Jobs in Milton, Canada

Description

Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle.

The Role

You will report to the CTO and be responsible for driving engineering execution at scale, including delivery, quality, and talent growth. You will manage a team of Engineering Directors and play a critical leadership role in shaping the engineering culture, building high-performing teams, and ensuring predictable, high-quality delivery across our platform.

You will oversee the design, development, and scaling of complex distributed systems, including our Accounts Payable, Payment Processing, Expense Management and AI platforms. You will partner closely with cross-functional leaders in Product, Design, and Operations to deliver reliable, secure, and high-performance services to our customers.

Responsibilities

• Provide executive leadership for engineering execution — ensure high-quality delivery, predictable velocity, and efficient processes across all product areas.
• Build, scale, and lead a global engineering organization of 100+ engineers, cultivating a strong culture of innovation, collaboration, and accountability.
• Drive long-term technical strategy and roadmaps, ensuring the organization is well-positioned to handle rapid growth, new product lines, and high transaction volumes.
• Establish engineering standards and practices across backend, frontend, security and infrastructure, including testing, observability, and code quality.
• Own technical direction and architectural oversight for critical platforms, ensuring robust, scalable, and secure systems that power all our products
• Guide design and technology choices at a systems level, fostering best practices in reliability, performance, security, and compliance.
• Partner with Product, Design, and Operations to align engineering priorities with business objectives and deliver impactful customer experiences.
• Develop and mentor engineering leaders to scale management capacity and empower teams.
• Champion AI and automation to enhance developer efficiency, improve velocity, and support the company’s innovation goals.

• 10+ years of professional experience working on building products using modern software engineering processes, with a proven track record of building and scaling high-volume B2B or B2C product
• Experience in scaling engineering teams to 100+ engineers and working in a global engineering organization.
• Technically strong with experience building large-scale enterprise-grade systems, preferably in Python and AWS.
• Demonstrated ability to both perform hands-on engineering and lead a team of software engineers and product managers.
• Deep expertise in building complex software systems, with skills in both backend and frontend. Expertise in Postgres, Python and Django is a big bonus.
• You think critically about your work and ask questions in order to improve the product, not only on its technical implementation but also on how well it's serving the users' needs.
• You have strong communication skills and are able to explain complex technical topics and engage with multiple stakeholders across the company, and with customers.
• Experience working in an early-stage startup is a huge plus

• Compensation: $250,000 per year (base)
• Opportunity to drive a business that is processing $30B+ volume in payables annually, and growing.
• Opportunity to shape engineering culture and technical solutions for a fast-growing SaaS company.
• Competitive compensation, including base salary, equity and performance incentives.
• Collaborative, remote-first culture with a focus on innovation and impact.
• Comprehensive benefits package, including healthcare, 401(k), and flexible PTO

Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply.