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The Drawing Board: 9 Business Leaders on The Great Resignation, Vaccines, and Their Greatest Hopes for 2022

The Drawing Board is a series by Bay Street Bull that surveys industry leaders on topics of transformation, innovation, and the road ahead.

From perpetual lockdowns to business closures, it’s been a challenging past few years for a myriad of reasons. Through it all, the pandemic has taught us lessons on resilience, innovation, agility, and empathy. For entrepreneurs, it has served as a master class in problem-solving across all facets of business.

As communities open up, we must ask ourselves—what have we learned from it all? How can we be better? Or will we revert back to “business as usual?” From technology to commerce, we asked nine category business leaders to reflect on lessons learned and share their thoughts on the road ahead. From ‘The Great Resignation’ and vaccination policies to diversity initiatives and the industries to watch, read below to see what they had to say.

Colin Druhan

Colin Druhan

Title: Executive Director, Pride at Work Canada

In a nutshell, what is your primary responsibility at your job?

I lead the staff team at Pride at Work Canada, an organization that empowers Canadian employers to build workplaces that celebrate all employees regardless of gender expression, gender identity, and sexual orientation.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

There are lots of arbitrary ways other people will use to define your success. Some of them are useful but most of them aren’t. I strongly believe that personal success is defined within the context of one’s own values and goals. I’m going into 2022 with a good idea of what my goals are, what kind of feedback I’m willing to absorb, and what I’m going to filter out as noise.

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

Something important gets lost when we try to package workforce trends up in this way, and that’s individual context. There is a story behind every resignation, behind every job move. Yes, we are seeing a lot of people make professional changes these days but there’s no single catalyst. The idea that there is a single easy solution, like four-day work weeks or permanent work-from-home setups, is preposterous. You must develop thoughtful strategies that address the specific reasons people might be leaving your workforce.

In general, I always encourage thinking ahead. That’s why professional development for early-career talent is going to become a requirement for more employers as we move forward. If you have good folks working for you, your goal should be for their next big opportunity to be in-house and not with your competitors. If you want people to grow with your organization, you must support that growth, and with actual resources.

What have you found to be the most effective way to attract and retain great talent?

Stop acting like you’re doing people from equity-deserving communities a favor by considering them for jobs. Just that simple shift in attitude is a great start. Today, all the smartest employers are trying to diversify their candidate pools. So, there is tough competition for talent. Be ready to talk about what your business is doing to maintain an inclusive culture; share how you’re changing to respond to employees’ needs as your workforce diversifies, and forget the boilerplate diversity statements on your job postings—they don’t work on their own. Unless there is a logical and explainable strategy behind that statement, it’s a waste of space.

RELATED: LGBTQ+ Entrepreneurs and Organizations That You Should Follow

2021 was a year of big change. Has your leadership style changed since then?

I have a lot less patience for people who feel they need to be convinced to participate in diversity, equity, and inclusion (DEI) strategies. I have a network of hundreds of companies that are already bought in. I know a ton of leaders who are already rolling up their sleeves and getting to work on this stuff. I find it quite sweet when people think we have the time or energy to compel them. They say, “Convince me” and I say, “Sorry, we’re busy doing work with people who can read the room.”

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

I am in the office every day. My partner works from home a lot. I’m just not as productive at home and honestly, we don’t have the space in the apartment for both of us to work from there. 

What have you found to be an effective strategy to manage your time and productivity while working from home?

When I was living and working in the same place, I needed to have a definitive start time for my day. “OK, now we’re working. We’re not reading and we’re not watching anything.” The same goes for finishing up. When I work from home, I need to do something to mark the end of the workday like go for a walk. After that, work is over and life starts. No checking work email, no answering work texts.

Do you think companies should require their employees to be vaccinated?

Yes. Employers have a responsibility to protect the health and well-being of their staff and clients. When it comes to COVID-19, we know that the most effective tool in promoting better health outcomes is vaccines. So, the employer’s responsibility isn’t limited to requiring vaccines, it’s also promoting accurate information about vaccines to mitigate hesitancy and providing any accommodation that might help people to get vaccinated if they face barriers.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

If you have a strong rationale for doing something and you explain it well, you shouldn’t need to worry about something being controversial. “This is the best way to achieve our stated goals and here’s why” works much better than “Every other company is doing this. I guess we have to do it too.” If you find yourself struggling to justify a “controversial” business decision, you need to interrogate why you made the decision in the first place.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

Books: Power for All by Julie Battilana and Tiziana Casciaro and Indigenomics by Carol Anne Hilton

Podcasts: Sway hosted by Kara Swisher (who has been covering tech for over thirty years) and The Argument, hosted by Jane Coaston, both from The New York Times Opinion.

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

I’m excited to see Canada’s DEI ecosystem grow as it responds to expanding business needs. When I started at Pride at Work Canada, I could count the number of large companies we worked with that had a senior-level person looking after DEI on one hand. Today, most companies have at least one person, if not an entire team, working to achieve inclusion outcomes. And thank goodness we’re past the “business case for inclusion.” For the companies I work with, the business case is on their social channels, it’s in their turnover rates, it’s in skilled labour shortages. When it comes to DEI, if you’re still asking, “what’s in it for me?” you’re already done for.

