AI Automation Engineer

AI Automation Engineer

Aspire Software is seeking an AI Automation Engineer to join our growing team in Toronto!

About The Role

Aspire Software is looking for an AI Automation Engineer, someone who can design, build, and ship AI agents that either transform how our portfolio companies operate or become standalone products our customers pay for. This is not a research role. You will be embedded directly inside Aspire Software, working alongside portfolio company teams, understanding their operations, and building AI agents that handle real work: customer service, sales outreach, onboarding, documentation, and more. Some of what you build will replace manual workflows within Aspire’s portfolio companies. Some of it will become new revenue-generating products sold to their customer bases. Either way, it ships to real users.

Aspire Software is an operating group of Valsoft Corporation, a long-term investor in vertical market software businesses. Valsoft acquires and operates software companies with a permanent ownership mindset, emphasizing autonomy, disciplined growth, and long-term value creation. Aspire partners with and operates vertical market software businesses globally, enabling them to scale sustainably while maintaining entrepreneurial independence.

The successful candidate will be based anywhere within commutable distance of our office in Toronto, working in a hybrid work model!

What Your Day Will Look Like

• Build Internal AI Agent Teams: Design and deploy AI agents that handle operational work across Aspire Software and its portfolio companies, including customer support tiers 1 and 2, SDR and sales outreach, onboarding automation, content and marketing workflows, and engineering maintenance.
• Measure impact in hours of labor replaced or team output increased.
• Work directly with portfolio company operators to identify the highest value automation opportunities.
• Build External AI Products: Develop new AI-powered products such as vertical voice agents, AI copilots, workflow automation tools, and AI documentation systems tailored to Aspire’s vertical markets.
• Own the product from prototype through launch, including reaching first paying customers.
• Ship and Iterate: Move fast from idea to MVP to production.
• Run beta tests with real users, gather feedback, and improve continuously.
• Collaborate cross-functionally with product, engineering, and go-to-market teams.

About You

What You Bring

• Proven track record of building products, tools, projects, startups, or side projects that went live.
• Strong working knowledge of AI and machine learning tools, large language models, and agent frameworks.
• Ability to go from zero to functional prototype quickly.
• Comfort with ambiguity. You will often be defining the problem as much as the solution.
• Bias toward action over planning.

Nice to Have

• Experience building AI agents, voice agents, or workflow automation.
• Background in vertical SaaS or B2B product development.
• Familiarity with the security industry.
• Previous startup or founder experience.
• Experience working across multiple product lines or business units.
• A bachelor's degree in Artificial Intelligence, Software Engineering, Computer Science, Robotics, Mechanical Engineering or a similar discipline.

Why Join Aspire Software

• You build things that ship to real customers, not internal tools that collect dust.
• High ownership. You define what gets built and how.
• Growth path tied to the impact you create, whether that is scaling an internal AI operation or launching a product that becomes its own business unit.

Compensation

Base Salary: Competitive

Variable Compensation: High-upside, performance-driven pay tied directly to the value you create — structured as a percentage of internal cost savings from AI agent deployments and incremental revenue from new AI products. The more impact you drive, the more you earn.

Benefits: Health coverage and a dedicated building budget for APIs, tools, and infrastructure.

Ready to Build With Us?

If you're energetic, scrappy, and ready to build something exceptional from the ground up, we would love to hear from you.

Required

• Your resume
• A short note (5–10 sentences) describing the first AI agent you would build if you started tomorrow, and why.

For information about Aspire Software, please visit our website at www.aspiresoftware.com

We thank all applicants for their interest; however, only those candidates selected for an interview will be contacted.

Key skills/competency

The AI Automation Engineer role at Aspire Software requires a blend of technical expertise and a product-oriented mindset. Key skills include designing, building, and shipping AI agents and products, proficiency with AI/ML tools and LLMs, rapid prototyping, problem-solving in ambiguous environments, and a strong bias for action. Successful candidates will demonstrate experience with operational automation, customer-facing AI products, and cross-functional collaboration. The role emphasizes delivering tangible impact through AI solutions, whether improving internal operations or creating new revenue streams.