Base pay range $90,000.00/yr - $120,000.00/yr

Additional compensation types

Commission

Direct message the job poster from Orchestry

Company Overview Orchestry 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 Opportunity The Customer Success

Technical 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 Doing Customer Success, Technical Advocacy & Enablement

Own technical onboarding components including

API 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 in

Power 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 Enablement

Own 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 Bring Core Competencies

Strong technical understanding of

Microsoft 365

(SharePoint, Teams, Entra, Purview, Power Platform, Azure).

Experience with

PnP 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 Qualifications

Proficiency with

PowerShell / PnP PowerShell

for automation and enterprise provisioning.

Experience integrating with

Microsoft Graph API

using SDKs and best practices.

Solid grasp of

governance/compliance





requirements and Purview configuration.

Experience building analytics solutions in

Power BI

and workflows in

Power Automate/Azure Functions .

Ability to leverage AI development tools (ChatGPT, Claude) for code generation, debugging, and automation.

How You'll Have Impact

Reduced 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 Here

Remote‑first culture with flexibility and autonomy.

A truly beloved product with exceptional PMF.

A cooperative 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 Package

OTE $110,000 - $130,000 CAD per annum

100% remote work setup with schedule flexibility

Comprehensive Benefits package in Canada includes additional mental health, HSA and more.

Professional development programs and home office allowance

Regular team offsites and swag, opportunities to connect both in person and via remote events

Interview Process

Recruiter screen

Mock CS Challenge or Work Assignment

Final Leadership interview

Application Interested in joining Orchestry? We’d love to hear from you. Submit your application, resume, and a few lines about why this role excites you.

Referrals Referrals increase your chances of interviewing at Orchestry by 2x.

Seniority level Mid‑Senior level

Employment type Full-time

Job function Information Technology

Industries: Software Development

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📌 Technical Solutions Specialist (Winnipeg)
🏢 Orchestry
📍 Winnipeg