Who We're Looking For At ScalePad, we hire thoughtful builders who want their work to matter. Our roles are designed for people who thrive on driving impact, see ambiguity as an opportunity, and believe that raising the bar is a team sport.

We don't bring people in to run playbooks. We hire people who want to rewrite them. And in this role, you'll get to do that, while shaping the future of managed services for our global partners. (That's what we call our customers.)

What is ScalePad At ScalePad, we're building more than software; we're building confidence and clarity for the people who manage the technology businesses rely on every day.

Our mission: help MSPs evolve into MVPs (their clients' most valuable partner). Our tools turn them from reactive service providers into strategic advisors through a consistent, scalable Customer Success motion.

Our product suite unifies risk insights, client planning, and service delivery so MSPs can have smarter conversations, show clients their value, and grow their revenue.

But our purpose goes beyond our software. We're creating a workplace where curious, growth-minded people can do their best work, where ideas are valued, progress is shared, and everyone belongs. Together, we're creating a future where MSPs don't just keep businesses running, they help them thrive. We believe that when our partners succeed, we all do.

With offices in Vancouver, Toronto, Montreal, and Phoenix and a global-first mindset. ScalePad has grown into a category leader trusted by 12,000+ partners across 60+ countries.



We've been recognized for our products and corporate culture by MSP Today, G2, and Excellent Place to Work™, to name a few.

About The Role Make Gainsight the trusted operating system that drives our post sales success As our Customer Success Operations Manager, you'll own the hands-on delivery of Gainsight CS across Customer Success, Onboarding / Professional Services, and Support. . This is a builder's role within our broader Revenue Operations organization, working directly with the CS Operations Lead to turn prioritized business needs into solutions that scale.

You'll work deeply in Gainsight - Rules Engine, Data Designer, Journey Orchestrator, Scorecards, Success Plans, CTAs, and playbooks - while keeping data flowing reliably across HubSpot, Zendesk, and Databricks. You'll also extend our stack through APIs, n8n, and AI-assisted automation.

When something doesn't look right, you're the person who gets under the hood, finds the root cause, and fixes it for good.

If you love turning business problems into thoughtful technical solutions and seeing what you build directly improves how customer-facing teams work, you'll thrive here.

What You'll Own Get ready to go beyond order-taking. Your strategic responsibilities include:





Take a validated, prioritized requirement and decide the technical approach: gather the detail from the functional team, choose the approach, and recommend the build inside the target-state architecture.

Draft the technical design - tables, rules, data flows, trigger logic - for the Senior Manager to approve. Everything inside the existing architecture is yours to design and ship; architecture changes, new objects, and large modifications go through change-management review together.

Be the technical voice in scoping and discovery sessions: feasibility, effort, options and risks, so decisions get made with the real constraints on the table.

Estimate and phase realistically, and raise risks and blockers early rather than at the deadline.

Own Gainsight CS configuration end to end: Rules Engine, Data Designer, CTAs and playbooks, health scores and scorecards, Success Plans, layouts, and platform upgrades.

Build and maintain Journey Orchestrator programs - outbound journeys, email templates, audiences, triggers, and frequency guardrails.

Configure playbook content and CTA trigger criteria so every signal has an owner and an expected action.

Own the reports and dashboards the CS org runs on day to day, including what belongs on them: dashboards that tell a rep or a team lead where to spend their time, not everything we happen to have data for. You supply the numbers behind leadership's adoption and outcome reporting; you don't carry that narrative.

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📌 Customer Success Operations Specialist (Gainsight Administrator) (Winnipeg)
🏢 ScalePad
📍 Winnipeg