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Director, Engagement - Canada

legora

OnSite Toronto
Social Media IT Governance Advertising

Job Score

100 pts
On-site model (+70) Social Media (+10) IT Governance (+10) Advertising (+10)

About Us

Legora is redefining how legal work gets done. Not built for lawyers, built with them. We work alongside the world’s best legal teams, who expect excellence, precision, and speed, and we hold ourselves to the same bar.

Our AI-native workspace lets legal professionals move faster, think more clearly, and operate with sharper precision. By analysing thousands of documents in minutes and powering end-to-end workflows, we cut through complexity, teams can focus on what matters: judgment, strategy, and outcomes.

1,000+ customers across 50+ countries trust us, including Cleary Gottlieb, Goodwin, Linklaters, White & Case, Dentons, and Barclays. We’ve scaled to $100M+ in ARR, with teams across Europe, North America and APAC, and continue to expand through acquisitions including Qura, Walter AI and Graceview.

We partner with world-class performers: including Aaron Judge and the New York Yankees, Ludvig Åberg (and his caddie), and campaigns featuring Jude Law.

Joining Legora means three things.

  • We lean in: ownership over titles, outcomes over intentions.

  • We fight for excellence: high standards, direct, ego-free feedback.

  • We grow together: as a team and with our customers.

Mission before ego. Everyone contributes. No one coasts.

If you’re driven by impact, pace, and raising the bar. This is the place.

About the Role

The way legal work gets done is changing, and Engagement is at the center of that transformation. We're looking for an experienced, strategic Engagement Director to build and lead a multi-layered team within our growing Engagement org that helps the world's top law firms and corporations fundamentally change the way they work with Legora.

This is a role for someone who has led change inside large, complex organizations and built and scaled the teams — and the leaders — that deliver it, and knows that real transformation is designed and managed. You will own the adoption and long-term success of an entire vertical (e.g., Enterprise Firms, East or Mid-Market Corps, West) — leading a team of Engagement Associates, Managers, and Senior Managers who build the relationships and define the outcomes, while you reserve yourself for the most strategic accounts and C-suite relationships as the senior strategic advisor who ensures Legora becomes an embedded part of how legal teams operate.

At the heart of the role is defining the engagement model for your vertical and building the frameworks and standards your team uses to design each client's adoption playbook and deliver multi-year change-management programs that transform how they work. Across the portfolios in your vertical you'll set the bar for how a tailored roadmap is built, how initiatives are sequenced from initial rollout through firm-wide scaled adoption, how measurable outcomes and ROI are defined, and how the program evolves as new AI capabilities and use cases emerge.

You will be critical as we continue to build a best-in-class adoption program at Legora, partnering with Leadership to scale the teams, leaders, and standards that help clients realize measurable ROI, expand successful use cases and transform the way their teams work.

What You’ll Do

You'll lead the post-sale customer experience for a vertical (e.g., Enterprise Firms, East or Enterprise Corporates, East) — owning onboarding, adoption and long-term value realization across every account in it, through the teams and leaders you build. Specifically, you will:

  • Define the engagement model for your vertical, setting the standard for how your team designs each client's adoption playbook: the tailored change-management approach, stakeholder map and target outcomes for how that customer adopts Legora and transforms the way they work.

  • Build the operating rhythms — portfolio and pipeline reviews, health inspection, coaching cadences — that keep the team executing against those playbooks at scale, sequencing initiatives from initial rollout to firm-wide scaled adoption and adapting as clients' needs and Legora's capabilities evolve.

  • Coach the team — including other people managers — to act as strategic advisors who deeply understand client goals and legal workflows, reserving yourself for the most strategic accounts and C-suite relationships, to engage executive sponsors, surface high-impact opportunities, and guide clients toward maximum value from Legora.

  • Set the standard for how the team drives sustained value through a structured operating cadence: success plans, enablement, stakeholder check-ins, training and value reviews — turning what works across portfolios into repeatable, scalable motions the whole vertical adopts.

  • Partner with Leadership and orchestrate engagement from cross-functional teams across your vertical to accelerate client success (GTM, Product, Legal Engineering, Engineering, Marketing, Support), maintaining end-to-end context across your portfolio and shaping how Legora delivers value.

  • Partner with GTM leadership on key commercial moments across the vertical to ensure seamless handoffs, continuity, and a great customer experience, and to identify and realize expansion opportunities — coaching the team to lead these conversations and stepping in on the most complex or strategic renewals and expansions.

  • Translate vertical-level feedback into action by collaborating closely with Leadership, Product, Engineering, and Marketing to shape roadmap, positioning, and enablement.

