Enterprise Customer Success Manager

Department: Customer Success

Location: Remote - Canada

Compensation: CA$123K – CA$145K

Employment Type: FullTime

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

Were looking for an experienced and highly organized Enterprise Customer Success Manager (CSM) to support our largest and most complex customers. This role is ideal for someone who thrives in fast-paced, evolving environments and is passionate about delivering value through structured onboarding, proactive account management, and executive-level communication. You’ll be a strategic partner to enterprise clients, driving adoption, managing layered stakeholder relationships, and ensuring long-term success with Spellbook.

RESPONSIBILITIES

• Own a portfolio of enterprise accounts, ensuring 97%+ gross revenue retention (GRR).

• Lead complex, multi-phase onboarding projects with enterprise clients, aligning timelines, deliverables, and key milestones across internal and client teams.

• Conduct discovery to deeply understand each customer’s legal workflows and business goals, tailoring onboarding and training accordingly.

• Develop and execute customized enablement strategies that support scalable adoption across large, layered organizations.

• Build and maintain strong relationships with multiple stakeholders, including senior legal and executive leaders.

• Run Quarterly Business Reviews (QBRs), demonstrating clear ROI and identifying opportunities for expansion or deeper platform engagement.

• Maintain accurate, up-to-date records in HubSpot and hold yourself to high standards of CRM data hygiene.

• Anticipate client needs and risks, proactively resolving issues and escalating when appropriate.

• Collaborate with product, engineering, and support teams to advocate for enterprise customer needs and improve the overall journey.

• Support renewals by driving usage, demonstrating value, and identifying champions within each organization.

• Stay agile in a fast-changing environment—refining playbooks, processes, and approaches to meet the evolving needs of enterprise clients.

• This role will support large global customers that may have team members outside of the EST timezone. Occasional meetings outside of standard working hours may be required to support these customers.

• Support with other responsibilities and projects as required.

QUALIFICATIONS

• 3+ years of experience in customer success, account management, or consulting, preferably in a B2B SaaS environment.

• Demonstrated success managing complex enterprise accounts with multiple stakeholders.

• Experience running structured onboarding projects and ensuring successful implementation.

• Polished communicator comfortable interfacing with C-level executives and legal professionals.

• Highly organized with strong project management skills; able to manage multiple moving pieces and meet deadlines.

• Comfortable with change and ambiguity—this role requires someone who can iterate quickly as we refine our enterprise journey.

• Strong analytical skills; able to interpret usage data to uncover insights and drive adoption.

• Proficient with HubSpot or similar CRM systems, with a commitment to maintaining clean, reliable data.

• Self-starter with a proactive mindset and strong sense of ownership.

NICE TO HAVES

• Experience in legal tech or working with legal teams.

• Familiarity with tools like MixPanel and customer success platforms (e.g., Vitally, ChurnZero, etc.).

• Training in consultative sales methodologies (e.g., Sandler, MEDDIC).

• Prior involvement in refining or building customer success processes from the ground up.

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.