LightSpeed Retail

Legal Operations & Automations Manager

LightSpeed Retail$90K — $105K *
Legal & Accounting
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2-5 years experience in legal operations, systems engineering, or automation development
  • Proven ability to design and configure workflow automations
  • Familiarity with AI tools and technology solution evaluation
  • Strong cross-functional communication skills
  • Analytical thinking and adept problem-solving abilities
  • Experience in managing conflicting priorities in fast-paced settings
  • Fluency in English required due to global operations

Responsibilities

  • Conduct observations and map processes of legal team activities for automation opportunities
  • Prioritize automation initiatives based on business value and stakeholder impact
  • Design and test end-to-end automated workflows for legal processes
  • Build custom intake forms and automate document generation
  • Create reusable templates for standardizing processes
  • Document processes for maintainability and team understanding
  • Establish and monitor automation performance metrics to demonstrate ROI

Benefits

  • Flexible paid time off and remote work policies
  • Equity options to share in company success
  • Contributions to a pension plan for future security
  • Training opportunities for skill and career growth
  • Health and wellness credits for employee well-being
  • Time off for volunteering in the community
  • Employee-led interest groups and social committees
  • Computer purchase program for personal gear
  • Enhanced parental leave to support family growth
Full Job Description
We are looking for a Legal Operations & Automations Manager to act as the primary architect of our legal tech stack, internal processes, and AI/automation initiatives. In this role, you will partner daily with legal counsel, IT, Sales, and RevOps to transform manual, time-consuming tasks into streamlined, automated workflows.

Whether your background is in Legal Operations / Paralegal management with a passion for building workflows, or in General Operational Automations / Systems Engineering with an interest in applying low-code/AI solutions to legal operations, we want to hear from you!

What you'll be doing:

  • Conduct detailed observations and process-mapping of daily legal team activities to identify automation and efficiency opportunities.
  • Prioritize automation initiatives based on business value, risk reduction, time saved, and stakeholder impact.
  • Design and test end-to-end automated workflows for various legal workflows and review processes leveraging existing tools like Spellbook, IronClad and Glean.
  • Build custom intake forms, conditionally routed approvals, and automated document generation templates.
  • Create reusable templates and automation libraries to standardize processes and accelerate future projects.
  • Document processes clearly so that automations are maintainable and team members can understand and build on your work.
  • Develop prompt best practices and practical playbooks to help legal team members leverage AI effectively without needing technical expertise.
  • Partner with lawyers, paralegals, and business stakeholders to gather requirements, validate solutions, and ensure adoption.
  • Establish and monitor automation performance by tracking KPIs (e.g., cycle times, cost/time savings, error rates, adoption rates) to measure ROI and present insights to leadership.
  • Drive a culture of process-driven thinking across the legal team and champion best practices in documentation and governance.

What you need to bring:
  • 2-5 years combined experience in legal operations, systems engineering, process improvement, systems implementation, or automation development
  • Proven track record of designing, building, and configuring (not just using) workflow automations and integrations
  • Familiarity with modern AI tools, prompt engineering, and an eagerness to evaluate "build vs. buy" technology solutions
  • Excellent cross-functional communication and ability to translate technical capabilities to non-technical legal/business stakeholders
  • Strong analytical thinking and problem-solving skills
  • Ability to prioritise and manage competing demands in a fast-paced environment
  • Experience with coaching, teaching, and enabling colleagues and stakeholders
  • As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

Even better if you have, but not necessary:
  • Prior experience at a high-growth SaaS or technology company.
  • Hands-on experience with legal tech tools such as Ironclad, Spellbook, Glean, CoCounsel, or Harvey.
  • Background in data analytics, reporting dashboards, and/or CRM/ERP integrations (e.g., Salesforce).

We know that people are more than what's on their CV. If you're unsure that you have the right profile for the role... hit the 'Apply' button and give it a try!

You'll enjoy:
  • A flexible work environment that empowers you to do your best work
  • A culture that celebrates performance
  • The chance to make an impact in a team that's big enough for career growth, but lean enough to make your voice heard
  • Career-defining opportunities

Plus benefits designed to keep you happy, healthy and fulfilled.
  • Flexible paid time off and remote work policies
  • Equity options, because this is your company too
  • Contributions to your pension plan. Your future matters
  • Training opportunities to grow your skills and career
  • Health and wellness credit so you feel your best
  • Time off to volunteer and give back to your community
  • Interest groups, employee led networks, social committees to sponsored sports teams
  • Computer purchase program to get your personal Macbook
  • Enhanced parental leave to support growing families

Fuel your growth. Find your people.

At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you-all within a driven, diverse and inclusive team that's passionate about empowering our communities

At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skill set, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the total compensation for this position to be in the range of $90,000 TO $105,000 CAD. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, RRSP plan and match, paid parental leave top-up, and paid time off.

Please note that this compensation information is solely for candidates hired to perform work within Ontario (update to BC if posted in Vancouver) and reflects the amount Lightspeed is willing to pay at the time of this posting. This role represents an existing vacancy at Lightspeed. Lightspeed uses artificial intelligence-enabled tools to support certain aspects of the recruitment process; all hiring decisions are made by our recruiting and hiring teams.

About LightSpeed Retail

LightSpeed Retail is a cloud-based point-of-sale and e-commerce software provider for retailers and restaurateurs. The company was founded in 2005 by Dax Dasilva and is headquartered in Montreal, Canada. LightSpeed Retail's platform allows businesses to manage their inventory, process transactions, and analyze sales data. The company's mission is to help businesses grow by providing them with the tools they need to succeed. LightSpeed Retail has raised over $290 million in funding from investors such as Caisse de dépôt et placement du Québec, iNovia Capital, and Accel Partners.
Learn more about LightSpeed Retail
Size
1,000 employees
Market Cap
$18.4 billion
Industry
Founded
2005
5 Year Trend
+48.5%

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