We recently had the honor of interviewing Margo Crawford, the visionary Founder & Chair of Business Sherpa Group. With over two decades of leadership spanning varied terrains—from high-tech startups to NGOs—Margo illuminated the key experiences that drove her to launch Business Sherpa Group. Her past, colored with co-founding one of Ottawa’s standout startups and orchestrating major M&A transactions, significantly shapes the company’s unique ethos. Margo emphasized Business Sherpa Group’s commitment to supporting SMEs with an approach that’s both adaptable and pragmatic, ensuring longevity for their clientele. Furthermore, she highlighted the team’s varied expertise, which is harmoniously integrated to offer best practices and state-of-the-art technologies tailored for SMEs across provinces. As we mark Small Business Month, Margo generously offered her advice for emerging entrepreneurs, particularly those with a mission to uplift and bolster the growth of fellow businesses.
Margo Crawford is a Canadian thought leader on small and mid-sized enterprises (SME), including SME leadership, succession and strategy. She values knowledge sharing and often speaks both as a keynote speaker and panellist for national events.
In her previous role as President and CEO of the Business Sherpa Group (BSG), she grew BSG to support over 500 small and midsized businesses throughout Canada and internationally by building a team of strategic and operational professionals who provide flexible consulting services in Human Resources, Cloud Based Accounting, Managed Recruitment, and Executive Solutions.
Prior to BSG, Margo was co-founder of Meriton Networks, an optical telecom start-up, and was instrumental in building a company with locations around the world, raising over $75M in equity financing and expansion strategies through M&A. Currently, she sits on the Boards of Digital Opportunity Trust, the Ottawa Network for Education and the Canadian Museum of Nature Foundation. She is a member of the ICD Executive Committee – Ottawa Chapter, the Venture Development Committee of Invest Ottawa and the Ottawa Board of Trade SME Council. She mentors several business peer groups and individual CEOs’ who are scaling and transitioning their businesses.
Margo was named Business Woman of the Year, Women’s Business Network and HR Professional of the Year by the HR Vision Awards.
With over 20 years of dynamic leadership across diverse environments, from high-tech startups to NGOs, can you share with us the pivotal moments that led you to establish Business Sherpa Group?
There were a series of events that catalyzed Business Sherpa Group. One of the first moments that pushed me forward was feeling held back from where I knew I wanted to go. Lacking agency – alongside a belief in myself and my abilities – made me become much more open to taking a risk with my career. This led into entrepreneurship with a tech startup, which unveiled more catalysts that eventually led to Business Sherpa Group (BSG).
The tech startup was a small company that always competed against larger organizations. My role was essentially “everything inside” the business, so I had to wear many hats for many years. This experience was another critical moment on my path towards BSG. I realized that for a business to operate well, internal functions needed proper ownership. Even as the startup grew and we were able to hire resources to take some hats off my head, we never grew large enough to fill all the roles I was doing with full time resources, which is a classic situation small and medium-sized enterprises (SMEs) find themselves in. Being in this situation first-hand revealed a need in the market, and I realized I wanted to try to meet that need. I’d developed a true passion and belief in SMEs; these organizations perform important functions and are leaders in industry, creating great services and products. You could say the tech startup ignited a passion that underdogs can do things really, really well.
One other moment of note is coming to realize I didn’t fit – nor wanted to fit – into big businesses. I deeply wanted a sense of meaningful contribution, which is very much aligned with working in the small business world; you can be a lever rather than a cog.
As someone who co-founded one of Ottawa’s most successful start-up companies and led significant M&A transactions, how have these experiences influenced the approach and ethos of Business Sherpa Group?
A big piece of this was the mentality that you just have to get things done – you didn’t have a choice to not deal with problems, you were the one responsible. This was ignited at the startup where the CEOs often turned to me to solve problems because of my sense of initiative, knowing I would find a way to get it done. This is the first step in leadership, regardless of title. So, initiative and accountability were things I knew straight out of the gate I wanted to cultivate at BSG.
Business Sherpa Group is uniquely positioned with its embedded and flexible approach to support SMEs. How do you ensure this approach remains both practical and sustainable for your clients?
