Quick growth forced Canadian startup Gryd to scale from two to 30 team members in a short period of time. CEO and co-founder Josh Glow shares strategies to hire the right people, foster unique company culture, and avoid turnover.
Building the right team is one of the biggest challenges early and growth stage startups face. Hire the wrong people, and you risk stunting your company’s growth or spending precious time and money course-correcting. But, get your key hires right, and you’ll set up your startup for long-term success.
When it comes to recruiting, hiring, and onboarding talent, the stakes are high, which is why it’s crucial to strike the correct balance between efficiently bringing on the talent you need and preserving your company’s unique culture.
Josh Glow, CEO and co-founder of Winnipeg-based Gryd, a PropTech startup that creates innovative tools for property managers, owners, and REITs to optimize their businesses, recently sat down with us to discuss how his team quickly scaled from two (including Glow himself!) to 30.
Below, Glow shares how he led this pivotal growth phase, as well as tested strategies for making key hires, with an emphasis on building and nurturing culture to increase autonomy and avoid turnover.
Which key hires should a founder make first?
The most daunting question for many founders is, where to even begin building your team? Should you focus on filling out an impressive C-suite or build from the ground up? What roles make the biggest difference during a startup’s earliest stages?
In his experience with Gryd, Glow says the best approach was to begin by strategically letting go of tasks that could be easily delegated and hiring a primary salesperson.
“At the beginning, I was doing every single position, so I had to figure out what I could let go of,” says Glow. “What can other people do better than me? What would be best for the business? Even now, every couple of years, I struggle with that. I have to strip off a piece of the job that, usually, I love and hand it to someone else.”
First up for Glow: bookkeeping. “I was doing the accounts payable, receivable, and all the accounting in the evenings, and I actually enjoyed doing it. But, getting a contract bookkeeper took a huge load off my plate.”
His other first key hire was a salesperson. He reasoned that, once sales grew, it’d quickly become possible to hire more team members. “If there’s a product ready to go, sell what’s on the truck,” says Glow. “Good salespeople are also a smart early hire because of how their commission structure works, so they’re a net positive to the business and a critical role.”
“When the right people come along who are willing to get their hands dirty and set egos aside, whether they’re C-suite or not, those are the most important hires.”
Rather than focus on filling specific job titles, Glow prioritized attracting and hiring the right people for his long-term vision. “When the right people come along who are willing to get their hands dirty and set ego aside, whether they’re C-suite or not, those are the most important hires,” he says. “That can evolve into a C-suite down the road, but humble people who are talented and willing to go all in are what’s needed most.”
Glow shares an example of how Gryd extended themselves in their early days to bring on the hire who’s now Gryd’s CFO. “He wasn’t in our budget for another couple of years — and he knows this — but because he fit in so well culturally and was willing to lend his hands to so many different areas of the businesses, he still joined us until that CFO role became available.”
Hire slow and optimize for cultural fits
As Gryd continued to grow, first in a growth spurt from about four to 14 employees, and soon thereafter in another up to 30 team members, culture only became more important to the startup’s hiring process. It would’ve been easy to give into the temptation to recruit and onboard new employees as quickly as possible, but Glow doesn’t believe that would serve anyone well in the longer-term.
“Some other founders have always said, ‘hire slow and fire fast.’ Forget the firing part- doing our due diligence and really taking our time in the process has become a key part of our hiring philosophy,” he says. “Turnover is such a cost to businesses that many founders don’t think about very much.”
“It’s very important to articulate the do’s and don’ts, and how a company’s culture functions, before a new employee even starts.”
A big part of Gryd’s due diligence centres around assessing cultural fit. “Culture fit is the biggest thing,” says Glow. “It’s very important to articulate the do’s and don’ts, and how a company’s culture functions, before a new employee even starts.”
