Helper Connectwise Jobs in Calgary, AB (NOW HIRING)

Lyra Technology Group is seeking a Director of Service to oversee all service delivery outcomes for a Managed Services Provider.  This role will ensure we deliver excellent, consistent client experience while scaling profitably through clear direction, strong people leadership, and data-driven operational execution.  The Director of Service owns the strategy, performance, and improvement of the service organization, supporting clients across multiple industries. You will lead through managers, build a metrics-driven culture, strengthen accountability, and ensure projects and managed services are delivered on time, on budget, and with high quality.  This role has significant autonomy across service operations, budget, tooling decisions, and performance management-escalating only decisions that create significant business-wide impact or require major financial commitment through the President/Integrator.

Your work as a Director of Service will include the following duties:  

Service Leadership & Culture
   Lead and coach the Service leadership team (including the Services Manager and Projects & Improvements Manager, or their successors).
   Create clarity across priorities, roles, and decision rights-reducing friction over shared resources.
   Build a culture of accountability, continuous improvement, and "Help First" client service.

Client Experience & Service Quality
   Drive consistent service delivery that improves CSAT, reduces escalations, and resolves issues with high-quality solutions.
   Establish a system for ticket trending and recurring-issue prevention (problem management mindset).
   Serve as an escalation resource as needed-primarily by ensuring the right people and processes engage quickly.

EOS Execution: Scorecard, Rhythm, and Accountability
   Own Service measurables and present Service performance in weekly Leadership Team (L10) meetings.
   Implement/maintain a service operating rhythm: scorecard cadence, weekly priorities, issue-solving, and accountability.
   Identify what additional KPIs The ITeam should track and implement them with discipline.

SLA Performance & Ticketing Discipline 
   Own SLA compliance and the underlying data integrity required to measure and improve it.
   Improve ticketing workflows and standards in ConnectWise so performance is reportable, accurate, and actionable.
   Ensure responsiveness standards are consistently met:
   Current Business hours: respond/pick up tickets within 4 hours (Mon-Fri) - live phone pick up with 15 minute to return a voicemail.
   After-hours: best-effort on-call responsiveness for calls.

Projects & Delivery Excellence
   Ensure project delivery is predictable and well-managed: scope, schedule, resourcing, execution, QA/closeout.
   Improve project management cadence and reduce "project starvation" caused by reactive demands.
   Resolve the structural question of "dedicated projects vs. shared resources" using data and capacity planning.

Capacity Planning & Org Scaling
   Build a capacity model that links ticket volume, SLA targets, and project demand to staffing needs.
   Reduce voicemail/call abandonment through improved triage, scheduling/dispatch, and resource allocation.
   Make hiring recommendations with clear ROI and workload justification.

Financial Ownership & Vendor/Tool Strategy
   Own the Service budget and be accountable for service and project gross margin.
   Improve labor efficiency, utilization/throughput, realization, overtime control, and forecasting.
   Lead vendor management and tool cost optimization across service delivery.

Cross-Functional Alignment
   Partner with Sales/Account Management (relationship owners) to ensure smooth onboarding, delivery expectations, and feedback loops.
   Coordinate with the President/Integrator on priorities that affect the whole business (major investments, strategic changes, significant hiring).

Measurables (Initial Weekly Scorecard Ownership)
   The Director of Service will own and mature the Service Scorecard. Initial weekly measurable ownership includes:
   SLA compliance
   Number of calls to voicemail (and/or abandonment rate as available)
   Number of escalations (with trend by tier/client)
   Projects over budget (and progression to on-time/on-budget/on-scope)
   Service team capacity (forecast vs. actual; coverage; workload vs. staffing)

Our ideal Director of Service has the following qualifications:
   Proven leadership experience in a service delivery organization; MSP/Managed IT Services leadership experience strongly preferred.
   Demonstrated ability to build and run a metrics-driven operation (scorecards, forecasting, performance management).
   Strong people leadership: coaching managers, developing teams, handling conflict, and driving accountability.
   Working knowledge of MSP service delivery (ticketing/SLA systems, escalations, documentation, and project delivery).
   Technical credibility sufficient to set standards, review architecture, and engage in escalations when needed (without being the day-to-day engineer).
   Strong written and verbal communication; client-focused decision-making.
   Proven strategic planning skills and experience
   Nice to have (not required): ITIL, PMP, HDI, CISSP, EOS experience.

The targeted base compensation for this role is 130,000 -150,000 CAD and will operate out of the Calgary, Alberta office on a hybrid basis. If you're motivated by meaningful client relationships, strategic selling, and a dynamic work environment-we want to hear from you.