Heading North: How 360Learning’s Expansion Into Canada Built a New North American Dream Team

Challenges and rewards of targeting talent in a new geography

Expanding a workforce into a new geography is a journey marked by both hurdles and excitement. For us at 360Learning, Canada represented not just a new market, but an ecosystem full of strong talent, innovative spirit, and cultural diversity. As with any journey worth taking, the rewards came hand-in-hand with challenges that demanded creativity, agility, and a data-driven approach.

Identifying key players and competitors

Before diving in, we had to understand the competitive landscape. 

We studied G2 lists, read Glassdoor reviews, and leveraged the networks of existing employees to understand the nuances of the competitions’ offerings. This was crucial not just for business strategy, but for positioning ourselves as an attractive employer. After finding out the “who’s who” of HR tech in Canada, we honed our employer value proposition to stand out in the market, and created a few internal, color-coded reference documents (who doesn’t love a spreadsheet!) as our starting point.

Establishing 360Learning as a recognizable and reputable name

Reputation matters, both as a prospective employee or as a prospective client. We seek to be known as a trusted employer for career growth and development, and also as the creators of the best collaborative learning solution on the market! 

Chief Revenue Officer Chris Bondarenko (Toronto) knows a thing or two about establishing a presence that deserves respect. He’s been a wonderful hiring partner to our Talent Acquisition team. Chris mentions, “Having previously worked for many global software companies, and being located in both Canada and the United States myself, I’ve been impressed with 360Learning’s ability to attract, support, and empower its employees in both countries.”

As we rounded out our first official year in Canada, it is clear that we’ve made some great strides upon which to build. Our name has become more recognizable, one conversation and LinkedIn connection at a time. In most of my interviews, I ask applicants, “had you ever heard of 360Learning before I reached out/you applied?” Around the summertime this year, I started hearing more “yes” than “no,” which bodes well for an informal check on our marketability.  

I also would be remiss to not give credit to our marketing team for creating a recognizable brand. While much of their efforts are focused on generating sales pipeline, the residual effects of these efforts extend to recruitment benefits. They’ve created regular virtual meet ups through our L&D Collective in Canada on top of the great pipeline generation (plus our Head of Demand Generation sits in Montreal). My prediction? Even more collaboration between recruitment and marketing in 2025. 

The HR details: tailoring our compensation & benefits structure

Crossing into Canadian territory meant recalibrating our approach to compensation and benefits. 

Canada’s regulatory framework, healthcare provisions, and employment standards vary from the standards we follow in the US. Navigating these intricacies required developing a tailored compensation & benefit structure that aligned with both local norms and 360Learning’s values. Every offer letter template from our US team was redesigned (a few were translated to French - looking at you, Quebec), and our HR Operations team worked tirelessly to ensure all of our core documentation was applicable to our new joiners up north.

For salary ranges, we divided Canada into a 3-tier system based on market data in Comptryx from Mercer. The most expensive geography–Vancouver, BC–came with higher ranges to match their cost of living. Other cities like Toronto, Montreal, and Alberta stay competitive at our second tier, and our third tier includes locations further away from major cities in Canada. Our general philosophy on compensation is to pay around the 60th percentile for market rates in each geography. 

On top of salary and variable incentive pay, we rolled out a benefit package including: 

• Comprehensive healthcare
• Company equity
• RRSP matching
• Unlimited PTO + holidays + 5 sick days
• A fully remote environment 
• $200 CAD per month for remote working expenses

Regarding recently onboarding in Canada, our newest Enterprise Sales Leader, Celia Cooper, (Toronto) says:

"As a Black woman and the North American Enterprise Sales Director for 360Learning, I am continually inspired by the company’s genuine commitment to embracing diverse perspectives and fostering a collaborative, inclusive culture. From my very first interaction, it was clear that the Canadian expansion was about more than tapping into a new market—it was about valuing the incredible talent and innovation that define this country while recognizing the importance of cultural richness.

Leading a cross-border team in this dynamic environment allows me to see firsthand how 360Learning’s focus on diversity and equity translates into tangible success. The tailored approach to compensation, benefits, and onboarding reflects a deep respect for local nuances and ensures our team is well-supported.

For me, building a team that thrives on inclusion and ambition isn’t just a professional goal—it’s personal. It means creating opportunities for talented individuals to excel while contributing to a shared vision of collaborative, AI-powered learning solutions that democratize learning. Together, we’re not just expanding our market presence; we’re redefining what it means to succeed as a unified North American Enterprise team that performs at a world class level.”

