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About the Role

This is the most senior engineering hire Bold AI will make. The person in this role owns the technical spine of the company, including the agent platform, engagement methodology, and engineering patterns. The role requires an engineer who has built enterprise agentic systems, can architect for the future, and is ready to own the function end-to-end.

Responsibilities

• Own end-to-end technical architecture across Bold AI's products and client engagements.
• Define and defend vendor, model, and platform decisions considering cost, scalability, dependency risk, and regulatory exposure.
• Select and implement orchestration layers, agent harnesses, and control plane tooling.
• Evolve infrastructure strategy as client load and product complexity scale.
• Identify and address technical debt.
• Design and ship production-grade agentic workflows with robust state management, failure handling, and human-in-the-loop checkpoints.
• Evaluate and integrate orchestration frameworks.
• Build control planes for enterprise clients providing visibility, auditability, and governance over AI behavior.
• Own prompt architecture, model selection, token economics, and output reliability at scale.
• Stay current on the enterprise agentic stack and critically assess new tooling.
• Define and own Bold AI's compliance posture: data handling, residency, encryption, access control, audit trail, and incident response.
• Architect for enterprise-grade compliance across Bold AI's platform and client deployments, including SOC 2, ISO 27001, and sector-specific obligations.
• Act as the technical interlocutor for client InfoSec, legal, and procurement teams during enterprise due diligence.
• Set the IP boundary architecture for client ownership of agents and data while protecting Bold AI's intellectual property.
• Demonstrate strategic front room leadership, translating architecture into business decisions for non-engineers.
• Represent Bold AI as the senior technical voice in steering committees, sales conversations, and post-mortem reviews.
• Lead, mentor, and set the technical standard for a team of engineers and an automation lead.
• Own code review culture, deployment practices, and engineering quality across the team.
• Partner with the Product Lead to translate strategy into a scoped, sequenced roadmap.

Requirements

• 10+ years in engineering, with 3+ years building and operating AI and LLM systems in production.
• Hands-on experience designing and shipping enterprise agentic solutions in regulated or enterprise environments.
• Deep technical judgment on LLM selection, orchestration trade-offs, harness patterns, control plane design, and infrastructure decisions.
• Demonstrated strategic front room leadership with confidence, credible as the senior technical voice in enterprise client conversations across executive, InfoSec, legal, and procurement audiences.
• Track record leading and growing a small engineering team while remaining a strong individual contributor.
• Experience setting and operating an enterprise-grade compliance and security posture across infrastructure and client deployments.

Skills

• AI and LLM systems
• Enterprise agentic solutions
• LLM selection
• Orchestration trade-offs
• Harness patterns
• Control plane design
• Infrastructure decisions
• Strategic front room leadership
• Enterprise client conversations
• Team leadership
• Compliance and security posture

Location

• Toronto-based
• Remote across Canada

Work Type

• Full-time

Experience Level

• Senior
• 10+ years in engineering
• 3+ years building and operating AI and LLM systems in production

Salary/Compensations

• Compensation includes upside. Range and structure to be discussed.

About the Company

• Bold AI is an applied AI company in active scale, delivering structured transformation engagements grounded in their PIE methodology and the four-mode AI arc (Assistants, Co-Pilots, Agents, Autopilots).
• Deployments are built on Microsoft Azure and Copilot Studio, shipped through Microsoft Teams.
• Clients span various industries including financial services, commercial real estate lending, consumer electronics, large-scale produce growers, sporting goods and apparel, retirement community operators, and enterprise events.
• Deployments occur across regulated industries where compliance and IP ownership are critical.
• Bold AI is a small, fast-moving team.