What You Bring

You care deeply about customer outcomes and you know that transformation has to be designed and led — and that scaling it across a vertical takes a high-performing team and the leaders to run it. You're proactive, strategic and comfortable steering demanding, senior stakeholders and executive sponsors through significant change. You take pride in being the reason customers — and the teams behind them — adopt, grow and succeed.

We're looking for:

  • A consulting or transformation background, with a demonstrated track record of designing and delivering change-management programs inside large, complex organizations — and building and leading the teams — and leaders — that deliver them at scale.

  • Experience building the standards and operating rhythms that scale tailored, client-level transformation roadmaps and adoption plans across a vertical and steering them to measurable outcomes.

  • 10+ years in management consulting, customer success, account management, or a related field, with 5+ years managing client-facing teams — including other managers and team leads — ideally with exposure to high-growth B2B SaaS or Legal Tech.

  • A track record of owning adoption, retention, and satisfaction across a vertical of enterprise clients and senior stakeholders — and of developing the people and leaders who deliver those outcomes.

  • Experience working with legal, compliance, or other regulated and complex industries or the ability to learn a complex domain exceptionally fast.

  • Strong operational discipline; you build inspection frameworks and run tight rhythms that keep multi-workstream initiatives moving across multiple teams and your clients confident.

  • Excellent communication skills and strong executive presence — written, verbal, and interpersonal. You are trusted in the boardroom with C-suite and legal leaders, coach your team and leaders through them, and roll up your sleeves with hands-on teams.

  • High EQ: you know when to listen, when to advise, when to coach and when to act — and when to step in versus let your team and leaders lead.

  • A love of fast-paced, early-stage environments where you build the playbook, the team and the function, not just build for yourself.

  • Deep data fluency; you read portfolio metrics and account health with rigor and use them to drive decisions across the vertical.

What’s In It For You

  • Global collaboration: Partner with teams and clients domestic and internationally.

  • Competitive package: Comprehensive salary, benefits, and tools for success.

  • Meaningful work: Your efforts shape how thousands of lawyers use AI daily.

  • In-person environment: Toronto office designed for ambitious builders.

Legora is an Equal Opportunity Employer

At Legora, we believe great teams are built on diversity of thought and experience. We’re proud to be an equal opportunity employer and committed to creating an inclusive, high-performance culture where everyone can do their best work. We welcome people of all backgrounds and don’t discriminate based on race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, disability, veteran status, or any other characteristic protected by law.

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About Social Media

The Social Media area is one of the most dynamic and constantly evolving fields in digital marketing. Social media professionals are responsible for creating, managing, and optimizing brand presence on digital platforms, building engagement and community with the target audience.

Key skills include social media management (Instagram, TikTok, LinkedIn, Facebook, YouTube), social media content creation, community management, paid social media (Meta Ads, LinkedIn Ads, TikTok Ads), metrics analysis, and strategic planning. Tools like Hootsuite, Sprout Social, Buffer, Later, and analytics platforms are essential.

Social media professionals in technology companies are highly valued, especially those who master paid social, social media analytics, and content strategies for different platforms. The field offers opportunities from analyst to head of social media, with a focus on growth, engagement, and return on investment.

About IT Governance

IT Governance is the area responsible for ensuring that information technology resources are used strategically, efficiently, and in compliance with standards and regulations. IT governance professionals ensure that technology supports business objectives in a secure and reliable manner.

Key skills include IT service management (ITIL), IT audit and compliance, risk management, business continuity, disaster recovery, metrics and indicators (SLAs, KPIs), and strategic alignment between IT and business. Frameworks like COBIT, ITIL, ISO 27001, and compliance standards are essential.

IT Governance professionals in technology companies are highly valued, especially those who master ITSM, IT audit, and risk management. The field offers opportunities from governance analyst to CIO/CTO, with a focus on efficiency, compliance, security, and business value.

About Advertising

The Advertising area is aimed at the planning, creation, and delivery of communication campaigns to promote brands, products, ideas, or services. Professionals in the sector work in advertising agencies or in-house marketing departments in creative fields (art direction, copywriting), strategic planning, account management, and media buying.

Discover Other Areas

Understand the scope of work, key skills, and tools used in different career areas.

About Artificial Intelligence

Artificial Intelligence is currently the fastest-growing field in the technology market. The revolution in generative models (GPT, Claude, Gemini) has created massive demand for AI-specialized professionals.

Key areas of practice include Machine Learning Engineering, MLOps, Prompt Engineering, AI Research, and Applied AI. Python, TensorFlow, PyTorch, and LLM knowledge are essential skills.

AI salaries are the highest in the technology sector, with many remote work opportunities at international companies.