Headcount growth: from 1 to 19 & beyond

When we first set foot in Canada, our “team” comprised a single, pioneering Canadian employee, breaking ground on an ambitious vision. 

Regarding the expansion of our team and the changes around him, Justin Norris offers his candid perspective:

“I was the first Canadian here at 360Learning—alone up in the frozen north, while my international colleagues tried in vain to make sense of my Canadian accent and compulsive apologizing. Well (mostly) just kidding—but let’s not underestimate that it can be a bit challenging to be the only employee in a country.

Fast forward to today, and we have a team of nearly 20 in Canada, including a new Canadian member of my team. It’s amazing having a bigger community of Canadians here (and not just because we’re all so nice)—it creates the potential for more local collaboration, there’s an official 360Learning presence in the country, more HR support for localized programs like matching RRSP contributions, and tons of other benefits. So glad to see us move towards an integrated North American team!” 

As Justin pointed out, our Canadian presence stands at 19 talented team members and counting. Right now, they represent several teams including:

• 11 Learners in Sales
• 3 Learners in Marketing 
• 3 Learners in Professional Services 
• 2 Learners in Customer Success 

This growth is both a reflection of our ability to attract exceptional talent and our commitment to building a scalable, inclusive culture that thrives on collaboration across borders. The outlook for the future?

Adding new and diverse perspectives

Our current efforts

Diversity, equity, and inclusion (DEI) efforts are an evergrowing priority for 360Learning. While this topic can be challenging to tangibly approach, we have always prioritized attaching our efforts to concrete goals. 

We try to match census data around racial and ethnic representation in each country. While we have not achieved minority representation that matches census percentages yet, we’ve made effort toward this goal in the following ways:

• Posting on job boards marketed to protected classes, such as Black or African Americans and Asian Americans
• Testing our job description language through AI tools that detect unintentional gendered language
• Sourcing talent on LinkedIn Recruiter and looking first at candidates who’ve graduated from HBCUs or who are members of sororities or fraternities for Black or African American professionals (Sigma Pi Phi, Alpha Kappa Alpha, etc.)
• Partnering with Women in Sales Everywhere (WISE)
• Finding LinkedIn groups for diverse demographics (such as Black Tech Networks) to join and share job posts
• Gathering anonymous (voluntary) survey data from applicants to identify demographic patterns and trends, and identify where we fall short

Another barrier to our diversity goals is that much of the responsibility falls specifically on North America. Our team in EMEA is unable to track certain types of diversity data due to GDPR, so it’s difficult to get a full company picture. Adding Canada gives us at least two operating countries where we can have a deeper look at our demographic representation. 

Support from leadership

When tackling the topics and goals around DE&I, it is crucial to have buy-in from company leadership. Our Chief Revenue Officer Chris Bondarenko consistently acts as a mentor for #GirlsClub, an organization whose mission is to empower more women in sales to achieve leadership roles. 

On top of his participation outside of 360Learning, he also sees the benefits of having a united team with diverse perspectives in-house: “There is phenomenal talent on both sides of the border and with strong experience in the learning space. We have intentionally established our presence to capitalize on supporting these employees and providing the most positive experience possible. Our approach to hiring the best and most diverse available talent in North America, coupled with our unique Convexity culture, has resulted in sustainable success and growth in the region.”

As the dynamics of DEI continue to evolve across both the US and Canada, our team has focused on creating a scalable effort around DE&I. We’ve created employee resource groups with leadership support including:

• Mental Health 🙂
• Environmental/Sustainability ♻️
• Women ♀️
• Parents 👶
• LGBTQIA2S+ 🏳️‍🌈
• Ethnic Diversity 🤝

There is also an effort to share yearly diversity summaries at least once per year at a company wide level during our regular all-hands meetings. 360Learning’s goal is to lead with empathy, equity, and purpose, and to welcome all voices to the table. 

Team NAMER: embracing North America as a whole

Our expansion has redefined our identity, evolving what was once “Team US” into “Team North America (NAMER).” No longer are we separated by borders; instead, we are bound by a shared vision to transform learning. This shift symbolizes a stronger, more unified front, where collaboration between US and Canadian colleagues is a natural part of our daily operations.

Moving forward, we’re inspired by what we’ve built and the doors it will continue to open. The road to expansion is never easy, but it’s filled with opportunities for growth and connection that redefine who we are as individuals and as a company.

If you’re interested in joining 360Learning Canada, please keep an eye on our jobs page and follow us on LinkedIn! We anticipate further expansion in sales, customer success, and professional services over the course of 2025 and beyond. If you’ve already applied and are preparing to interview, don’t forget to take a peek at our Candidate Knowledge Base as well.