Senior Software Developer Jobs in Toronto, ON (NOW HIRING)

Clio is the global leader in legal AI technology, empowering legal professionals and law firms of every size to work smarter, faster, and more securely.

We are transforming the legal experience for all by bettering the lives of legal professionals while increasing access to justice.

We are currently seeking a Senior Software Engineer, AI to join our Knowledge Extraction Team.

The Senior Software Engineer, AI is a hands-on technical leader responsible for building, operating, and evolving the systems that turn large volumes of semi-structured legal documents into structured, trustworthy legal data. Reporting to the Development Manager, this role focuses on delivering reliable, secure, and scalable AI-enabled pipelines and services that process caselaw across many jurisdictions, at a scale of millions of documents and tens of millions of citation relationships.

You will work closely with partners across editorial and legal data teams, Data Engineering, and Platform Engineering to turn real problems in legal information into production-grade solutions. This role owns the full lifecycle of what you build, from design and implementation through monitoring, iteration, and long-term support.

What you'll work on:

- Design, build, and operate backend services and data pipelines that extract, classify, and resolve information from semi-structured legal documents at scale.

- Build and operate LLM-powered workflows (batch classification, prompt design and calibration, retrieval, and model integration) using providers such as OpenAI and AWS Bedrock.

- Improve the accuracy and coverage of core capabilities like citation recognition, citation resolution, and treatment detection, including work across multiple jurisdictions.

- Work with large, heterogeneous document sets and curated evaluation sets to measure model quality and drive it up over time.

- Ensure solutions are observable, reliable, secure, and cost-efficient, with clear monitoring and operational ownership (e.g. Datadog).

- Operate in the cloud (AWS: Batch, Lambda, ECS, RDS/Postgres, S3, and search/vector stores such as Vespa) with solid CI/CD practices.

- Contribute to and uphold responsible AI standards, including privacy, security, legal accuracy, and audibility, given the sensitivity of legal data.

- Collaborate with cross-functional and non-technical partners (including legal editors) to translate ambiguous problems into clear technical designs and shipped solutions.

- Act as a technical mentor and thought partner within the team, helping raise the bar for engineering quality and delivery.

What you may have:

- 4+ years of experience in software engineering, backend, data engineering, or AI systems development.

- Hands-on experience delivering production-grade systems that integrate data, APIs, and complex workflows.

- Strong proficiency in Python. Experience with Ruby is an asset (some of our services are Ruby-based).

- Experience working with semi-structured or heterogeneous data (documents, JSON, nested or variant records): parsing, extraction, classification, and entity resolution.

- Experience with AI/ML or LLM-powered systems (e.g. prompt design, orchestration, retrieval, model integration, or evaluation).

- Working knowledge of cloud platforms (AWS preferred), SQL, and processing data at scale.

- Solid understanding of system design, reliability, observability, and operational best practices.

- Ability to work effectively with non-technical and domain stakeholders and translate business needs into technical solutions.

- Experience operating in environments with security, privacy, or compliance constraints.

- Bachelor's degree in Computer Science, Engineering, Data, or equivalent practical experience.

- A keen interest in improving your craft, including using AI.

What you will find here:

Compensation is one of the main components of Clio's Total Rewards Program. We have developed a series of programs and processes to ensure we are creating fair and competitive pay practices that form the foundation of our human and high-performing culture.

Some highlights of our Total Rewards program include:

• Competitive, equitable salary with top-tier health benefits, dental, and vision insurance

• Hybrid work environment, with expectation for local Clions (Vancouver, Calgary, Toronto, Dublin, London, New York City and Sydney) to be in office min. twice per week.

• Flexible time off policy, with an encouraged 20 days off per year.

• $2000 annual counseling benefit

• RRSP matching and RESP contribution

• Clioversary recognition program with special acknowledgement at 3, 5, 7, and 10 years

Diversity, Inclusion, Belonging and Equity (DIBE) & Accessibility

Our team shows up as their authentic selves, and are united by our mission. We are dedicated todiversity, equity and inclusion. We pride ourselves in building and fostering an environment where our teams feel included, valued, and enabled to do the best work of their careers, wherever they choose to log in from. We believe that different perspectives, skills, backgrounds, and experiences result in higher-performing teams and better innovation. We are committed to equal employment and we encourage candidates from all backgrounds to apply.

Clio provides accessibility accommodations during the recruitment process. Should you require any accommodation, please let us know and we will work with you to meet your needs.

Learn more about our culture atclio.com/careers

We're a Human and High Performing AI company, meaning we use artificial intelligence to improve all of our operations. In recruitment, AI helps us streamline the process for greater efficiency. However, we've built our systems to ensure that a human always reviews AI-generated output, and we never make automated hiring decisions.

Disclaimer: We only communicate with candidates through official @clio.com email addresses.