Flexibility, high trust, and strong relationships are key. We know the realities of what it means to be a small business; you have limited resources (money, time and people). Our approach is built around this; we work within each business’ reality, flex to it, and find a solution. We focus on what is the most practical next step forward for a client, mixed with what is relevant and efficient. We ‘quarterback’ in this way and use our team’s collective expertise to provide foresight and do the actual hands-on work too. This is different than a big consulting company that comes in with a pre-built program. We keep our support contained to the realities of the organization and help get clients to a point where a function is fully managed, based on what ‘fully managed’ means to that unique organization.
Working with this approach builds trust, and as you build trust and strengthen the bond, we’re able to be part of a client’s team long-term. Because we have a team and technology working with each client, it’s sustainable in terms of continuity too, creating strength and stability for our clients.
Your team, which spans across Canada, consists of operational professionals, technology wizards, and senior leaders. How do you ensure that their diverse expertise aligns seamlessly to provide the best practices and leading technologies for SMEs in each province?
In terms of being Canada-wide, we like to be ahead of the curve in considering provincial jurisdiction. Thanks to our BSG community, we pool knowledge from each province and have been able to build researched, mapped out playbooks around what are the differences province to province that our whole team has access to. Knowing that you have to be really on top of what is required is part of it and taking proactive steps to cultivate this helps us work in each province, even in the US where justification is much more fractional. This would be difficult for a single individual to do, contractor or employee.
Because of our diverse team, each member has a whole community built in that they can tap into whenever needed. HR is a good example, where the issues that arise are wide ranging and complex. Being able to pull together and tap into the full team’s expertise enables deeper guidance and support. But one of the things we recognize as important is to build out best practices alongside leveraging the knowledge of individuals.
Our expertise is very specifically around the realities of small businesses, and that is unique. This has enabled us to assemble a repository of best practices for SMEs. These are the foundational things that then can be built off of and supported by technology. One example is in finance where we use codified processes alongside technology which maps out what needs to happen when, keeping things on track.
In celebration of Small Business Month, what piece of advice would you offer to budding entrepreneurs, especially those aiming to support and empower other businesses in their growth journey?
To really be connected to your authentic self and know what your personal values are. It’s easy to get pulled and tugged into what you think you should do, how you think people expect you to act, etc. The closer you are to your own personal values, the more it helps you build a stable foundation for your business. Your values are connected to your passion that fuels the problem you are trying to solve. These are handy anchors for when things get tough (because at one point or another, they will).
Communicating your values and passion is also important. It will help attract people to you, ignite your motivation and help build the relationships with your customers because it’s not about you as an individual, it’s about your passion which is connected to a problem that you’re trying to solve for them.
I’d also say to stay connected and really listen to your customers’ comments – the good and the bad. How your customers receive your services is gold, so don’t try to rationalize feedback away. Remain in a client-facing role longer than you want to so feedback isn’t missed because it’s part of the learning process. You can have an idea and the passion, but the most validating feedback on that is how your customer receive it or don’t receive it.
And I’d add the recommendation to not get too attached to the idea that “I’m an entrepreneur”. That’s not what this is about. Being an entrepreneur is an outcome of a bunch of things, rather than an identity. Get attached to your purpose, what you’re serving and how you’re helping people in your own specific way.
As your business grows and staff are inevitably hired, how do you start trusting people with your business?
As you build your business, you build it on your values and your passion. Having people who feel passionately about your business is important yet who also have their own clear set of personal values about how they want to work. Bring in those whose personal values can complement what your business is trying to accomplish. This is critical as business will only be successful if you as a leader can hand off some of your tasks with full confidence and trust. During the early days of handing things off, understand what you as a leader need to feel this confidence and trust so that you don’t unintentionally block progress. For example, if you need more information about how things are going in the beginning, make it clear. But also be careful about when you are going to intercept – when you do decide to step in, do it with a lot of thought so that others can learn and get there footing. This might mean sometimes you choose not to step in knowing there might be a negative outcome. As long as it isn’t business-critical, it’s okay to let you team learn for themselves.
