Lead AI Automation Engineer, Portfolio Operations
About the role
Company: Define Capital Location: Toronto, Ontario Job Type: Full-time Work Arrangement: Hybrid, with regular onsite visits to portfolio companies in the Greater Toronto Area and surrounding regions
About Define Capital Define Capital is a private investment firm focused on acquiring and building enduring software and technology-enabled businesses. We take a long-term ownership approach and work closely with our portfolio companies to improve operations, strengthen teams, and build scalable systems.
As our portfolio grows, we are looking for a hands-on technical operator who can help our companies use AI and automation to reduce manual work, eliminate bottlenecks, and build more efficient workflows.
About the Role We are hiring a Lead AI Automation Engineer, Portfolio Operations to identify, build, deploy, and maintain AI-enabled workflow automation systems across our portfolio companies.
This is not a strategy-only role. We are looking for someone who can go deep into a business process, spend time with frontline teams, understand how work actually gets done, and then build secure, production-grade systems that automate manual tasks.
The right person will be equally comfortable sitting beside an operations employee to learn a workflow, designing a better process, writing code, integrating systems, and deploying a solution that people use every day.
You will report directly to Define Capital and work closely with leaders and teams at our portfolio companies.
What You’ll Do Work directly with portfolio company leaders and frontline employees to understand manual, repetitive, and document-heavy workflows Map current-state processes, identify bottlenecks, and design improved future-state workflows Build secure, production-grade AI and automation systems that reduce reliance on manual labour Develop solutions involving document intake, OCR, structured data extraction, data validation, workflow automation, database integration, and human-in-the-loop review Use AI, LLMs, APIs, software engineering, and automation tools where appropriate — while avoiding over-engineered or fragile solutions Integrate automation systems into existing business software and operational workflows Design quality-control processes, confidence thresholds, exception handling, audit trails, and review queues Maintain and improve automation systems after launch Measure the impact of each project, including hours saved, headcount reduced or avoided, throughput improvement, error reduction, and bottlenecks eliminated Move from project to project across portfolio companies, becoming deeply embedded in each business long enough to understand the workflow and implement a practical solution Help build Define Capital’s repeatable playbook for applying AI and automation across future acquisitions
Example Projects Projects may include: Automating document-heavy file intake and data entry workflows Extracting structured information from forms, PDFs, emails, spreadsheets, and scanned documents Supporting automation of title-search-related workflows that involve data retrieval, system interaction, and judgment-based review Automating credential verification and contractor-driven data entry processes Building human-in-the-loop systems where AI handles the repetitive work and employees review exceptions or high-risk outputs Replacing manual handoffs with structured workflows, dashboards, and automated processing queues
What We’re Looking For We are looking for a senior, independent builder who can own projects from discovery through implementation.
You should have: Strong software engineering skills, especially in Python Experience building and deploying production-grade systems Practical experience with AI, LLMs, OCR, document extraction, automation, and APIs Strong understanding of databases, data pipelines, application integrations, and workflow systems A cybersecurity mindset, including data privacy, access controls, secure system design, audit logging, and vendor/API risk Ability to work with messy real-world documents, inconsistent inputs, and operational edge cases Strong business process analysis skills Comfort working directly with non-technical employees and business leaders Ability to translate an operational problem into a technical solution Strong judgment on when to automate fully, when to use human review, and when AI is not the right tool Ability to work independently without requiring constant direction Strong communication and change-management skills Willingness to travel to portfolio company sites in and around Toronto as needed
Nice to Have Experience automating document-heavy workflows Experience with OCR, computer vision, LLM-based extraction, RPA, or workflow orchestration tools Experience in private equity portfolio operations, professional services, municipal services, healthcare, credentialing, legal operations, finance, or other process-heavy environments Experience deploying systems in cloud environments Familiarity with SOC 2, privacy, compliance, or secure software development practices Experience working in small or mid-sized businesses where systems and processes may be less formalized
Who This Role Is Not For This role is likely not the right fit if you are mainly interested in AI strategy, research, workshops, or advisory work. We need someone who wants to build real systems, work closely with operators, and take responsibility for turning manual workflows into scalable, secure, automated processes.
What Success Looks Like Success in this role means building automation systems that are actually used by our portfolio companies and that materially reduce manual work.
You will be measured by practical outcomes, including: Reduced manual data entry Faster processing times Fewer operational bottlenecks Improved accuracy and consistency Secure and reliable systems that can be maintained over time Repeatable automation practices that can be applied across future portfolio companies
Ideal Candidate Profile The ideal candidate is a senior technical operator: someone who can write code, understand production systems, work with business users, and redesign workflows.
You are curious enough to sit with employees and learn the details of their day-to-day work, but technical enough to build the system that changes how the work gets done.
You are practical, independent, security-conscious, and focused on measurable business impact.
Compensation Compensation will be competitive and based on experience.
How to Apply Please apply with your resume that includes a workflow, automation, AI system, or internal tool you have built that improved a real business process.
About Define Capital
Define Capital is looking to acquire B2B software and SaaS companies that operate in a niche market. Our sweet spot is profitable companies with $400K to $5M in EBITDA.
