Customer Success Operations Manager
Company shown to members 🔒 · Remote · Canada only
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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- 5+ years required
- Where you can live
- Canada only
- Skills and tools
- hubspot, forecasting, customer success, onboarding, churn, retention
- Job type
- Full-time
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Job details
- Where you can work
- Canada
- Employment type
- Full-time
- Advertised pay
- CA$116K/yr
- Experience
- 5+ years required
- Employer publication date
- 4 September 2026
- First recorded by Psst
- 12 October 2026
- Last checked at the source
- 10 November 2026
About the job
Spellbook is the most comprehensive AI copilot for transactional lawyers. It works directly inside Microsoft Word to help legal teams draft, review, and negotiate contracts up to 10x faster and with greater precision. Today, more than 4,000 law firms, in-house teams, and solo practitioners rely on Spellbook to simplify their workflows and eliminate the drudgery of everyday contract work.
We are backed by leading investors including Khosla Ventures, Thomson Reuters Ventures, Inovia Capital, The LegalTech Fund, Bling Capital, and Moxxie Ventures. The company recently raised $50 million in Series B funding, led by Keith Rabois at Khosla Ventures, bringing its total funding to more than $80 million.
*This is an existing vacancy
ABOUT THE ROLE
Customer Success Operations Manager has one job: make all GTM teams measurably better. We do that by giving leadership numbers they can plan against, giving front line CSMs and sales reps systems that absorb the administrative work, and designing the business processes that will enable us to scale efficiently.
This is the first dedicated Post Sales Operations role at Spellbook, so you will be defining the function. Your role covers reporting, forecasting, tooling, org design, and standing up new post sale processes. You will partner directly with CS leadership to find friction and remove it, and work cross-functionally with other GTM teams to ensure CS strategy and execution ladders up to company level goals.
WHO YOU ARE
To succeed here you need to be a builder. Someone who creates structure out of ambiguity, turns a high-level goal into a working process that CS adopts. In partnership with CS and Revops, you will build a prioritization roadmap to help us continue to scale.
The right candidate will balance a systems mindset with sharp operational instinct and business acumen. You are comfortable setting the strategy, running the project, and going deep on the technical work when needed.
RESPONSIBILITIES
- Building the reporting layer CS runs on: Owning post-sale reporting end to end — NRR and GRR, logo and dollar churn, expansion pipeline, time-to-value, seat activation, adoption, and CSM capacity and coverage. Then going past the dashboard: surfacing at-risk cohorts, adoption gaps, and segment-level patterns early enough that someone can act on them.
- Owning renewal and churn forecasting: Building a renewal forecast accurate enough to plan against, and the risk scoring underneath it. You will build the early warning signals and attach a defined play to every signal so it produces actions.
- Engineering the CS tech stack: Owning post-sale systems from evaluation through selecting, implementing, adoption, and administering a Customer Success platform (Vitally and Hubspot). You will also own the post-sale data model: account hierarchy, seats and licenses, lifecycle stages, and contract and renewal data.
- Enabling new business processes: Designing operating models for motions we either don't have yet or run informally today such as segmentation and coverage, onboarding, QBRs, renewals, expansion, escalation, and save motions.
- Connecting the dots across teams: Leading the connective-tissue projects that span functions such as the sales-to-CS handoff, CS-to-support escalation, the CS-to-product feedback loop, and the data plumbing between them.
QUALIFICATIONS
- Relevant experience: 5+ years in Customer Success Operations, Revenue Operations, or GTM Systems at B2B software companies, including at least one environment where you built the function rather than maintained an existing one.
- Post-sale tooling experience: Business admin or technical admin of a Customer Success platform.
- Reporting and forecasting depth: Fluent CRM reporting and comfortable with BI tools (Omni).
- Post-sale business context: Strong business acumen and a working understanding of the metrics that run a post-sales organization such as NRR, GRR, churn, expansion, time-to-value, adoption, and capacity planning.
- Scale-first mindset: You are process-curious and efficiency-obsessed, with real experience redesigning processes and using AI tools (LLMs, agents, automation) to reduce administrative burden.
- Ability to move a customer-facing team: You have gotten CSMs or a similar team to adopt something new without having authority over them.
- Excellent organization and project management: You create and maintain detailed project plans, hit tight deadlines, and surface risks and issues before they land.
- Excellent written and verbal communication: You can work through a workflow detail with an individual CSM and present a retention picture to the executive team on the same day.
- Independence and conscious collaboration: Strong ability to work autonomously while pulling in the teams needed to land the outcome.
WHY JOIN SPELLBOOK?
- Embrace autonomy and accountability in a flexible work environment; we focus on outcomes and empower you to determine how to get the job done
- Access our company-paid group benefits for you and your family, with $1,000 towards mental health support
- Disconnect during our holiday closure and take advantage of our generous time off policies throughout the year
- Enjoy monthly paid meals, an annual wellness allowance to support your well-being and parental leave top-ups as your family grows
- Secure your stake in our success; you’ll receive competitive stock option grants as a pivotal early employee
INCLUSIVE HIRING AT SPELLBOOK
We are committed to creating an inclusive and supportive candidate experience. Should you require any accommodation whatsoever during the interview process, please inform us without any hesitation. Spellbook is dedicated to ensuring equal treatment and opportunity in all phases of recruitment, selection, and employment, in compliance with employment law. We do not discriminate based on gender, race, religion, national origin, ethnicity, disability, gender identity/expression, sexual orientation, veteran or military status, or any other protected category. Spellbook is proud to be an equal opportunity employer, fostering a culture of inclusivity and maintaining a work environment that is free from discrimination, harassment, and retaliation.
USE OF ARTIFICIAL INTELLIGENCE IN RECRUITMENT
Spellbook uses artificial intelligence (AI) responsibly to support administrative and efficiency-focused aspects of our recruitment process. This includes activities such as drafting job descriptions, generating interview questions, note-taking and recordings, and supporting sourcing and scheduling workflows. All candidate evaluations, interviews, and hiring decisions are made by members of the Spellbook team. While AI tools may assist with screening and assessment, they do not replace human judgment in selection decisions. Our use of AI is intended to streamline routine tasks, improve consistency, and enhance the overall candidate experience. We are committed to upholding principles of fairness, transparency, and accountability in all hiring activities. Spellbook regularly reviews its recruitment practices to mitigate bias and to ensure alignment with applicable laws and evolving best practices.
OUR COMPENSATION PHILOSOPHY
Spellbook uses industry benchmark data to establish compensation bands for all roles. The salary range listed for a position reflects the expected total wage range for the role—including base salary and on-target commissions, where applicable—and may span multiple career levels. Final compensation is determined during the interview process based on factors such as experience, skills, scope, and role level. In addition to base salary and applicable commissions, total rewards may include equity, health and wellness benefits, and other company programs. Full details will be shared during the interview process.
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