What was your biggest “win” of 2021?

Pride at Work Canada won Best Employer for Diversity, Equity, and Inclusion (Under 20 staff) at the inaugural Charity Village Awards. (Our good friends at Skills for Change won in the 20+ staff category.) This was meaningful because we do DEI consulting as our main business. So, to be recognized for our internal work was motivating for our team. 

What is your biggest hope for your business in 2022?

I hope that as Pride at Work Canada continues to grow, we’re able to thoughtfully cultivate and build on our positive workplace culture. Every member of our team does excellent work. I want to make sure they have as great an experience as we can provide them.

Melissa Allen

Melissa Allen

Title: Executive Director, League of Innovators & Venture Partner, LOI Venture

In a nutshell, what is your primary responsibility at your job?

I lead the vision and strategy of League of Innovators, and support our team in executing on both.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Your “why” is your north star. When you know what your purpose is, you will never be lost. You will always find your way.

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

The past two years have really shown us what matters in life, and I’m personally thrilled when our alumni go on to pursue their passions. That’s what entrepreneurship is all about!

What have you found to be the most effective way to attract and retain great talent?

Community engagement and a commitment to excellence and inclusivity, while working with the brightest, most driven young people in Canada has allowed us to attract the best talent.

2021 was a year of big change. Has your leadership style changed since then?

2021 was about adjusting to this new reality, with an emphasis on leading with conviction and compassion. This is now the norm for all leaders moving forward.

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

We are a fully remote organization, and our team is spread out across the country. Once you get used to managing all the different time zones, it’s actually a lot of fun! We get to stay on top of what’s happening across Canada, we have the flexibility to manage our time in a way that works for us, and the bandwidth that is freed up by not commuting, etc. have meant more productivity, increased quality of work, and more work-life harmony.

What have you found to be an effective strategy to manage your time and productivity while working from home?

Creating a routine, especially in the morning and evening, is a must, as are regular team check-ins. Stay focused on work during “working hours” and maximize your productivity during your own peak working hours. For me personally, that means doing “deep work” between 10AM and 2PM (around meetings!) and then in the evenings before dinner.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

It comes down to having respect and compassion for each other. Always.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

My favourite podcasts right now are Your First Million by Arlan Hamilton, Mission Critical (of course), My First Million, How I Built This (a classic), and Entreprenista.

For books for Canadian leaders and entrepreneurs, I recommend My Life in Black by B. Denham Jolly, the classics Who Owns Canada and Who Owns Canada Now (I wish the author Diane Francis would write an updated one, so much has changed since the aughts), and Your First 90 Days. I can’t wait to dive into Marie Henein’s memoir Nothing But the Truth and Wes Hall’s memoir No Bootsraps When You’re Barefoot comes out this fall.

RELATED: BlackNorth Initiative Founder Wes Hall on the Pace of Progress

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

There are so many! Web3; other tech sub-verticals, such as health/bio/medtech, deathtech (aka legacytech), femtech, fintech, edtech; remote work and the future of work; and for the consumer packaged goods space, I’m confident that there’s still a lot of room for direct-to-consumer brands coming out of Canada to really take off. Indigenomics by Carol Anne Hilton is a must-read to understand the $100-billion-dollar Indigenous economy.

What was your biggest “win” of 2021?

Raising funds to invest in incredible BIPOC founders in Canada and doubling down on my commitment to youth entrepreneurship.

What is your biggest hope for your business in 2022?

2022 is going to be a breakout year for young entrepreneurs and innovators who reflect the diversity we are privileged to have in Canada.

Mike Wagman

Mike Wagman

Title: CEO, Ace Beverage Group

In a nutshell, what is your primary responsibility at your job?

I lead Ace Beverage Group, a leading, fast-growing, and innovative beverage alcohol company in Canada. I focus on growth, strategic direction, and overall company performance.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Stick together as a team. From our executives to our interns, we were able to support each other and glue together as a tight team in 2021, despite a socially isolating year. I’m excited for this vibe to strengthen as we execute our plans in 2022.

There is a lot of discussion around “The Great Resignation.” Has this affected your company? What are your overall thoughts on the matter?

Our job is to attract the best talent and keep our employees empowered and engaged. We are persevering with this strategy despite macro-level disruptions in the labour force. We keep our blinders on and stick to our mission of inspiring consumers with the most innovative and compelling better-for-you beverage alcohol products.

What have you found to be the most effective way to attract and retain great talent?

It starts with our commitment to innovation and operational excellence, which have allowed Ace Beverage Group to win industry awards and gain recognition as a leading industry employer. Internally, we invest heavily in the success of our employees and ensure Ace Beverage Group is a great place to work. We take an employee-centric approach to key policies such as employee benefits, workplace perks, and professional development programs. We empower our employees by treating them like owners and giving them opportunities to contribute to significant new business ideas. We also love tapping into youth talent through co-op programs and internships, which creates a pipeline of workers who gain mentorship and exposure to the beverage alcohol industry.

2021 was a year of big change. Has your leadership style changed since then?

