Customer Success Operations Specialist

We're Hiring!

We're looking for brilliant thinkers to join our #Rocketeers. If you've ever wondered what it's like to work in a place where people enjoy their work and where talent is more important than the title, then keep reading.

What is ScalePad?

ScalePad is a market-leading software-as-a-service (SaaS) company with headquarters in Vancouver, Toronto, Montreal and Phoenix, AZ. However, we are proud to say our employee reach is now global so we can best serve our partners all over the world.

Our success is no accident: ScalePad provides MSPs of every size with the knowledge, technology, and community they need to deliver increased client value while navigating the continuously changing terrain of the IT landscape. With a suite of integrated products that automate and standardize MSP’s operations, analyze and uncover new opportunities, and expand value to clients, ScalePad is equipping the MSP adventure.

ScalePad has received awards such as MSP Today’s Product of the Year, G2’s 2024 Fastest Growing Product, and 2024 Best IT Management Product. In 2023, it was named a Best Workplace in Canada by Great Place to Work™. ScalePad is a privately held company serving over 12,000 MSPs across the globe.

You can contribute to our innovation and appreciate how your work is helping take this company to a higher level of operational maturity. More on that here.

Your mission should you choose to accept it.
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.

• 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.

Qualifications.

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.

What You’ll Love Working As A Rocketeer:

• Everyone’s an Owner: Through our Employee Stock Option Plan (ESOP), each team member has a stake in our success. As we scale, your contributions directly shape our future – and you share in the rewards.
• Growth, Longevity and Stability: Benefit from insights and training from our leadership and founder, whose extensive experience in funding and scaling successful software companies creates a stable environment for your long-term career growth. Their proven track record fosters a culture of lasting success.
• Annual Training & Development: Every employee receives an annual budget for professional development, empowering you to advance your skills and career on your terms.
• Hybrid Flexibility: Enjoy a world-class office at our headquarters in downtown Vancouver, Toronto, and Montreal
• Cutting-Edge Gear: Whether in the office or at home, you’ll be set up for success with top-of-the-line hardware.
• Wellness at Work: Our Vancouver office features a fitness facility, outdoor ping-pong tables
• Comprehensive Benefits: We’ve got you covered with an extensive benefits package with 100% medical and dental coverage fully employer-paid, RRSP matching after one year of employment, and even a monthly stipend to help offset the costs of the hybrid experience.
• Flexible Time Off: With our unlimited flex-time policy in addition to all accrued vacation allows you to take the time you need to recharge and thrive.

Dream jobs don’t knock on your door every day.  

ScalePad is not your typical software company. When we hire you, we aren’t just offering you a job, but rather we are committing to investing in both you and your long-term career. You'll help shape how this modern SaaS company operates and make a genuine impact on the future of our people, product, and partners.

We invite all qualified candidates to apply. Please note, you must be eligible to work in Canada to be considered for this role. We thank you for your interest. However, only successful applicants will be contacted.

At ScalePad, we believe in the power of Diversity, Equity, Inclusion, and Belonging (DEIB) to drive innovation, collaboration, and success. We are committed to fostering a workplace where every individual's unique experiences and perspectives are valued, and where employees from all backgrounds can thrive. Our dedication to DEIB is woven into the fabric of our culture, guiding our actions and decisions as we build a stronger and more inclusive future together.

Join us and be part of a team that celebrates differences, embraces fairness, and ensures that everyone has an equal opportunity to contribute and grow. Together, we're creating an environment where diverse voices are not only heard but also amplified, where everyone feels valued, and where we can all achieve our full potential.

Please no recruiters or phone calls.