Job Description

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 model, designed to balance flexibility with meaningful in-person collaboration. Team members within commuting distance are expected in-office 2–3 days per week, typically Tuesday through Thursday. We believe great things happen when people come together intentionally to connect, create, and build momentum as a team.

What you’ll enjoy at Affinity:

• We live our values: As owners, we take pride in everything we do. We embrace a growth mindset, engage in respectful candor, act as playmakers, and “taste the soup” by diving deep into experiences to create the best outcomes for our colleagues and clients.
• Health Benefits: We cover both you and your dependents’ extended health benefit premiums and offer flexible personal & sick days to support your well-being.
• Retirement Planning: We offer an RRSP plan to help you plan for your future.
• Learning & Development: We provide an annual education budget and a comprehensive L&D program.
• Wellness Support: We reimburse monthly for things like home internet, meals, and wellness memberships/equipment to support your overall health and happiness.
• Team Connection: Virtual team-building activities and socials to keep our team connected, because building strong relationships is key to succes.

A reasonable estimate of the current range is $68,000.00 – $85,000.00 CAD Base. Within the range, individual pay depends on various factors including geographical location and review of experience, knowledge, skills, abilities of the applicant.

About Affinity

With more than 3,000 customers worldwide and backed by some of Silicon Valley’s best firms, Affinity has raised $120M to empower dealmakers to find, manage, and close more deals. How? Our Relationship Intelligence platform uses the wealth of data exhaust from trillions of interactions between Investment Bankers, Venture Capitalists, Consultants, and other strategic dealmakers to deliver automated relationship insights that drive over 450,000 deals every month. We are are proud to have received Inc. and Fortune Best Workplaces awards as well as to be Great Places to Work certified for the last 5 years running. Join us on our mission to make it possible for anyone to cultivate and fully harness their network to succeed.

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