Careers An olympic-level team building the infrastructure that powers agreements worldwide Explore Open Roles

“There’s a great Canadian tech success story being written here in real time and I’m thrilled to be a part of it!” Walt Nathaniel Account Executive

We have a beginner's mind We stay open-minded and rethink things from first principles. We question assumptions and approach problems with curiosity, not ego.

We play to win Winning matters. We focus on outcomes, not optics. We do what works — and we move on.

We create energy We work hard and lift each other up. We bring positivity, momentum, and generosity to the team.

We find the magic We strive to be great, not good. We iterate until every part of our customer journey feels like magic.

We move with urgency Speed is a feature. We prioritize ruthlessly and ask, “Can we do this today?”

We're customer-obsessed We talk to customers, learn how they speak and think, and build for their reality — not our assumptions.

Open Roles Join the Spellbook team Manager, Mid-Market Customer Success Location Remote - Canada

Employment Type Full time

Location Type Remote

Department Customer Success

Compensation On Target Earnings CA$130K – CA$152K

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 We’re hiring a Manager, Customer Success to lead, coach, and scale a growing team of Mid-Market Customer Success Managers (CSMs) responsible for the full customer lifecycle from onboarding and adoption to renewals. This role is critical to helping the team operate consistently as we grow, while delivering strong customer outcomes.

You’ll initially manage a team of ~8 CSMs, with a clear expectation to hire and scale the team quickly. You will build the processes, playbooks, and reporting structures that enable CSMs to succeed at scale. This is a hands‑on role for someone who thrives in a fast‑paced, distributed startup environment and genuinely enjoys coaching and developing teammates.

RESPONSIBILITIES

Lead, coach, and support a growing team of Mid-Market CSMs across onboarding, adoption, and renewals

Hold weekly 1:1s focused on performance, account strategy, skill development, and career growth

Run bi-weekly call coaching sessions, emphasizing discovery, stakeholder management, value-based conversations, and renewal readiness

Join customer calls when needed to support escalations and model strong customer conversations

Foster a human‑first, low-ego culture built on trust, accountability, and continuous improvement

Drive strong portfolio outcomes across your team’s book

Oversee renewals end-to-end, ensuring proactive renewal motions and accurate forecasting

Help CSMs identify risk early, manage difficult renewals,



and navigate complex customer situations

Escalate renewal risks and systemic challenges to the Director of CS with clear context and recommendations

Partner closely with the Director of CS to design, implement, and refine:

Onboarding frameworks and ramp milestones

Adoption and account health playbooks

Renewal and forecasting workflows

Escalation paths and internal operating cadence

Ensure CSMs have the tools, clarity, and resources needed to deliver consistently as the team scales

Lead significant hiring efforts as the team grows, including interviewing and selection

Build and continuously improve onboarding and ramp plans so new CSMs reach productivity quickly

Provide hands‑on support to new hires during the ramp‑up to set a strong foundation

Monitor account health and adoption signals across the team’s portfolio

Operate with a high bar for clear, consistent communication in a distributed workplace

Collaborate closely with Account Management, Sales, Product, and Support to deliver a seamless customer experience

QUALIFICATIONS

2+ years of experience managing Customer Success teams in a high‑growth SaaS environment

Experience managing and scaling teams (from 5 to 10+ CSMs)

Proven success driving renewals, retention, and adoption outcomes

Experience hiring, onboarding, and ramping CSMs quickly

Strong understanding of proactive adoption strategies and customer health management

Strong sales acumen or prior sales experience, with the ability to coach discovery and renewal conversations

Exceptional coach and people leader who invests in the growth of their team

Organized, data‑driven, and comfortable with forecasting and prioritization

Low‑ego, collaborative, and willing to roll up your sleeves to help the team succeed

Clear communicator who thrives in a fast‑paced, remote‑first environment

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.

Compensation Range: CA$130K - CA$152K

Perks &Benefits; Flexibility & Ownership Embrace autonomy and accountability in a flexible, distributed work environment. We focus on outcomes and trust you to determine how to get there.

Health & Well-Being Company‑paid group benefits for you and your family, plus $1,000 per year for mental health support (varies by location).

Time to Recharge Disconnect during our holiday closure and take advantage of our generous time off policies throughout the year

Growth & Life Support Annual wellness allowance, monthly paid meals, and parental leave top-ups as your family grows (varies by location).

Ownership Competitive salary and meaningful stock option grants — you’ll share in the success you help create.

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📌 Manager, Mid-Market Customer Success (Winnipeg)
🏢 Spellbook
📍 Winnipeg