Greg K.

I've been building MSP operations on ConnectWise across two IT services companies, with eight of those years as founding CEO and CSO of a fully managed IT services firm. I first implemented ConnectWise in 2008, migrating us off Request Tracker, and over time we used the full range of the PSA's capabilities: ticketing, billing, agreements, reselling IT products through QuoteWerks, and eventually employee time tracking, with the whole system synced to QuickBooks Desktop for billing and payroll. Our RMM evolved from LogMeIn to Kaseya to Continuum and finally to NinjaOne, each migration run as a managed parallel transition rather than a rip-and-replace. I've built incident response, disaster recovery plans and tested them with the client, led vulnerability assessments, and managed the full client base transition from break-fix to fully managed services, raising our Net Promoter Score from mid-80s to above 98%. I know what a well-run MSP looks like from the inside, and I have lived the costs and pain of a broken one. When I design an automation flow, audit trails and permission structures are in the first draft instead of bolted on as afterthoughts. The type of work I do now applies the same discipline to MSP operations specifically, and also to small business operations more broadly. It focuses on three things: mapping where current processes are breaking down and costing time or money, documenting the business logic carried in people's heads, and connecting existing tools so data flows without manual re-entry. The documentation I write can be understood by whoever owns the decision and followed by whoever does the work, without gaps and assumed knowledge. And because I fix the process before touching the software, you don't end up with expensive tools that speed up a broken or wasteful workflow. That same discipline applies to compliance work: I currently advise a technology company on SOC 2 Type 2 readiness as their policy and governance lead, authoring their control catalog and security policies and structuring the evidence their compliance platform produces for audit. That background shows up in results. Applying lean principles and low-touch automation reduced one firm's internal bookkeeping from 18 hours bi-weekly to under 3. Another engagement mapped two workflows for a field service business and identified nearly 7% of their annual revenue in recoverable labor waste that had been buried in their margins for years, visible only once someone traced the actual process end to end. If you or your team is manually re-entering data between systems, rebuilding context on every handoff, or depending on one person's memory or physical presence to keep a critical process running, the waste cost is already embedded in your numbers. It shows up as slow quote turnaround, invoicing delays, onboarding friction, project missteps, and capable people spending time on work a well-designed process would handle. Most business owners I work with want the same thing: a business that doesn't fall apart the moment they step away from it. I'm a native English speaker based in Manitoba, Canada (CST), with more than 26 years of history as a founder and operator across managed IT services, wireless broadband infrastructure, and operations consulting. Starting and scaling businesses from zero to a saleable asset gives a different vantage point than advising from the outside. Industries I've worked in include field service trades, custom road construction equipment manufacturing, national window and door manufacturing, multinational apparel and soft goods manufacturing, and residential construction; environments where a broken process doesn't show up as a line item. It shows up as margin that quietly slides down the drain. If you're looking for someone to fix a specific bottleneck rather than run an open-ended engagement, review the project listings below. Each one has a defined scope, fixed fee, and clear deliverable. If your situation doesn't fit one of those exactly, send a message describing the constraint and I'll tell you honestly whether I can help you.