About Content

The Content and Social Media area is essential for building digital presence and audience engagement. Professionals create content strategies, manage social networks, and develop impactful brand narratives.

Key skills include copywriting, storytelling, community management, metrics analysis, audiovisual production, and knowledge of each platform algorithms.

With the growth of influencer marketing and social commerce, this area continues to generate new career opportunities.

About Engineering

Software Engineering goes beyond traditional development, focusing on scalability, performance, and system architecture. Software engineers are responsible for designing infrastructures that support millions of simultaneous users.

Skills include microservices architecture, DevOps, cloud computing, application security, and performance optimization. Knowledge of containerization (Docker, Kubernetes) and CI/CD is increasingly required.

Senior software engineers are rare and highly compensated professionals, with opportunities at major global tech companies.

About Data

The Data field has undergone a radical transformation with the rise of Generative AI. Data professionals are fundamental for evidence-based decision-making across all industries.

Key specializations include Data Engineering, Data Science, Business Intelligence, Machine Learning Engineering, and Analytics. Tools like SQL, Python, Spark, dbt, and cloud platforms (AWS, GCP, Azure) are essential.

The data market continues with high demand and salaries among the most competitive in the technology sector, with many remote work opportunities.

About Account Manager

The Account Manager is the professional responsible for managing and expanding the relationship with clients after the sale. They act as a strategic partner, ensuring satisfaction, retention, and account growth, connecting client needs with company solutions.

Key skills include relationship management, negotiation, upsell and cross-sell, contract renewal, account planning, business reviews, metrics analysis (NPS, churn, LTV), and CRM knowledge (Salesforce, HubSpot). Communication, empathy, and business vision are fundamental differentiators.

Account Managers in technology and SaaS companies are highly valued, especially those who can increase recurring revenue (MRR/ARR) through account expansion and churn prevention. The field offers opportunities from account executive to director of accounts, with a focus on strategic relationship, revenue growth, and customer success.

Career Guides

Technology Career Guide

Planning, skills, interviews, and professional growth in IT, Data Science, DevOps, and Product.

Read full guide →

Design Career Guide

UX/UI, Graphic Design, Product Design. Portfolio, tools, interviews, and growth in the Design field.

Read full guide →

Marketing Career Guide

SEO, Paid Media, Growth, Content Marketing. Certifications, tools, and strategies to grow in Digital Marketing.

Read full guide →

Finance Career Guide

Financial market, investments, corporate finance, certifications, and strategies to grow in the financial field.

Read full guide →

Communication Career Guide

Journalism, PR, Corporate Communication, Content Marketing, and Multimedia Production.

Read full guide →

Administration Career Guide

Business Management, HR, Logistics, Consulting, Project Management, and Entrepreneurship.

Read full guide →

Data Career Guide

Data Science, Data Engineering, BI, Machine Learning, and AI. From training to the job market.

Read full guide →

Product Career Guide

Product Management, Product Ownership, Agile, Scrum, and OKRs. From strategy to execution.

Read full guide →

Tech & Remote Glossary

Stop getting lost in interviews and job descriptions

The job market, especially within tech and global companies, has developed its own dialect. Not understanding these acronyms can make you lose valuable opportunities or poorly negotiate your contract. To end this problem, we created the Definitive Glossary for the Remote Professional.

🏢 Work Models & Routine

Async (Asynchronous Work)
A communication model where responses don't need to be immediate. Instead of back-to-back meetings, the team relies on well-structured documents, threads, and messages. It's the gold standard for global companies spanning multiple time zones.
Sync (Synchronous Work)
The opposite of Async. It requires the team to be online and available at the same time for meetings, live chats, and real-time collaboration.
Daily / Stand-up
A quick daily meeting (usually 15 minutes) common in Agile (Scrum) methodologies. The team answers three questions: What did I do yesterday? What will I do today? Are there any blockers?
All-Hands / Town Hall
A company-wide meeting involving all employees. Usually led by the founders (C-Levels) to present results, new goals, and answer team questions.
1:1 (One-on-One)
A recurring individual meeting between a professional and their direct manager. It is used for career alignment, feedback, and problem-solving, not just for project status updates.

