Customer Success Operations Analyst

The Role Do you want to work at a high-growth company where your impact is seen and rewarded? Are you looking for the autonomy to do your best work? We are seeking a Customer Success Operations Analyst to accelerate revenue growth and enable us to scale. This role will report to the Customer Success Operations Manager. As a member of the Revenue Operations team, you will take ownership of critical systems and processes that power our Go-To-Market strategy, with a particular focus on our Customer Success platform and quoting workflows. This is a role for someone who thrives on solving complex problems independently, isn't afraid to dive deep into unfamiliar systems, and takes pride in building things the right way. You'll often be the subject matter expert in the room—and that's exactly how we want it. What you'll be doing Serve as the primary point of contact for CPQ (Configure-Price-Quote) support on the CS side—troubleshooting quoting issues, managing cases promptly, and ensuring a seamless quote-to-cash process Own and execute a comprehensive Gainsight overhaul —audit, debug, and rearchitect our Customer Success platform to align with customer journey best practices and drive adoption, renewal, and expansion outcomes Build and maintain lifecycle processes, playbooks, and automation rules in Gainsight that support customer outcomes and business growth Assist with end-of-quarter CS compensation reports and audit process Create and coordinate key reporting for leadership, translating data and insights into executive dashboards on customer adoption, renewals, expansions, and churn Partner with Product and Data teams on usage analytics initiatives to provide visibility into customer health and inform the adoption journey Support internal change management activities for standard processes and tools across customer-facing teams Understand and prioritize the needs of Customer Success, Support, Onboarding, and Customer Marketing teams to inform a cohesive operational strategy Qualifications Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every qualification. At Affinity, we are dedicated to building a diverse, inclusive, and authentic workplace, so if you're excited about this role but your past experience doesn't perfectly align with the qualifications above, we encourage you to apply anyway. You may be just the right candidate for this or other roles. Required 2–5 years of experience in Revenue Operations, Customer Success Operations, or Sales Operations at a high-growth B2B SaaS company Gainsight admin experience —you've built and maintained rules, playbooks, CTAs, and dashboards, and you understand how to architect a CS platform that actually works Salesforce experience —comfortable navigating reports, dashboards, and data structures; you understand how Salesforce and Gainsight work together Experience with CPQ or quoting tools (e.g., Salesforce CPQ, MonetizeNow, DealHub, or similar)—you can troubleshoot quoting issues and understand the quote-to-cash workflow Strong understanding of SaaS metrics (ARR, GRR, NRR, churn) and post-sale finance terminology (billing, revenue recognition, renewals) Expert Excel/Google Sheets skills, including experience manipulating large datasets Self-starter mentality —you're resourceful, take initiative, and are comfortable figuring things out independently. You don't wait for answers; you find them. Comfortable operating in a fast-paced environment with evolving priorities and ambiguity Strong attention to detail and project management skills Nice to have Gainsight Admin Certification Experience with MonetizeNow specifically Familiarity with BI tools like Looker, Tableau, or Amplitude Experience in the CRM, data services, or private capital/financial services space Work Location: Remote or Toronto, Canada For those located in Toronto, for this role we're embracing a hub-hybrid ... (truncated, view full listing at source)