Overseeing a company’s information technology and computer systems has evolved into a digital posture for your business requiring greater transparency between operational systems and customer experience. Technology leadership is an integral part of the management team and responsible for ensuring that digital tools and strategies are working to further the goals of the company. But what happens if you’re too small, too far behind, or under-resourced to hire a full-time CIO?



Free yourself from the burden of taking months to find a new CIO. Sidekick has 25 or more years of technology experience, most recently in a senior operating leadership transformative role. We can be on board in as little as 24 hours depending on your need. Sidekick acts as a dedicated member of your senior staff reporting directly to executive leadership, yet equipped with world-class processes and broad experience to benefit your organization.

Work anywhere


An effective digital posture is essential for today’s business environment. It affects both employee and customer experience and directly impacts Executive decision-making success. Hire a dedicated professional and expect outstanding results.

People make it work


What if you could fill your technology leadership slot immediately, in a matter of hours? What if you could guarantee that your new technology leader would be a true strategic business partner with more than 25 years of experience, and not just an IT-centric operational generalist? What if you never had to pay for search fees, employee benefits or severance? What if you had immediate access to a technology executive to help guide your team toward a new strategic direction?


Sidekick has served with private equity in C-suites and leadership roles in SMBs across the province, and in specialist roles with brands across the world. Unlike consulting firms, with Sidekick your service level is exactly what you need and you will never be subject to unnecessary fee expansion or lower-level resources. Best of all, we become your company’s CIO – a dedicated member of your senior staff reporting directly to executive leadership, yet equipped with world-class processes at the level of engagement your business needs.

Listen to Customers


  • Advise on cloud and storage strategies, establishing a reliable back-up and recovery system
  • Identify specific user needs and expectations
  • Meet regularly with senior management to discuss ongoing and future technological requirements
  • Negotiate and manage technology service agreements
  • Source the most appropriate hardware and software products for your system as part of a comprehensive asset management strategy
  • Manage service delivery throughout the organization
  • Safeguard data and the security of sensitive information, meeting all regulatory compliance requirements
  • Assume the role of project manager to attain specific objectives
  • Problem solve and provide the most effective solutions as issues arise, giving day-to-day user support throughout your organization
  • Implement new systems and train staff
  • Prepare budgets to accompany short, medium and long-term projections
  • Create a plan that will stay ahead of the ever-changing IT curve, ensuring business continuity and a seamless transition to emerging technologies


We serve SMB and private-equity owned organizations across all industries by placing world-class operational leadership in technology leadership roles (CIO) via innovative and compelling arrangements for operational leadership engagements:

  • Virtual – one to four hours per week with an open-ended timeframe in an advisory capacity
  • Fractional – 20-80% of full-time in an accountable role with an open-ended timeframe
  • Interim – full-time, short-term accountable role usually lasting 6-9 months
  • Retained – full-time, long-term role

You may also be engage Sidekick outside of an operational role in situational leadership to provide:

  • Opinion (existing or proposed technology assessment or due diligence for mergers and acquisitions)
  • Outcome (bankruptcy preparation, post-acquisition remediation, program or initiative turnaround, technology selection, etc.)

CIOaaS combines the best of leadership with the best of consulting.

Free yourself from the burden of taking 6-12 months to find a new technology leader. We can be on-board in as little as 24 hours.

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