I’ve had to get a little more hands-on. Typically, my leadership style is high-level. I like to establish our vision and make sure the organization has the best people and structure in place to accomplish that vision. This also allows me to work on the future direction of the business and constantly measure whether we are on the right track. With our team more dispersed in 2021, we had to make a bigger effort to ensure our organization was running smoothly and cross-functional collaboration remained vibrant.

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

We miss our open-concept HQ on Geary Avenue in Toronto. Nothing beats the in-person buzz of that space when the music is blaring, samplings are taking place, customer and partner meetings are filling the break-out rooms, and creative sessions are spilling onto the whiteboards. Sometimes it’s nice to have a break for productivity at home but mostly we thrive off the energy of working together in a fun and collaborative space.

What have you found to be an effective strategy to manage your time and productivity while working from home?

It’s been a little easier to get exercise (as long as my kids are in school). I got a Peloton for my home office and joined a tennis club in the summer. Being able to squeeze in daily physical activity (when possible) has been a boost for focus and productivity.

Do you think companies should require their employees to be vaccinated?

The specifics may depend on the business and its stakeholders, but overall we believe companies need to protect their employees and maintain a safe work environment. This includes preventative controls against known health and safety risks. Accordingly, we have flexible WFH policies, require full vaccination status, and a negative rapid test (provided on-site) to enter our offices.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

We try to balance the perspective of all employees along with the values of our organization, as determined by our leadership team. We always want to listen to our employees and understand how controversial topics impact their daily lives. We also work hard, through employee surveys and other workplace policies, to foster an environment of safety, trust, and accountability. At times, we may need to take a stance, even if it leads to conflict. So long as that stance is aligned with our values and is consistent with maintaining a safe and fair workplace, leadership should not be shy to steer the ship in the chosen direction.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

My favourite business podcasts are All-In and My First Million. Both offer tremendous insights from brilliant business leaders. For light-hearted fare, SmartLess is hilarious.

RELATED: How Will Arnett Turned Podcasting Into a Serious Business

Which sectors do you believe will see the biggest growth in 2022? What are you most excited to see grow?

In the beverage alcohol industry, hard seltzers will continue to be the fastest-growing product category as consumers continue to shift their drinking to better-for-you products such as vodka sodas. If the original vodka soda craze was “Seltzer 1.0,” the biggest category growth driver this year will be “Seltzer 2.0.” These full-flavour product types, such as vodka lemonades and iced teas, will drive a new wave of growth for the space.

What was your biggest “win” of 2021?

We launched numerous successful product innovations in 2021 (such as our Cottage Springs vodka water bag-in-box and Cottage Springs vodka lemonade product line) and enhanced our vision and organizational capabilities to support significant future growth. We ended the year with a 25+ share of the Ontario hard seltzer market and number two market position!

What is your biggest hope for your business in 2022?

We have a lot of exciting innovations coming out, especially under our Cottage Springs brand. Our goal is to be the number one better-for-you beverage alcohol company in Canada.

Abdullah Snobar

Abdullah Snobar

Title: Executive Director of the DMZ and CEO of DMZ Ventures

In a nutshell, what is your primary responsibility at your job?

I oversee the overall vision and direction of the DMZ, where we help startup founders build, validate, and scale into world-class companies. My job primarily involves advocating for our role in supporting the startup ecosystem, and the crucial role startups play in Canada’s economy. 

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Incentivizing talent goes beyond the typical perks we used to offer. After losing a physical space, which was traditionally one of the greatest perks you could promote, we need to look at unique ways to keep staff engaged. Building a great team in a virtual setting can be difficult. Leaders need to be creative to generate a strong culture and keep morale high. 

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

‘The Great Resignation’ has affected every business in every industry, and it will continue to impact companies in 2022. I believe this trend is part of the natural evolution of business and life, and frankly, there’s not much we can do about it. Life happens, and for a lot of organizations, this is not a reflection of poor company culture or weak compensation packages. The pandemic has opened up people’s eyes to a new way of life and allowed them to pause and reflect on what they want out of their career, whether it be more work-life balance, being able to travel, or wanting to pursue their own dreams. 

RELATED: How the Employee Exodus Can Spark Opportunity

What have you found to be the most effective way to attract and retain great talent?

Selling your organization’s vision and what you stand for. Prospective talent needs to know your story and company culture, and—more importantly—be motivated to be a part of it. Fostering a strong company culture and community pays immense dividends for your staff and gets them excited about growing alongside the organization.

2021 was a year of big change. Has your leadership style changed since then?

I believe 2021 taught all leaders that leading with empathy is of the utmost importance. It was a stressful year for everyone to say the least, and easing staff burnout and exhaustion needs to be prioritized above all. Companies need to be able to genuinely support their employees and look for ways to support them that go beyond low-hanging fruit tactics. 

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

I think it’s important to note that the DMZ’s ethos is built on community and not a product—we put our startup founders above all and have cultivated a community that is internationally recognized. There’s nothing like being in the presence of the DMZ community, and while working from home has numerous benefits we plan to leverage a hybrid model moving forward. 

What have you found to be an effective strategy to manage your time and productivity while working from home?

Keeping track of my to-do list and prioritizing what’s important. As leaders, we can tend to want to build Rome in a day, but giving ourselves permission to pass things off until the next day is useful and effective. I also try to take constant walks throughout my workday to make sure I’m not glued to my computer screen. 

