Most business histories are tidied up after the fact into a story of steady progress toward an obvious goal. The history Scott Kendall publishes about his own company is refreshingly not that. It begins in 1992 with part-time computer repairs for family and friends, passes through two complete changes of business name and one abandoned business model, and arrives at Outhouse IT in 2010. For a Greater Toronto Area business owner wondering whether their own path has been too indirect, it is an instructive account.
The company provides managed IT services to small and medium businesses across Southern Ontario, specializing in organizations with roughly 5 to 100 employees. Its services cover managed services with round-the-clock monitoring, cloud computing, help desk support for network, PC, software and virus issues, network security, and remote IT services. The proposition is stated plainly as a cost-effective, full-service alternative to an in-house IT department, providing businesses with the support, guidance, and security expertise they need without building an internal IT team.
That target range of 5 to 100 employees is a more meaningful piece of positioning than it might appear. A business with four staff can manage technology informally. A business with two hundred can justify hiring IT personnel. The band in between is where the problem is genuinely acute, because the organization depends on its systems but cannot yet support the people who would maintain them. Naming that range explicitly means a prospect recognizes immediately whether the firm is built for them.
The company’s history explains how it arrived at that focus. Kendall began in 1992 offering computer repairs to local Toronto small businesses, following his father, who had run a computer service company in the 1980s. The business traded first as Computer Consulting by Scott Kendall, then as The Technology Coach, before becoming Outhouse IT in 2010. Each name reflected what the business actually did at the time rather than an aspiration.
The decisive change came in late 2009, and it involved giving something up. The business had been oriented toward training, and Kendall describes enjoying being in front of an audience. He concluded nonetheless that IT services and support were his real interest, and that a flat-fee service model was the objective worth pursuing. The shift was from computer repair and training to operating as a client’s full IT department.
The flat fee is the commercial centre of the business, and it addresses a genuine misalignment in the industry. An IT provider billing hourly earns more when systems fail and more again when repairs take longer. The client wants neither. Under a flat monthly fee, the provider’s incentive reverses entirely, because every prevented failure improves their margin. The company frames the client benefit in terms of reducing downtime, preventing technology issues before they disrupt productivity, and budgeting a predictable figure rather than absorbing unexpected repair bills.
The team is published with unusual candour about individual backgrounds. Systems analyst Slavik Koustov, with close to five years at the firm, is credited with implementing streamlined onboarding processes, improved password management and two-factor authentication, alongside testing environments and automation flows. Support specialist Jeremy Pitman brings a background in psychology and more than a decade in technology, including roles at Walt Disney World, Apple, where he worked at the Genius Bar and as a technology educator, and Tesla, where he became the in-house systems expert. He is pursuing further certification through Google IT support courses.
Those profiles point at something the company understands well. Technical capability is assumed in this market. What distinguishes a support provider is whether the person arriving can explain a problem to a non-technical owner clearly, provide practical recommendations, and help the business make informed technology decisions. A psychology background and Genius Bar experience are unusual credentials for IT support, and entirely relevant ones.
Kendall notes that several client relationships are now measured in decades, and that he personally selects each team member to ensure alignment with what he calls a culture of helpful support. For a firm this size, a founder involved in hiring is how service consistency is maintained.
The company publishes frequently on subjects its clients face directly, including cybersecurity, artificial intelligence governance, the hidden costs of reactive technology management, and practical IT planning for growing businesses. The artificial intelligence policy piece is particularly well judged, because staff in most small businesses are already using these tools without guidance, and the resulting data exposure is a risk most owners have not yet considered.
For Canadian small and medium sized businesses, the first lesson is about the long path. Eighteen years passed between the first computer repairs and the arrival of the current business name and model. Two names were discarded. A training business that was working was set aside for something judged better. Owners whose businesses have changed shape several times should recognize that as a normal process of finding the right model rather than evidence of drift.
A second lesson concerns pricing that aligns interests. The flat fee removes the suspicion a client might otherwise carry about whether a provider benefits from their problems. Businesses whose pricing creates that tension should consider what removing it would be worth in trust and retention.
The third lesson concerns defining the customer precisely. By focusing primarily on organizations with 5 to 100 employees, the firm has built its services around the needs of businesses that depend on technology but often lack dedicated internal IT resources. Precision about who you serve is usually more persuasive than claiming to serve everyone.
Your role in staying up to date is integral to our shared mission of fostering a community of innovators. CanadianSME Magazine is a valuable treasure trove of entrepreneurial knowledge. Click here to subscribe to our monthly editions for updates on Canadian businesses. Follow our handle @canadian_sme on X to remain updated on all business trends and developments. Your support is crucial to our mission.
Disclaimer: This article is based on publicly available information intended only for informational purposes. CanadianSME Small Business Magazine does not endorse or guarantee any products or services mentioned. Readers are advised to conduct their research and due diligence before making business decisions.