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Lead AI Automation Engineer, Portfolio Operations
About the role
Company: Define Capital Location: Toronto, Ontario Job Type: Full-time Work Arrangement: Hybrid, with regular onsite visits to portfolio companies in the Greater Toronto Area and surrounding regions
About Define Capital Define Capital is a private investment firm focused on acquiring and building enduring software and technology-enabled businesses. We take a long-term ownership approach and work closely with our portfolio companies to improve operations, strengthen teams, and build scalable systems.
As our portfolio grows, we are looking for a hands-on technical operator who can help our companies use AI and automation to reduce manual work, eliminate bottlenecks, and build more efficient workflows.
About the Role We are hiring a Lead AI Automation Engineer, Portfolio Operations to identify, build, deploy, and maintain AI-enabled workflow automation systems across our portfolio companies.
This is not a strategy-only role. We are looking for someone who can go deep into a business process, spend time with frontline teams, understand how work actually gets done, and then build secure, production-grade systems that automate manual tasks.
The right person will be equally comfortable sitting beside an operations employee to learn a workflow, designing a better process, writing code, integrating systems, and deploying a solution that people use every day.
You will report directly to Define Capital and work closely with leaders and teams at our portfolio companies.
What You’ll Do Work directly with portfolio company leaders and frontline employees to understand manual, repetitive, and document-heavy workflows Map current-state processes, identify bottlenecks, and design improved future-state workflows Build secure, production-grade AI and automation systems that reduce reliance on manual labour Develop solutions involving document intake, OCR, structured data extraction, data validation, workflow automation, database integration, and human-in-the-loop review Use AI, LLMs, APIs, software engineering, and automation tools where appropriate — while avoiding over-engineered or fragile solutions Integrate automation systems into existing business software and operational workflows Design quality-control processes, confidence thresholds, exception handling, audit trails, and review queues Maintain and improve automation systems after launch Measure the impact of each project, including hours saved, headcount reduced or avoided, throughput improvement, error reduction, and bottlenecks eliminated Move from project to project across portfolio companies, becoming deeply embedded in each business long enough to understand the workflow and implement a practical solution Help build Define Capital’s repeatable playbook for applying AI and automation across future acquisitions
Example Projects Projects may include: Automating document-heavy file intake and data entry workflows Extracting structured information from forms, PDFs, emails, spreadsheets, and scanned documents Supporting automation of title-search-related workflows that involve data retrieval, system interaction, and judgment-based review Automating credential verification and contractor-driven data entry processes Building human-in-the-loop systems where AI handles the repetitive work and employees review exceptions or high-risk outputs Replacing manual handoffs with structured workflows, dashboards, and automated processing queues
What We’re Looking For We are looking for a senior, independent builder who can own projects from discovery through implementation.
You should have: Strong software engineering skills, especially in Python Experience building and deploying production-grade systems Practical experience with AI, LLMs, OCR, document extraction, automation, and APIs Strong understanding of databases, data pipelines, application integrations, and workflow systems A cybersecurity mindset, including data privacy, access controls, secure system design, audit logging, and vendor/API risk Ability to work with messy real-world documents, inconsistent inputs, and operational edge cases Strong business process analysis skills Comfort working directly with non-technical employees and business leaders Ability to translate an operational problem into a technical solution Strong judgment on when to automate fully, when to use human review, and when AI is not the right tool Ability to work independently without requiring constant direction Strong communication and change-management skills Willingness to travel to portfolio company sites in and around Toronto as needed
Nice to Have Experience automating document-heavy workflows Experience with OCR, computer vision, LLM-based extraction, RPA, or workflow orchestration tools Experience in private equity portfolio operations, professional services, municipal services, healthcare, credentialing, legal operations, finance, or other process-heavy environments Experience deploying systems in cloud environments Familiarity with SOC 2, privacy, compliance, or secure software development practices Experience working in small or mid-sized businesses where systems and processes may be less formalized
Who This Role Is Not For This role is likely not the right fit if you are mainly interested in AI strategy, research, workshops, or advisory work. We need someone who wants to build real systems, work closely with operators, and take responsibility for turning manual workflows into scalable, secure, automated processes.
What Success Looks Like Success in this role means building automation systems that are actually used by our portfolio companies and that materially reduce manual work.
You will be measured by practical outcomes, including: Reduced manual data entry Faster processing times Fewer operational bottlenecks Improved accuracy and consistency Secure and reliable systems that can be maintained over time Repeatable automation practices that can be applied across future portfolio companies
Ideal Candidate Profile The ideal candidate is a senior technical operator: someone who can write code, understand production systems, work with business users, and redesign workflows.
You are curious enough to sit with employees and learn the details of their day-to-day work, but technical enough to build the system that changes how the work gets done.
You are practical, independent, security-conscious, and focused on measurable business impact.
Compensation Compensation will be competitive and based on experience.
How to Apply Please apply with your resume that includes a workflow, automation, AI system, or internal tool you have built that improved a real business process.
About Define Capital
Define Capital is looking to acquire B2B software and SaaS companies that operate in a niche market. Our sweet spot is profitable companies with $400K to $5M in EBITDA.