💰 Contracts, Benefits & Compensation

PTO (Paid Time Off)
Instead of strict, categorized leave policies, modern US companies usually offer a flexible pool of days (e.g., 20 days of PTO, or even "Unlimited PTO") that you can use for vacations, sick days, or personal matters, while receiving your regular compensation.
Equity / Stock Options
Company ownership. The startup offers you the right to buy shares at a heavily discounted strike price in the future. If the company grows, goes public, or is acquired, these shares can be highly lucrative.
Vesting (Vesting Schedule)
The rule that controls your Equity. It usually lasts 4 years. You don't get all the shares on day one; you "earn" them gradually as you stay with the company. A "1-year Cliff" means you must stay for at least one year to receive your first batch of shares.
RSUs (Restricted Stock Units)
Unlike Stock Options (where you have the right to buy the stock), RSUs are actual shares the company grants you as a bonus or part of your compensation package, following a strict Vesting schedule.
Independent Contractor (1099 / B2B)
The most common international hiring model for global talent working for US companies. You act as a service provider (business-to-business), receiving the gross salary (often six-figure compensation) without standard local payroll tax deductions at the source.

🤖 Recruitment & Hiring Process

ATS (Applicant Tracking System)
The "robot" that reads your resume. Software like Greenhouse, Ashby, and Workday are used to filter candidates by keywords before a human even looks at the document. (Pro tip: this is why your resume must be clean, semantic, and have the right keywords).
JD (Job Description)
The document that lists the responsibilities, technical requirements, and benefits of the open position.
Cultural Fit
The interview stage that evaluates if your core values, communication style, and worldview align with the company's culture. This is the ultimate test of your Soft Skills.
Onboarding
The integration process. It's the period of your first few weeks at the company, where you get your access credentials, learn about the culture, study the internal documentation, and understand how the product works.

🚀 How to use this to your advantage?

The secret isn't just knowing what these acronyms mean, but using them actively. If during an interview for a premium tech role you ask, "How does your PTO policy and Vesting schedule work?", the recruiter will immediately perceive you as a high-level professional, familiar with the global market standards.

The remote job market requires preparation. And having the right vocabulary is the first big step to securing six-figure proposals and standing out among thousands of applicants.

Expert Tip

Data-Driven: How Data Defines Company Success or Failure

The Data-Driven Era: How Data Culture Defines Company Success or Failure

Published by Mondywork | Category: Data / Business Intelligence

The End of Corporate Gut Feeling

In the past, major business decisions were made based on intuition, previous experience, or the famous "gut feeling" of directors (what the market refers to as the HiPPO - Highest Paid Person's Opinion). Today, however, in a highly competitive and globalized corporate ecosystem, relying on guesswork is the fastest recipe for bankruptcy.

Digital transformation didn't just connect processes; it generated a massive volume of information. The companies that thrive are those that know how to capture, clean, and transform this raw data into actionable insights.

"Data-driven organizations are 23 times more likely to acquire customers, six times as likely to retain those customers, and 19 times as likely to be profitable as a result."
McKinsey Global Institute Study

What Does it Mean to Have a Data-Driven Culture?

Being Data-Driven doesn't just mean subscribing to expensive Analytics tools or having a beautiful dashboard on the office wall. It's a fundamental shift in organizational culture, where truth is sought in the numbers before any action is executed.

  • Predictability: Predictive models allow companies to forecast market trends, customer churn, and operational bottlenecks before they happen.
  • Risk Mitigation: Decisions based on statistics drastically reduce the margin of error in investments and new product launches.
  • Personalization at Scale: Behavioral analysis enables marketing to deliver exactly what the user wants, right when they have the highest propensity to buy.

The Impact of Business Intelligence (BI) and Big Data

To extract the true value from information, companies are building robust Business Intelligence (BI) and Big Data departments. ETL (Extract, Transform, Load) processes, Data Lakes architecture, and the mastery of software like Power BI and Tableau have become the backbone of top-tier US startups and unicorns.

The Harvard Business Review has repeatedly highlighted that the professional who can translate complex data into business language is a modern corporation's most valuable asset. It's not enough to have the data; you must know how to tell a story with it (Data Storytelling).

The Job Market: The Hunt for Data Talent

With this paradigm shift, the demand for Data Engineers, BI Analysts, Data Scientists, and Analytics Engineers has skyrocketed. International companies—especially in the US and Europe—are aggressively hiring global professionals for 100% US Remote roles, offering highly competitive six-figure compensation packages.

For these companies, which use rigorous Applicant Tracking Systems (ATS like Ashby, Workday, and Greenhouse), the ideal candidate is one who seamlessly blends technical mastery (SQL, Python, DAX) with a sharp business acumen.


References and Recommended Reading

  • McKinsey & Company: The data-driven enterprise of 2025.
  • Harvard Business Review: How to Build a Data-Driven Culture.
  • Gartner: Top Trends in Data and Analytics.

Master the art of turning data into revenue?

The best US startups and global tech companies are actively looking for analytical professionals like you, offering remote roles with premium compensation. Don't miss out on the top Data, BI, and Machine Learning opportunities in the market.