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The Breeze Behind the Sails of Your Business

Empowering Managed IT Support & Technology Services to Businesses Across the BC Interior, Provided by Our Honest, Friendly, and Personable Team Based in Kelowna

West Kelowna, BC

High Winds & Smooth Sailing

All Hands on Deck

You Care For Your Customers. We Care For You and Your Team.

We’re a team of IT specialists that put serving people and making a positive difference at the heart of everything that we do. We’re not only here to serve as your business’s can-do IT crew, keeping your ship sailing smoothly and securely in today’s digital waters, we’re strategic IT partners that help your business to navigate the tech tides and make them work in your favor.

Downtown Kelowna at the sails.

Full steam ahead!

We Care, We Listen, We Get It, and We Got You

Tailored to focus on benefiting our clients’ unique needs and helping them to achieve their goals securely, we offer a full suite of IT solutions with a can-do, personal approach. At its core, our approach is about caring, listening, understanding, and acting in your best interest.

We offer fast and friendly IT support, robust cybersecurity solutions, and empowering IT strategy services that keep your tech fast, reliable, secure, and aligned with your wider strategic goals. Professional in our approach but human in our relationships, we’re IT people that your team will love working with. For us, providing great results and warm smiles is a natural part of what we do!

Keep The Wind Behind Your IT's Sails

To get the best from your tech, having deep and responsive support from a team that your people love working with can make all the difference! Our team don’t do technobabble, we’re here to help, solve problems, and keep your ship smoothly sailing. 

Canada and lake in Kelowna - brown wooden dock on body of water during daytime

Sail With Confidence​

We’re experts in cybersecurity who know how to keep businesses in safe harbour. Our cybersecurity tools secure your data, empower business continuity, and minimize cyber risks for your business, enabling you to focus on what you do best, while keeping cyber pirates at bay. 

Downtown Kelowna at the Dolphin statues

Map and Compass

Businesses can get ahead and look forward when their technology is aligned with their needs and goals. We help our clients to identify risks and opportunities in their own and the wider tech landscape, and design solutions that enable your business to achieve more using less, unlock more scalability, and sharpen its competitive edge. 

Kelowna - people on beach during daytime

Navigate Your Compliance Seamlessly

Enforcing compliance and scaling it with your business can be tricky without the help of technology. We help our clients to align their people, processes, and technology together, giving better observability, control, and reporting capabilities that make compliance a breeze.

Photo of beach, grey, nature and sea in Kelowna

Are You Ready to Set Sail?

Need a hand with a tech challenge? Have questions? We're here to listen and help! It all starts with a conversation.

Anchored in Integrity

Your Success = Our Success

Communication, integrity, and honesty are all integral to exceptional IT. We don’t just measure our success by measuring the performance, uptime, and security of your IT environment, we measure it by listening to your business and working closely with you to ensure that we’re doing all that we can to provide efficient and empowering technology for you.

IT Support

Everything that your business needs to enjoy a fast, secure, and reliable IT environment, IT Essentials offers rapid helpdesk support for your team and monitoring and care for your devices, hosting, infrastructure, and network.

Cyber Security

Protect your users, network, and your data from incidents and cyber threats. We offer a full cybersecurity solution including user training, network and device protection, zero-trust solutions, and data backup & recovery.


Set sail to a more cost-effective, scalable, secure, and powerful operation with our cloud solutions. We offer tailored implementations and IT support for Microsoft 365, cloud hosting solutions, and remote desktop capabilities.



We offer cost effective and tailored co-managed IT solutions from a team that your business and customers will love working with! From first to third line helpdesk support, to specialist expertise in networking, cloud, and cyber security, SkySail can act as natural extensions of your IT department.

SkySail, the safe harbour for your business

The Trusted Approachable Technology Partner to Businesses Across the British Columbia Interior

Whether you need help with ensuring compliance adherence, help with an IT project, or support with specialist software, we’ll be glad to meet with you, listen carefully to your needs and goals, and help you to move in the right direction for your business. We find that most of our clients are in the professional services industries such as the legal sector and financial services, but we’re open to working with a range of businesses. It all starts with a conversation!

Modern Work Solutions​

We help businesses like yours to integrate their tools and channels together, unifying communication and collaboration, and offering remote working capabilities. Designed to boost productivity, drive efficiency, and streamline how your business operates, our modern work solutions help you to get ahead and enjoy smoother sailing.

IT Projects

Whether it's office moves, server migrations, or implementing and integrating systems, you can tap into our expertise to deliver successful IT projects that deliver on-time, and in-budget. We take a careful and stakeholder focused approach to design and implement projects that are smooth, secure, and able to deliver the best benefit to your team.

3CX Phone Systems

3CX Phone Systems

For businesses looking to unify and streamline their telephony, 3CX phone systems are a cost-effective solution. 3CX is easy to manage, offer low annual costs, advanced contact center features, as well as integrations with SMS, Whatsapp, MS365, and Google Workspace, making it a versatile telephony and communications solution.

Microsoft Azure

We offer end-to-end Azure hosting solutions for businesses. Bring your hosting into the Azure cloud, manage and scale databases easily, optimize the costs and performance of your digital services, support secure hybrid working, and much more, by using the full power and flexibility of the cloud.

Our Technology Partners

What SkySail Clients are saying…

Chances Client 2

“SkySail Technologies manages and monitors our entire network and provides our servers for 45+ users. Darren and his team have also provided our team with the education on security and data management. Working with SkySail allows us to keep our business growing and expanding.”

Stan Walt

Chances Kelowna

Pihl Law For Client Testimonial

“Partnering with SkySail Technologies helps us minimize our down time, increase our productivity and proactively manage external threats. SkySail Technologies helps us deliver good service to our clients and for that we’re grateful.”

Andrea Krause

Pihl Law Corp

Gillespie Lawyers Client Logo

“It has been our experience that the team at SkySail was very thorough in their assessment of our IT situation and needs; both for the immediate and the-future needs. They are very respectful that we don’t know a lot about IT which shows in how they interact with us and in their recommendations.”

Mark A. Bartle

Gillepsie Lawyers

Are You Ready to Set Sail?

Here to Help With Your Tech Challenges: Book an Insights Session With Us.

In a tech-tangle? Have a question? Have a goal in mind, but unsure of how technology can help? We’ll be glad to meet you and have a conversation.

Book a no-obligation insights session with us today, we’ll listen closely to you, and provide impartial guidance that provides actionable insights that help you to get to where you’d like to be.