Which books or podcasts should every entrepreneur add to their 2022 reading list?

Shoe Dog: A Memoir by the Creator of Nike [by Phil Knight] highlights the evolution of Nike and its early challenges to becoming one of the most globally recognized companies. Good to Great: Why Some Companies Make the Leap… and Others Don’t [by Jim Collins’ is a favourite of mine that describes how companies transition from being good companies to great companies, and how most companies fail to make the transition. I’m currently reading Powerful: Building a Culture of Freedom and Responsibility by former Chief Talent Officer of Netflix, Patty McCord, where she shares how to create strong company cultures and high-performing teams. 

I recently launched a new Instagram live series called ‘Made, Not Born’ where I hear from inspiring founders and have raw conversations about the startup journey.

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

I think we will continue to see a rise in e-commerce in 2022. It’s never been more important for SMEs to embrace a digital-first format, as this consumer trend is here to stay long after we overcome this pandemic. Further, as a result of our digital-first world, I expect the cybersecurity industry will continue booming. With more and more of our lives and businesses existing online, protecting our data will be a pressing priority.  I’m personally excited to see the AR and VR space really take off. The metaverse opens us up to a world of new opportunities and will inspire an entirely new bustling economy.

What was your biggest “win” of 2021?

DMZ companies surpassed $1 billion dollars in total funding raised last year, which was a huge milestone for the DMZ. Breaking $1 billion in funding was a testament to the hard world and dedication of all the founders we supported over the years. While early-stage funding for startups remains an uphill battle, it underscored the level of confidence investors had in our tech founders to build world-class businesses.  Moreover, the DMZ’s global expansion in 2021 was a huge accomplishment for us. While the DMZ is headquartered in Toronto, we know that scaling our startups’ success needs to be a global play. Today, the DMZ is situated in more than 10 countries, collectively supporting over 1,000 startups to help them grow.

What is your biggest hope for your business in 2022?

In 2022 I hope to see more growth for the DMZ so we can continue to fill pivotal gaps in the startup ecosystem. Not only are we planning to support more early-stage startups as they grow their businesses, but we’re striving to help founders create world-class companies. 

Erin Bury

Erin Bury

Title: Co-founder and CEO, Willful

In a nutshell, what is your primary responsibility at your job?

As CEO at Willful, my mission is to educate Canadians about the importance of estate planning and to ensure our platform is the easiest way to get a will online. At Willful my core responsibilities are building and retaining a great team of people, managing our funding and growth strategy, setting out our company vision, and ensuring our team is on board with it.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

The biggest lesson I learned in 2021 was about how to grow a family while growing a business. We welcomed our first daughter (a baby girl named Emilia) on November third and since my husband is my co-founder at Willful, we had to put a lot of planning into how we would manage being away from our company. Thankfully we hired an amazing COO who has acted as interim CEO while I’ve been away, and my maternity leave has been an incredible chance to spend time with our daughter while also setting an example for other founders or tech workers who plan to grow their family.

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

As a small startup we know we can’t compete with the salaries of big tech companies, so we have to focus on a total compensation package that goes beyond core salary and benefits. I think this has helped us through COVID-19, since people have come to value things like flexible work, mental health benefits, and other non-traditional benefits. We’ve always placed a big focus on ensuring Willful is a great place to work, from perks like half-day Fridays in the summer to professional development opportunities like courses and annual education budgets, so I think we were well-positioned to continue to build that out and ensure the company continues to be able to attract and retain talent.

What have you found to be the most effective way to attract and retain great talent?

There are the table stakes things—competitive market salaries and benefits, plus all employees are invited to take part in our employee stock option plan. At the end of the day, there will always be another company offering more money, more vacation days, more of something we can’t offer. I’ve found that the best way to retain talent in the face of this is to focus on making sure that people feel respected, that they are well communicated to, and that they are motivated around the same challenge. There will always be turnover in teams so ensuring people feel like they are part of something with purpose and vision is key.

2021 was a year of big change. Has your leadership style changed since then?

Knowing I would be going on maternity leave at the end of 2021, it really challenged me to document all of the things I managed in the business, which was not only a great business continuity exercise but also a great way to challenge whether I was focusing on the right things. Having a few months off to reflect has helped me to reprioritize what I manage on a day-to-day basis at Willful, and to be more intentional about focusing on the big-picture challenges, like our funding strategy, long-term vision, and product roadmap. When I return from maternity leave my leadership style will definitely adjust to being less tactical and more strategic. I have amazing leaders in the business like our CMO Luke Sheehan and CTO Matt McFadyen, and I trust them to execute against our plans with their teams without me being in the weeds.

LISTEN: Everything You Need to Know About Getting a Will

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

Prior to COVID-19, I was always in the office. I hated working from home and rarely did, even though we offered work-from-home days at Willful. That has completely changed since March 2020. Now we are a fully remote company, with a third of our employees living outside our home base of Toronto. My husband and I moved to Prince Edward County full-time, and we’ve found that our company is as productive (if not more productive) while remote. Frankly, no one misses the commute! The big challenge for Willful and other remote-first companies will be how to ensure we have opportunities for in-person collaboration and team bonding.

