Full-Time

Customer Support Specialist

Updated on 5/7/2026

Spellbook

Spellbook

51-200 employees

AI-powered contract drafting and review

Compensation Overview

CA$60k - CA$80k/yr

+ Stock Options

Remote in Canada

Remote

Category
Customer Experience & Support (1)
Requirements
  • 2+ years of experience in a technical support or customer support role.
  • Experience facilitating 1:1 and small group training sessions.
  • Proficiency with support tools such as Intercom and Slack.
  • Exceptional written and verbal communication skills.
  • Strong problem-solving skills with meticulous attention to detail.
  • Ability to stay calm, patient, and empathetic when assisting customers.
  • Experience with real-time customer interactions through email, calls, and chat.
  • Comfortable working in a fast-paced, dynamic startup environment.
  • A proactive approach to improving customer support processes.
Responsibilities
  • Respond to support tickets and live customer chats during business hours (Monday to Friday, 9 am to 5 pm), addressing customer inquiries and resolving technical issues with empathy and efficiency.
  • Book 1:1 calls for in-depth troubleshooting or refresher training, while promoting group webinars when appropriate.
  • Use your technical skills to independently resolve issues or collaborate with the Engineering team when needed.
  • Proactively identify patterns in customer feedback to recommend improvements to our product or support processes.
  • Occasionally run Zoom group training for customers and answer their questions in real-time.
  • Create and update Help Centre articles to ensure our customers have access to self-service resources.
  • Record and update how-to videos and other educational materials as the product evolves.
  • Other responsibilities as required.
Desired Qualifications
  • Experience in the legal or legal tech industry.
  • Familiarity with AI or SaaS products.
  • Previous experience creating customer-facing documentation or video tutorials.

Spellbook uses generative AI integrated with Microsoft Word to help legal teams draft, review, and manage contracts. It analyzes text in Word, suggests changes for missing clauses and inconsistencies, and checks regulatory compliance; Spellbook Associate can autonomously plan and execute complex legal tasks. It differentiates itself with in-workflow AI inside Word, a privacy-focused large-scale platform, and agentic AI capabilities. Its goal is to boost legal efficiency and accuracy so lawyers spend more time on strategic advice and client service.

Company Size

51-200

Company Stage

Debt Financing

Total Funding

$122.4M

Headquarters

Toronto, Canada

Founded

2018

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Simplify's Take

What believers are saying

  • Spellbook tripled revenue in 2025, targeting $100M ARR by 2026.
  • Spellbook partners with Canadian Bar Association for 40,000 professionals.
  • Spellbook secures $40M RBC debt for acquiring legal AI competitors.

What critics are saying

  • Harvey AI captures Spellbook's enterprise clients with broader platform.
  • Microsoft Copilot obsoletes Spellbook's Word plugin, driving 70% churn.
  • OpenAI's GPT-5 legal tool commoditizes Spellbook's LLM core.

What makes Spellbook unique

  • Spellbook integrates AI directly into Microsoft Word for seamless contract drafting.
  • Spellbook Associate executes complex legal tasks autonomously using GPT-5.
  • Spellbook maintains zero data retention and GDPR/CCPA compliance.

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Benefits

Health Insurance

Wellness Program

Mental Health Support

Stock Options

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Family Planning Benefits

Fertility Treatment Support

Unlimited Paid Time Off

Flexible Work Hours

Remote Work Options

Paid Vacation

Annual wellness allowance

Stock option grants

Growth & Insights and Company News

Headcount

6 month growth

-4%

1 year growth

-1%

2 year growth

4%
Business Wire
Mar 5th, 2026
Spellbook Secures $40M USD Debt Financing from RBCx to Support Strategic Acquisitions in Consolidating Legal AI Market

Spellbook, the AI copilot for contracts used by nearly 4,000 law firms and legal teams globally, today announced it has secured $40 million USD in debt finan...

Stockwatch
Mar 4th, 2026
RBC provides $40M debt financing to AI legal tech startup Spellbook for acquisitions

Spellbook, a St. John's-based legal AI software startup, has secured $40 million in debt financing from Royal Bank of Canada to acquire struggling competitors in the generative AI market. The company, officially named Dialog Enterprises Inc., launched one of the first generative AI tools for lawyers in 2022. Spellbook's AI copilot, powered by large language models including OpenAI's GPT-5, helps lawyers and corporations draft, edit and review legal contracts within Microsoft Word. The company tripled its revenue in 2025 and expects to reach $100 million in annual recurring revenues by year-end, according to CEO Scott Stevenson. The firm serves over 4,000 customers across 80 countries, including Nestlé, Dropbox and eBay. It recently signed a two-year partnership with the Canadian Bar Association to provide AI tools to 40,000 legal professionals.

Spellbook
Oct 13th, 2025
Spellbook Raises $50m Series B led by Khosla Ventures - Spellbook

Today we’re announcing our Series B financing led by Keith Rabois at Khosla Ventures, including participation from Threshold Ventures, Inovia, Bling Capital and Moxxie Ventures.

Law360
Oct 9th, 2025
Spellbook Secures $50M in Series B

Spellbook, a contract software company, announced the closing of a $50 million Series B funding round, valuing the company at $350 million. This brings its total funding to over $80 million.

Business Wire
Jun 5th, 2025
Spellbook Secures $10.9M in Funding to Bring Assistive AI to Lawyers

Spellbook, the AI copilot for lawyers, today announced $10.9M in funding led by Moxxie Ventures, with participation from Thomson Reuters Ventures, Inovia Cap...