Chief of Staff

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.

We’re looking for a strategic, analytical, and highly organized Chief of Staff to partner directly with the CEO, COO, and executive team. This person will act as the connective tissue across the company—driving operational excellence, managing key business initiatives, and ensuring leadership has the data, insights, and alignment needed to execute effectively.

The ideal candidate is equal parts strategist and operator: comfortable rolling up their sleeves to build dashboards and board decks one day, and facilitating exec alignment or leading cross-functional projects the next.

• Oversee high-impact, cross-functional projects—from strategic initiatives to operational improvements.

• Ensure coordination between teams on critical priorities (e.g. product launches, process scaling, customer insights).

• Track deliverables and outcomes to ensure initiatives are completed on time and with measurable results.

• Build and maintain business dashboards and analytics for leadership decision-making.

• Partner with GTM, Product, and Finance teams to ensure KPIs (e.g. growth, retention, efficiency metrics) are measured accurately.

• Identify opportunities to improve operational processes, systems, and data flows.

• Drive the company-wide OKR process: facilitate quarterly goal-setting, alignment, and progress tracking.

• Partner with leaders to define success metrics and ensure accountability through regular check-ins and reporting.

• Maintain visibility into key business priorities, proactively surfacing risks or opportunities to the leadership team.

• Own investor reporting and board deck construction—synthesizing company metrics, narrative, and visuals into clear, concise materials.

• Partner with Finance and Department Heads to ensure data accuracy and consistent storytelling.

• Support fundraising and investor relations by maintaining up-to-date company KPIs, benchmarks, and narratives.

• 5+ years of experience in strategy, operations, consulting, or analytics within a fast-growing SaaS or technology company.

• Proven track record of managing complex, cross-functional initiatives.

• Strong analytical and data visualization skills (e.g. Excel, Google Sheets, Metabase, Looker, or similar).

• Exceptional communication and storytelling ability—particularly in translating complex data into compelling narratives.

• Highly organized and comfortable working in ambiguity, with a bias toward action.

• Able to work in-office in Toronto 2–3 days per week.

• Experience with investor or board reporting.

• Exposure to FP&A or BizOps functions in a SaaS context.

• Familiarity with tools like HubSpot, Mixpanel, and Stripe.

• Previous founder

• 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

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.