What have you found to be an effective strategy to manage your time and productivity while working from home?

I’m naturally a pretty type-A organized person, so I’ve always employed to-do lists and other productivity tools. I swear by Asana for project and task management at work, and Todoist for my personal to-do list. I time-block my calendar every Sunday so I have time set aside for strategic or heads-down work, and we also have two blocks of flow time at Willful—company-wide, no-meeting, no-Slack time designed to help people get things done. Other than that I think the biggest challenge is turning off. When you work from home there’s no clear separation from work and home, so I try to go for a walk or cook dinner at the end of the day to signal that I need to turn my computer off and give myself a break.

Do you think companies should require their employees to be vaccinated?

At Willful, our policy is that anyone attending an in-person company gathering or working out of our office must be vaccinated. If folks are working 100 percent remotely, it’s their business whether they choose to be vaccinated.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

We’re not a huge corporation, and the reason people want to work with us is because we lead with purpose and empathy, and because we can go beyond work to create genuine connections with every single staff member about their interests and life outside of work. We don’t want to limit people to only talking about Willful, but we also have to be cognizant of encouraging opinions and dialogue in a way that’s inclusive for everyone, and that keeps the well-being of our team members at the forefront.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

My biggest hobby outside of work is reading, but I don’t read business books, I read for pleasure. My list is full of all types of books, from mysteries to literary fiction to non-fiction. One of my favourite books of 2021 was Empire of Pain [by Patrick Radden Keefe] about the Sackler family dynasty and how they caused the opioid epidemic. It’s maddening but absolutely fascinating. In terms of podcasts, I loved the Bad Blood podcast, which documented the Elizabeth Holmes trial. These recommendations may not be traditional business advice books or podcasts but both have incredible lessons for business owners about ethics, honesty, and the lengths to which some people will go to realize their vision.

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

I think any company that enables online processes or remote collaboration will see the biggest growth in 2022. In the early pandemic, everyone thought we’d be back to in-person appointments and office culture in no time, and now it’s clear that this is a shift that’s here to stay. Companies like Wavy, which we’ve used to manage our virtual team-building events, will see a lot of growth this year. And, of course, companies like Willful are bringing traditional offline processes online!

RELATED: How the Tech is Breathing New Life into the Business of Death

What was your biggest “win” of 2021?

Easy—becoming a first-time mom! Especially knowing that the team in the office was doing an incredible job of managing the business in my absence. A close second would be our appearance on Dragons’ Den, which aired in December 2021. We secured a deal from Michele Romanow, and announced a bridge financing round when the episode aired.

What is your biggest hope for your business in 2022?

My biggest hope is that we can continue to move the needle on destigmatizing conversations about death, and that we increase the number of Canadians who have wills. Currently, 57 percent of Canadian adults don’t have a will, and without one, families are burdened with additional costs, time, and the stress of not knowing whether you’re honouring a loved one’s legacy. Do yourself a favour: spend 20 minutes getting a will. I know it’s on your to-do list!

Greg Gunn

Greg Gunn

Title: CEO and co-founder, Commit

In a nutshell, what is your primary responsibility at your job?

I am the CEO and co-founder of Commit—the professional network for startup engineers where I lead the overall vision and mission for the company while inspiring the team to “Do what’s right for the Engineer.”

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Building a distributed organization has less to do with where people perform their work and everything to do with decentralization and power in today’s business. The more companies can enable their team to take control over their work and time, and base performance off of outcome versus time spent “in office,” the more successful both the employee and employer will be. In line with my primary objective mentioned above, we continue to find ways to build a mutually-exclusive relationship with our engineers and share this way of thinking with our partners and community as change can only accelerate by working collectively. 

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

‘The Great Resignation’ can also be thought of as ‘The Great Reevaluation’ and it is great for our company. At Commit, we are creating access to opportunities through remote asynchronous work and building an equitable work environment for engineers. With many people evaluating their careers and reprioritizing their lives, remote-first companies are offering people the environment and culture that supports their priorities and goals. Going into 2022, ‘The Great Resignation’ will continue to be a hot topic and challenge both young and more established companies to adapt their offerings. 

What have you found to be the most effective way to attract and retain great talent?

Build employment around individuals, not situations. Commit was founded as a remote-first company pre-pandemic, and this decision was made because it is what’s right for the engineer. What is included in building employment around individuals is radical transparency around salaries, interview processes, culture, and policies. By doing so you will attract talent that aligns with your company and deter talent that does not. 

2021 was a year of big change. Has your leadership style changed since the beginning of 2021?

My leadership style is always evolving. I am constantly focused on becoming the best-distributed leader; this means evaluating my habits, actions, network, and beliefs to ensure they are aligned with the vision I have for Commit. 

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

We started Commit before COVID-19 with the thesis that the best companies in the world would be remote-first for two core reasons: access to talent and capital efficiency.

When the pandemic hit, it catalyzed this thesis. Our team felt an additional purpose of providing Canadian engineers with a better way to manage and grow their newly remote-first careers. Because we had a remote-first working environment from the get-go, we had already tested, optimized, and set up the right infrastructure (technology, tools, resources) and ways of communicating (working out loud, repetition, asynchronous) to allow our community and clients to not feel the impact as heavily. 