To that end, Gryd established a robust set of core values they want candidates to align with, even in the early interview stages. They go so far as to discuss each value with every single potential employee in their second interview. These values — which include being forward thinking, embracing collaboration, having fun, and believing in what Gryd is building — aren’t just words on a wall, either. Glow makes sure they’re actively enforced throughout the employee experience, through team events and by making a point of celebrating team members who embody these values. Once a year, “Off The Gryd,” an annual retreat, takes place, where employees fly into Winnipeg from all over the country to do a focus week of work alongside something fun, like adult summer camp.
Crucially, Gryd’s core values haven’t changed in years. “Establishing those with the core team early on, and then providing autonomy to the team to hire according to those values increases alignment from the start,” says Glow. “In fact, I only wish we’d done it earlier!”
Gryd CEO and co-founder Josh Glow
Plan strategically and balance your startup’s workforce
As Gryd grew, Glow also realized the importance of implementing a more structured approach to shaping the startup’s workforce. When they reached around 15 employees, Gryd brought in an external advisor to facilitate a comprehensive strategy session. The idea wasn’t to have someone come in and tell Gryd’s team how to grow, but rather bring in someone educated enough on the subject to, in Glow’s words, “not necessarily contribute, but guide the conversation from a clean slate and facilitate looking at things from different angles, which was really refreshing.”
He calls the session a game-changing moment for the company: “We now have a very well-articulated and laid-out strategic direction for team growth that we revisit every two years.”
A key outcome of that process was a realization of the need for a balanced workforce—not just a team of advanced accreditations or expensive degrees, but a mix of people skilled in execution and those driven to push the company forward through leadership.
“If you have a company full of managers, and no one’s doing individual contributions, it’s not going to work.”
“You need a balanced workforce to thrive,” he explains. “If you have a company full of managers, and no one’s making individual contributions, it’s not going to work. It’s also not going to work if you only have individual contributors.”
The strategy matrix they developed also provides an “instruction base” for different role types to thrive, giving each clear ownership and goals, as well as autonomy that Glow sees as key for both individual and collective success.
Use remote work to your advantage
One of the key advantages that allowed Gryd to scale so rapidly, and successfully, is their embrace of a remote-first model. “We quickly adjusted our hiring strategy to ‘best person across Canada,’ rather than ‘best location,’” says Glow. “We allow people to choose their own adventures and live in different cities. That really opened up a lot of doors and conversations, which allowed us to bring in the right people.”
Of course, growing and managing a distributed team comes with its own set of challenges. “It can be very easy to become disconnected from the team if you don’t have things constantly pushing it,” says Glow. “You’re not walking by someone’s desk and asking how their day is. Instead, you have to open up a chat and type a message.”
To combat this, Gryd uses a variety of tactics to keep employees engaged and collaborating, which also helps prevent culture rot and high turnover. This includes virtual happy hours, weekly all-hands meetings, fun competitions, and frequent surveys to stay on top of morale.
“To be honest, some of the best success I’ve had with key hires came from just sliding into their LinkedIn DMs.”
The remote advantage means Gryd takes a multi-pronged approach to sourcing top talent, including leveraging partnerships with organizations across the country to share job postings and get them in front of key pools of potential recruits.
Glow also finds LinkedIn has become an increasingly valuable tool. The team doesn’t just post and pray though—they’re proactive in searching the platform and reaching out directly to promising prospects. “To be honest, some of the best success I’ve had with key hires came from just sliding into their LinkedIn DMs,” says Glow.
He says this personalized outreach is optimal for a startup that prioritizes long-term fits, not just short-term fills.
Grow into the future with culture-centric hires
As you work to build your startup’s workforce, consider taking a page from Glow’s playbook and make culture a north star—not just an afterthought. By establishing a clear set of core values from the early days and weaving them throughout your hiring and onboarding process, you increase your chances of successfully scaling your company without sacrificing the unique traits that make it special.
Invest time upfront to define your guiding principles, then empower your team to hire and operate according to them. Continuing to reinforce those values through team rituals and celebrations is key. With the right people in the right roles, you’ll be well on your way to building your dream team.
If you would like to learn more about Gryd, visit their website: Gryd.com
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