✨ About Orchestry

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.
• Create reusable assets: integration guides, scripts, diagrams, API examples, architecture patterns .
• 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.

Presales Support

• Join discovery calls to understand tech requirements and translate them into solution approaches.
• Configure POC environments demonstrating Orchestry’s advanced capabilities.
• 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.
• Create presales enablement: diagrams, integration patterns, competitive technical differentiators .

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 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 & Benefits

We offer a competitive total compensation package aligned to our location & phase of growth, including:

• 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

📝 Application Process

Our interview process is friendly, transparent, and designed to help both sides learn. It typically includes:

1. Recruiter screen
2. Hiring manager interview
3. Peer Interviews
4. Mock CS Challenge or Work Assignment
5. Final Leadership interview

We aim to wrap our process within ~4-6 weeks, depending on schedules.

🙌 Apply Now

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.