What have you found to be an effective strategy to manage your time and productivity while working from home?

There is a big difference between working from home and working from home during a pandemic. The first situation is incredible and the second sucks. However, in either case and as a distributed workforce leader, creating a clear separation between work and life is critical for productivity and wellness. 

I do this by being picky about my notification settings on my phone and working only from my designated workspace. As an employer, it is your responsibility to set the culture around work-life boundaries and provide your employees with accessibility to a designated workspace. How this is done looks different for every company, but could take the form of a work from home stipend or a membership to a coworking space. 

Do you think companies should require their employees to be vaccinated?

Commit is a remote-first company that partners with other remote-first organizations, so this conversation does not exist for us. 

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

Talent now has ten times more choice on deciding where to work. Given this, it is important that you make your policies around “controversial” topics known so you are attracting talent who aligns with and complements your organization’s views. The great thing about this is that there are plenty of leaders and organizations with different perspectives. 

At Commit, we are proponents of bi-directional conversations and encourage our team to share their opinions. As our team’s opinions evolve, we will evolve. We want Commit to grow with the people who join.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

I think most people need to read and listen less, and reflect and think more. We all need to spend more time with loved ones and ourselves, and actually consume less content. 

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

Asynchronous collaboration tools. Remote-first does not remove the need for team communication and connection, which is why I am particularly excited by the continued growth of core collaboration tools that support connection and enable strong asynchronous collaboration.

What was your biggest “win” of 2021?

Raising Commit’s six-million-dollar USD seed round, after bootstrapping for 1.5 years. This raise was a pivotal moment in Commit’s journey as it validated the need for a frictionless path between software engineers and world-changing opportunities.

What is your biggest hope for your business in 2022?

We have some really exciting product launches coming this year that are focused on scaling the size of Commit’s network and increasing user collaboration. I am looking forward to having more engineers join the most collaborative technical community in the world. 

Shadi McIsaac

Shadi McIsaac

Title: CEO and co-founder, Ownr

In a nutshell, what is your primary responsibility at your job?

My primary responsibility is to help entrepreneurs start and grow successful businesses by removing some of the barriers to entry. Through Ownr, we empower and equip both aspiring and existing entrepreneurs in Canada with easy-to-use, accessible technology and support so they can focus on what’s most important.  

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Last year made clear to me just how resilient Canadians are when it comes to taking charge of their own livelihoods, even in the face of remarkable challenges. 

Entrepreneurs are a prime example of this. They’re change agents—not only changing the trajectory of their own lives but that of their community and the economy. Launching a business in spite of all the challenges the last few years have thrown at the world takes strength. 

That’s what excites me most about what we’re doing at Ownr. We are supporting people’s aspirations from the inception of an idea and beyond, empowering them by creating a space to grow their business the way they want. Entrepreneurs are resilient, and that notion inspired me and the team to keep pushing, to keep finding ways to help lower the barriers to business ownership and make the aspirations of entrepreneurs a reality. 

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

Being a digital-first company that offers flexible work options (and easily pivoting to work from home whenever needed)m it hasn’t affected us very much.

That said, as we grow and scale Ownr, we are not immune to the pressures of the competitive labour market—especially as securing talent becomes borderless. That growing global challenge has only reinforced our desire to develop and grow talent from within Ownr, helping our colleagues become stronger leaders that are able to grow alongside our business. I believe this strategy adds so much value to our business, both directly and indirectly. 

What have you found to be the most effective way to attract and retain great talent?

In my eyes, it all comes back to our mission statement: empowering entrepreneurship through accessible, digital tools and services to help individuals start and grow successful businesses. Core values like that help attract like-minded people who are intent on developing their careers and we are proud to help empower them to meet their goals.

2021 was a year of big change. Has your leadership style changed since then?

My leadership style hasn’t changed, per se. If anything, the turbulence of the pandemic has really solidified it. My focus has been (and will continue to be) trusting my team to own the decisions while I own the outcomes. In other words, creating a space for my team to do their best work and trusting them to make decisions that drive the business forward. 

We always take external factors into consideration when making decisions for the company, and we found ourselves doing this even more so during the pandemic. We’ve had to get comfortable with a state of continuous change and adaptation, and I think we’ve excelled. 

One thing I’ve tried to remember is that we’re all in the same storm, but not all of us are in the same boat. The pandemic has also changed each individual’s lifestyle, including where and how they work and under what circumstances. You have to be empathetic to both your team members and yourself because the past year has had a profound impact on everyone. I hope I’ve been able to express that empathy and understanding for my team. I have so much gratitude for how my team has shown me kindness and understanding throughout this past year, too. 

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

I’ll admit, I get a lot of energy from being in the office with my team. There is nothing like problem-solving and brainstorming with a few laughs along the way. Having said that, I’m proud of my team for seamlessly pivoting to remote work when necessary. On a personal level, the time spent working from home made the transition back to the office more palatable for me after a brief maternity leave. 

