Customer Success Operations Specialist (Gainsight Administrator)

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 Great 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 Specialist, 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.
• Build the integrations that feed the stack — CRM ↔ Gainsight, Zendesk → Gainsight, and the Databricks data flows — to the integration strategy CS Ops leadership agrees with RevOps and the data team.
• Extend the platform where native features run out: API-based workflows, n8n automations, and AI-assisted scripting.
• Protect system integrity: say what's technically possible, push back on hacks that create tech debt or ungoverned fields, and propose the durable version instead. We'd rather hear "not like that, but here's how" than get a workaround.

• Own the release: sandbox testing, cutover, data validation, and a rollback plan you'd actually be willing to use.
• Own the documentation that ships with every launch — what changed, how it works, and what to do when it doesn't — alongside the standing system documentation: configurations, data dictionaries, and integration maps. Process documentation stays with the teams who run the process; you make sure the technical picture behind it is accurate.
• Partner with the Senior Manager, CS Operations and our Enablement team on launch training: you bring the substance and the walkthrough, they run the room.
• Watch the weeks after go-live, not just the go-live: monitor programs and data in production, and close the loop on what needs fixing.

• First line for "the system is broken" and "the data looks wrong": diagnose to root cause, apply a permanent fix, and document what happened.
• Own the ongoing health of the integrations and syncs — catch failures before stakeholders do, and own data hygiene across the CS stack.
• Maintain the support-data layer in Gainsight — ticket signals, sentiment, priority, volume — and the datasets the wider team builds on.
• Own the AI layer of the stack: data readiness, agent configuration and maintenance, platform AI features, and the guardrails around them.
• Turn around small field-level asks quickly — a missing field, a filter change — where they sit inside a project that's already approved. New work arrives scoped and prioritized through CS Ops intake; requests that land on you directly get routed there rather than quietly absorbed.
  

What we’re looking for

We care about what you can do more than where you’ve done it. However, experience in the following areas will help you hit the ground running in this role:

Must-have

• Gainsight CS — 2+ years hands-on administration in a SaaS environment: Rules Engine, Data Designer, Journey Orchestrator, Scorecards, Success Plans, CTAs and playbooks. Gainsight certification is a plus 
• Demonstrated ability to take a scoped project and deliver it independently — estimating realistically, testing before deploy, and flagging risk early rather than at the deadline.
• Working knowledge of APIs, data mapping, and SQL; comfort reasoning about data structures and joins.
• Experience integrating multiple systems — CRM, support, and data warehouse — and debugging when they disagree. Our CRM is HubSpot; Salesforce integration experience transfers directly and we don't expect prior HubSpot exposure.
• Strong troubleshooting instincts: you enjoy untangling data discrepancies and tracing behaviour to a root cause rather than patching symptoms.
• Comfort gathering requirements directly from the people who'll use the thing — asking the questions that surface what they actually need, not just what they asked for.
• Clear written communication and documentation habits. You can explain a technical constraint to a non-technical stakeholder without losing them or oversimplifying.

Additionally valued

• Zendesk familiarity — the support integration and support datasets sit with this role, and admin-level Zendesk experience (triggers, automations, views, macros, SLAs) is a bonus rather than a requirement.
• Databricks, Snowflake, or comparable data warehouse experience, and comfort with SQL against it.
• iPaaS and scripting: n8n, Workato, Make, Tray.io; Python or JavaScript.
• Practical AI usage in an ops context — agents, prompt design, human-in-the-loop design, and evaluating output quality before trusting it.
• Governance mindset: permissions, PII handling, change control, incident response, rollback strategies.
  

Perks

ScalePad offers our employees a blend of purpose, growth, and genuinely great perks.

• Everyone’s an owner. Share in our success through our Employee Stock Ownership Plan (ESOP) and RRSP matching.
• Support for growing families. Parental leave programs are in place to support you and your family when it matters most.
• Structured mentorship with builders. Join opt-in mentorship programs and learn directly from founders and senior leaders who’ve scaled multiple SaaS ventures and spent decades in the MSP industry.
• Invest in your growth every year. Access an annual professional development budget to level up your skills, your career, and your impact.
• Set yourself up with great tools. Work with brand new, top-of-the-line hardware and equipment so you can do your best work, whether you’re at home or in one of our hubs.
• Modern ways of working. Roles at ScalePad are structured as remote or hybrid, with hub locations in Vancouver, Toronto, Montreal, and Phoenix. Specific work models are outlined in each posting.
• Support for hybrid life. Receive a monthly stipend to help you create an effective hybrid or remote work environment.
• Well-being and time to recharge. Take care of yourself with 100% employer-paid benefits.
  

Before You Apply

This is a full-time role for those who are eligible to work in Canada or the United States. We thank all applicants for taking the time to apply, but only candidates who make it to the next stage will be contacted.

Note on AI Use: ScalePad uses AI technology to support certain administrative aspects of our hiring process, such as transcription, note-taking, and interview documentation. These tools are strictly used to assist our team and have no influence on candidate evaluation or hiring decisions.

No recruiters, please.