Customer Success Operations Specialist

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 Customer Success the operating system for our post‑sale teams. You will take strategic direction and solution blueprints from the Senior Manager, Success Operations, and build, test, and release high‑quality configurations and automations to the Success organization. Partnering across Support, CS, and RevOps, you’ll orchestrate clean data flows from Zendesk and HubSpot into Gainsight CS (Rules Engine, Data Designer, Journey Orchestrator, Scorecards, Success Plans) so routine work is automated, risky work is reviewed, and every teammate has trustworthy context at their fingertips.

Responsibilities

Get ready to go beyond order-taking. Your strategic responsibilities include:

Gainsight CS first: Administer and enhance Data Designer, Rules Engine, Scorecards, Success Plans, and Journey Orchestrator as first‑class products that drive proactive customer outcomes.

Build from blueprints: Translate strategic designs from the Senior Manager into executable solutions; produce build docs, test plans, and release notes; manage change control.

Support→CS integration: Pipe Zendesk signals (intent, sentiment, language, priority) into Gainsight objects; auto‑create CTAs/Success Plans with human review thresholds.

Zendesk operations: Maintain triggers/automations, macros, views, SLAs, and dashboards; implement AI‑assisted triage and suggested replies with clear rollback paths.

Quality & governance: Define data contracts and schema validations; set up lineage and monitoring (freshness, accuracy, latency), access controls, and PII redaction.

Testing & evaluation: Run A/B tests and offline LLM evals; gate releases behind success criteria; maintain incident playbooks and audit trails.

Measurement: Instrument ROI for every flow (time saved, deflection, CSAT, NRR influence) and publish actionable dashboards for stakeholders.

Enablement & intake: Document “why & how,” deliver training, manage request intake, and keep a transparent backlog prioritized by impact and risk.

Your Strengths and Skills

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 experience (required):

 Gainsight CS (2+ years) administering Rules Engine, Data Designer, Journey Orchestrator, Scorecards, Success Plans in a SaaS environment. 

Zendesk (2+ years) in admin/operations: triggers, automations, views, macros, SLAs; experience with AI features (triage/suggested replies) is a plus.

Additionally valued: 

Hands‑on integrations across Zendesk ↔ Gainsight ↔ HubSpot using iPaaS (n8n/Workato/Tray/Make) or APIs/webhooks; basic scripting (Python/JavaScript/SQL).

 Practical LLM usage (ChatGPT/OpenAI or Google Gemini): prompt design, tool/function calling, offline/online evaluations, and safe launch practices.

 Strong debugging and observability habits (logs, metrics, alerts); governance mindset (permissions, PII redaction, incident response, rollback strategies). 

Clear communicator who versions prompts/flows, tests before deploy, and reports outcomes simply.

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.

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.