Despite last year’s challenges, our team size has doubled (currently 50+) and we hope to double it again before 2022 is out. We’ll be digitally onboarding and welcoming our new team members online and adapting however needed along the way. This type of resilience signals, to me, that Ownr’s culture is resonating even in a digital environment. Our team continues to be inspired and has a strong desire to stay connected, build relationships, and meet goals despite the physical distance. 

Long-term, I think the synchronized hybrid model is how our team will ultimately function, taking advantage of the benefits of both in-person and remote work environments.

What have you found to be an effective strategy to manage your time and productivity while working from home?

I’m a huge fan of a daily ‘digital detox.’ I turn off my phone every evening at 5:30PM until my children’s bedtime. This allows me to be fully present with my family and offers some time and space from work. 

I find this to be effective for two reasons. For one, I believe the line between work life and home life has become increasingly blurred and I’m determined to set an example to my team that balance is crucial. Equally, I believe to be effective as a leader, you need to allow time for reflection, which can be hard to find if you’re lurching from one meeting or email or call to the next. I believe it’s important to afford yourself perspective to think critically about yourself and your business.

Do you think companies should require their employees to be vaccinated?

Each company will have its own policy based on what they believe to be the best course of action. For us at Ownr, that’s provided by RBC Ventures and our parent company, RBC. 

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

As a wholly-owned subsidiary of RBC, Ownr benefits from a large Human Resources capability. I’m fortunate to be part of a broader ecosystem that extends these capabilities to me and the team as we navigate different discussions. 

Which books or podcasts should every entrepreneur add to their 2022 reading list?

I really like the Armchair Expert podcast, by Dax Shepard and Monica Padman. It crosses a variety of topics with diverse guests—journalists, academics, celebrities—and talks about the challenges of life that often lead to growth. I feel like I learn something new every time I listen.  

In terms of books, I just cracked the spine of Ray Dalio’s newest, Principles for Deadline with the Changing World Order

Beyond that (while it’s not necessarily an entrepreneurial-themed pick) I also recently read Marie Henein’s memoir, Nothing but the Truth. It is a powerful totem to the immigrant experience and offers Marie’s expert perspective on the privileges afforded to us in a democracy inherently underpinned by a strong judicial system.

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

In 2021, there were more Google searches for ‘How to start a business’ than ‘How to get a job.’ That data trend and the interest it underpins is an incredible affirmation of the opportunity at hand for Ownr. That makes me excited about Ownr’s potential to become the default destination for entrepreneurship in Canada.

What was your biggest “win” of 2021?

My biggest “win” in 2021 is more of a personal one. My husband and I welcomed our second son, Julian, in May. That win is tough to beat. 

Professionally, I think the integration of our first acquisition, Founded, was an incredible gain in 2021. It allowed us to bring in the best legaltech capabilities to market and be a trusted source for Canadians turning to entrepreneurship during the pandemic—all inside of four short months.

What is your biggest hope for your business in 2022?

I believe I’m paraphrasing Anderson Cooper here when I say, for Ownr, “hope is not a plan.” 

Our team’s plan for 2022 is to deliver and expand our best-in-class incorporation and company management services across Canada. We want to delve beyond company formation and into new verticals to support entrepreneurs along their journey. 

Ghassan Halazon

Ghassan Halazon

Title: Founder and CEO, EMERGE Commerce

In a nutshell, what is your primary responsibility at your job?

As CEO, I am in charge of setting the vision for the company, and ultimately overseeing all major strategic decisions across the organization, from key hires to mergers & acquisitions (M&A), to PR and investor relations, and, of course, to managing the business.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

Patience. Most of us expected a return to normalcy by now and it hasn’t happened. We have learned the hard way to keep our heads down and stick to executing relentlessly. The rest will follow.

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

On average, the impact is more pronounced than in previous years and probably a function of EMERGE becoming a higher profile, public company. That said, I wouldn’t say people have been leaving at an alarming rate. By that same token, we have grown our company substantially over the past couple of years, from approximately 30 team members to over 115 employees. Overall, I believe companies that do not do a good job of keeping in touch, articulating their vision, and, most importantly, listening to their employees will find it hard to compete in today’s job market.

What have you found to be the most effective way to attract and retain great talent?

It starts with simply listening to them. They want to be heard and deserve to be. We also encourage team members to get together and organize periodic events for them to ensure everyone keeps in touch and feels connected.

2021 was a year of big change. Has your leadership style changed since then?

EMERGE’s headcount has grown substantially over the last year, in large part due to the four brand acquisitions we have completed. That’s quite a bit of culture to integrate! My leadership style has skewed towards learning a lot more about each team member’s ‘super power’ (everyone has one) and then assessing how best to transfer that strength to the rest of the organization.

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

Like anything, there are some pros and cons to remote work. Over time, I have developed a routine that works great and see that the team has been executing surprisingly well remotely. I would prefer some more human interaction and get-togethers, which I think are in the cards soon, but I believe the five-day workweek as we know it is a thing of the past at this point.

What have you found to be an effective strategy to manage your time and productivity while working from home?

A super organized to-do list and an up-to-date calendar are really the starting points. I would also say separating my work life and space has been critical to productivity. Beyond that, I would suggest dressing up!

Do you think companies should require their employees to be vaccinated?

