Base pay range$90,000.00/yr - $120,000.00/yrAdditional compensation typesCommissionDirect message the job poster from OrchestryCompany OverviewOrchestry is a remote-first SaaS company that helps organizations simplify governance, adoption, and growth within Microsoft 365. We believe great tools should empower people—not overwhelm them. As we scale, we’re looking for people who love autonomy, embrace thoughtful collaboration, and are excited by building alongside an early‑stage team.The OpportunityThe Customer SuccessTechnical Solutions Specialist(TSS) is a hybrid technical and customer-facing role that bridges onboarding, advanced troubleshooting, and solution design. You’ll own the technical aspects of customer onboarding, support managed evaluations during presales, create reusable integration assets, and help customers overcome complex configuration challenges. You’ll also partner with the presales team on technical discovery and proof-of-concepts. This role plays a critical part in accelerating customer time‑to‑value while strengthening internal knowledge sharing. If you’re passionate about Microsoft 365, APIs, automation, governance frameworks, and helping customers deploy solutions that just work, this role is your playground.What You’ll Be DoingCustomer Success, Technical Advocacy & EnablementOwn technical onboarding components includingAPI integrations, webhooks, Power Platform, Power BI, Azure Functions, and PnP provisioning .Participate in technical discovery to uncover integration, governance, and automation needs.Deliver technical enablement sessions for admins, architects, and technical SMEs.Advise customers on programmatic setups, governance approaches, automation best practices.Triaging advanced issues in collaboration with Product & Engineering; provide actionable reproduction steps and context.Support managed evaluations:



defining technical success criteria, validating configuration, reducing friction.Join discovery calls to understand tech requirements and translate them into solution approaches.Maintain prototypes inPower Automate, Power BI, Agents, Azure Functions, etc.Contribute to RFPs, proposals, and documentation including security/compliance responses.Maintain & optimize demo environments with rich, realistic data and advanced scenarios.Technical Support & Internal EnablementOwn advanced troubleshooting and reduce escalations to Product/Engineering.Perform intermediate debugging and root‑cause analysis.Maintain internal documentation, FAQs, and advanced troubleshooting playbooks.Create enablement pathways for CS, Sales, and Support teams.What You BringCore CompetenciesStrong technical understanding ofMicrosoft 365(SharePoint, Teams, Entra, Purview, Power Platform, Azure).Experience withPnP provisioning, APIs, webhooks, automation, scripting, and integration patterns .Ability to diagnose, debug, and resolve complex enterprise technical scenarios.Excellent communication skills for both technical and non-technical audiences.Ability to translate conceptual requirements into technical solutions and vice versa.Collaborative mindset — works smoothly with Product, Engineering,



Sales & CS.Preferred QualificationsProficiency withPowerShell / PnP PowerShellfor automation and enterprise provisioning.Experience integrating withMicrosoft Graph APIusing SDKs and best practices.Solid grasp ofgovernance/compliancerequirements and Purview configuration.Experience building analytics solutions inPower BIand workflows inPower Automate/Azure Functions .Ability to leverage AI development tools (ChatGPT, Claude) for code generation, debugging, and automation.How You'll Have ImpactReduced escalations to Product/Engineering.Faster onboarding completion for customers with complex setups.Improved advanced ticket resolution time.Higher presales conversion through stronger technical enablement.Increased availability of reusable technical assets across the org.Why You’ll Love Working HereRemote‑first culture with flexibility and autonomy.A truly beloved product with exceptional PMF.A collaborative environment that values curiosity and iteration.Competitive pay, equity, benefits, and perks.This role will be eligible to earn a variable compensation element in addition to base pay.The chance to shape how customers adopt and scale Orchestry’s platform.Compensation PackageOTE $110,000 - $130,000 CAD per annum100% remote work setup with schedule flexibilityComprehensive Benefits package in Canada includes additional mental health, HSA and more.Career development programs and home office allowanceRegular team offsites and swag, opportunities to connect both in person and via remote eventsInterview ProcessRecruiter screenMock CS Challenge or Work AssignmentFinal Leadership interviewApplicationInterested in joining Orchestry? We’d love to hear from you. Submit your application, resume, and a few lines about why this role excites you.ReferralsReferrals increase your chances of interviewing at Orchestry by 2x.Seniority levelMid‑Senior levelEmployment typeFull-timeJob functionInformation TechnologyIndustries: Software Development#J-18808-Ljbffr

📌 Technical Solutions Specialist - $90,000 - $120,000 A Year - Remote (Winnipeg)
🏢 Orchestry
📍 Winnipeg