Staff Software Engineer (AI)

Location: Pay varies by work location; Canada locations are categorized into Zone A and Zone B.

Salary: CAD 222,900–334,300 annually.

Company

hirify.global builds technology and financial services products through brands including Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto.

What you will do

• Own the technical strategy, architecture, and long-term evolution of the go-to-market technology stack.
• Design, build, and operate production-grade AI agents and automated workflows that improve sales productivity and decision-making.
• Lead technical execution by setting direction, decomposing complex problems, reviewing designs, and mentoring engineers.
• Work hands-on across prototyping, implementation, testing, deployment, and production operations.
• Partner with Sales, Sales Strategy & Operations, Product, Data, and Engineering leaders to turn business problems into scalable solutions.
• Establish evaluation methods, observability, security controls, reliability practices, and guardrails for AI systems using sensitive business data.

Requirements

• 12+ years of related experience with a Bachelor’s degree, 8+ years with a Master’s degree, 5+ years with a PhD, or equivalent experience.
• Experience setting technical direction and delivering complex, business-critical systems across multiple teams or functional areas.
• Experience building and operating production software using large language models, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
• Experience taking AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
• Strong software engineering and system-design skills across application, service, integration, and data layers.
• Ability to lead through technical influence, mentorship, architecture, and direct contribution without formal reporting authority.

Nice to have

• Familiarity with sales processes or go-to-market systems such as lead management, opportunity management, forecasting, account planning, or CRM platforms.

Culture & Benefits

• Inclusive workplace and equal opportunity employment practices.
• Reasonable accommodations are available throughout the recruitment process.
• Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning benefits are offered.
• Automated AI tools may be used to evaluate applications in accordance with local regulations and privacy requirements.

Hiring process

• Candidates may submit up to 9 active applications within a 60-day period.
• Reapplications to the same role are accepted 90 days after a previous application has been reviewed.