I don’t think companies should require it but I do think that employees should be vaccinated for their safety as well as everyone else’s.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

By being transparent and open. Encouraging plenty of questions and actually listening to and addressing any concerns as they arise. The worst thing a leader can do is be distant in times of major change and uncertainty.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint to Success [by William Thorndike.] It’s a book about the unconventional philosophies and techniques that led some world-class CEOs to outperform the broader market by a very large and sustained margin.

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

I think Web3 is super exciting and will only gain more relevance. I’d have to also say e-commerce, regardless of whether the ‘stay-at-home’ climate is expected to wind down or not. The fact of the matter is, e-commerce still has a long way to go and trillions of dollars will be shifting online over the next decade.

What was your biggest “win” of 2021?

Following our go public, we completed three terrific e-commerce acquisitions and, in the process, grew pro forma revenue by six times and EBITDA by nine times. It was a historic year for us by all means.

What is your biggest hope for your business in 2022?

Beyond the health of our staff and broader community of partners, I would say a stable macro-climate to operate in. There are a number of macro headwinds across the globe (inflation, supply-chain, rising interest rates, etc.), I hope these issues don’t turn into bigger fires. Either way, we’re ready as ever to tackle any cards handed to us.

Adam Gellert

Adam Gellert

Title: Founder and CEO, HiredHippo

In a nutshell, what is your primary responsibility at your job?

Leading our company on our mission to create the future of hiring through transparency and an improved candidate experience.

What is the biggest lesson you learned in 2021 that you’re taking with you into 2022?

That time is the most valuable gift you can give and receive; stay interviews will replace exit interviews; flexibility will beat a four-day work week; candidates favour trust, autonomy, and transparency over compensation; and radical candour is the greatest form of flattery

There is a lot of discussion around ‘The Great Resignation.’ Has this affected your company? What are your overall thoughts on the matter?

From our perspective, candidates always come first. It’s been a candidate’s market since there were options for career growth, work environment, location, and compensation. I hear companies say the pendulum will swing back. No, it will not. It will always be [a candidate’s market] as long as there are options.

Companies that focus on building an attraction strategy for the long-term that is transparent and open and improves the candidates’ experience make hiring and applying much easier for everyone.

What have you found to be the most effective way to attract and retain great talent?

Build a culture where the people who leave speak highly of you. When you hire, understand the business problem the role you’re hiring for will solve, and use processes that match and attract the right talent. Above all else, alignment at the beginning of the hiring process is more likely to reduce costs, improve time to fill, and result in a long-term fit. The best part is, it’s free. A focus on understanding motivators for changing careers to match and align upfront has been key to hiring success on our platform between employers and candidates matched on HiredHippo.

2021 was a year of big change. Has your leadership style changed since then?

I never like when people call me their boss and consider everyone on my team as equals. When everyone is equal, leading is just about doing absolutely anything to support your team, listening, and getting out of their way. We’ve always had core values of trust and transparency. When things changed we were prepared, but it’s become more clear to me that these things are fundamental to the success of our team.

Do you prefer leading your organization from a work-from-home or office setup? What has your experience been like?

Our team’s productivity skyrocketed with work-from-home and we found there was an increase in overall satisfaction in the work being done. The autonomy and trust to work from anywhere (whenever possible), means great things to our team. We’ve always been a flexible environment with no set hours and open time-off policies so we were naturally set up for the changes we saw in the world of work. I think the future is hybrid, to give people the option. But, every company and person is unique.

What have you found to be an effective strategy to manage your time and productivity while working from home?

[If you] do work you care about in an environment where you can flourish and with the compensation you need, it won’t feel like work. Also, setting an intention in the day and using time blocking while being ruthless with your time is key.

Do you think companies should require their employees to be vaccinated?

I’d leave that to each individual company to make that choice.

How do you plan on navigating “controversial” topics like vaccinations and politics with your team as we re-emerge from the pandemic? 

I am of the opinion that we can use critical thinking, self-awareness, and compassion to communicate about difficult things in the workplace. I have an open-door, non-partisan approach to discussions with my employees. All questions and concerns are valid, and while I may not have all the answers, I refer to the facts and use data to inform my decisions and always recommend they do the same.

Which books or podcasts should every entrepreneur add to their 2022 reading list?

Podcasts: How I Built This by Guy Raz and Masters of Scale by Reid Hoffman

Books: Radical Candor by Kim Scott and Black Box Thinking by Matthew Syed

Which sectors do you believe will see the biggest growth in 2021? What are you most excited to see grow?

Creative industries because content, brand, and web3 will lead the next decade. Healthcare because we need a better way to protect our future. Customer success because it will be harder to hold a customer’s attention. Hiring, which I think every leader should own and get better at it. Technology and robotics because we’ll see many jobs and industries replaced or made more efficient. Skill Trades because we’ll care more about the structure of things as everything becomes more online and hospitality because people will crave more experiences

What was your biggest “win” of 2021?

Tripling our business and helping our clients see success through improvements in the candidate experience.

What is your biggest hope for your business in 2022?

Our mission is to be the number one way Canada’s growing startups and small-medium businesses attract, engage, and hire customer-facing and technical talent.

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