delivering a set of modern tools that help them know they have the right people in the right place at the right time. When I Work helps SMBs operate more effectively, run more efficiently, and deliver a vastly better experience for their hourly employees.

When I Work’s model is simple: businesses sign up for a free trial that allows them to get set up on the platform, onboard employees, and build out their work schedules. After that trial period, they can elect a month-to-month or an annual discounted subscription based on how many employees are on the platform. Their popular month-to-month subscription allows SMBs to easily scale up or down and add additional workplace locations as they grow.

“There are over 80 million hourly workers in the U.S., and globally, there are over a billion. Today, we’re looking at what we need to do to have 10 to 20 to 30% of SMBs running their businesses on When I Work,” explained Chad. “We want to make shift work awesome for hourly workplaces and give SMBs access to tools that will help them drive as much success as larger companies.”

Getting support to navigate in the startup trenches.

After a false start in 2004, Chad returned to the When I Work concept in 2008 as connectivity and smartphone gains made the idea more viable. Officially launching in 2010, and after participating in the MN Cup program in 2011, he discovered Minnesota Emerging Software Advisory (MESA) and became fully engaged in MESA’s mentoring program in 2012.

“I was operating and learning in a vacuum, and I needed to learn how to navigate the key issues you encounter when you’re building a software and technology business,” Chad explained. “You can learn a lot from incubators and short-term programs, but it’s unique to get the level of ongoing mentorship and consistent learning that is available to software startups through MESA.”

Through that 10-year mentorship, one of MESA’s longest engagements, Chad was able to work with C-level leaders who had gone through similar challenges and could advise him on issues that included spinning off from another business, financial modeling, raising capital, and scaling the business. During that mentoring period, Chad worked closely with mentors Jeff Fritz and John Tedesco (John recused when he became a member of the When I Work’s board), and then Jim Moar and Jeff Fritz.

“As I look at it, there were three phases of the mentoring engagement. In the early stage we were in survival mode – finding oxygen every day to stay alive. And during that time, I was working through those problems 100% on my own,” Chad said. “The second phase is scaling – building a management team and managing their performance, raising capital, navigating financial transactions, and managing boards.”

“And when you have other leaders in place and they’re highly productive, that third phase is CEO coaching. That’s when your mentors are entirely focused on you as an individual navigating whatever is in front of you. It’s about your personal development, interests, and problem-solving.”

Steady progress and growth.

When I Work’s growth goals are ambitious but realistic given their steady progress and growth. From 2010 to 2021, When I Work realized significant investment milestones. In 2014 and 2015 they landed $9 million in Series A funding, following that with a $15 million Series B investment in 2016. More recently, When I Work received a $200 million growth investment from Bain Capital in 2021 that sharpened its focus and goals for the future.

While venture raises are exciting milestones because they validate that a startup has strong potential and something unique, When I Work had several other developments that contributed to its growth. After the launch of their cornerstone scheduling product in 2010, they rolled out a time and attendance product in 2014. And 50% of their new customers use that time and attendance module along with their flagship product. In 2016, they launched a team messaging product that’s been extremely effective at keeping all communications in one place for their teams – think Slack for SMBs and shift-based businesses with hourly employees.

The success of When I Work certainly shows in its consistent market gains. In 2010, their first year in business, they had 100 customers. By 2012, that grew to 1000 customers and in 2013, they had 3000 businesses on the platform. Fast forward to today, and When I Work has over 40,000 customers across 200,000 workplaces in 80 countries on the platform, and over 2 million employees accessing and engaging with When I Work products.

Giving back to other startups

As Chad charts the next chapters of growth for When I Work, he chose to engage with MESA in a new way. Last year, Chad became a MESA mentor, making him the first mentee to become a MESA mentor.

“I thought I might be able to offer others the benefit of my experiences and scar tissue growing a nascent business,” Chad said. “It’s rewarding to share my perspective with another aspiring entrepreneur, and to continue my learning by seeing new and interesting problems being solved.”

He continued, “MESA mentoring is unique in that it’s a no-strings-attached, long-term relationship. It helps founders and CEOs let down their guard and speak freely and openly about the challenges they face. That leads to very productive dialogues that you can’t always have with other stakeholders that have a vested interest in the business in one way or another.”

“And because MESA’s program is an ongoing and structured commitment, it can have a profound impact on the thinking and decision-making that startup CEOs need to make as they seek to make their vision a reality.”