Chief Technology Officer driving AI-first architecture, agentic engineering, and distributed team execution at Toptal. Owning technical strategy, hiring, platform reliability, and production AI outcomes.
Responsibilities
Drive execution for Toptal’s product and engineering teams and put AI at the core of company development
Own Toptal’s full technical architecture and build it AI-first using agentic engineering practices
Create and own AI architecture and company-wide AI engineering best practices
Lead initiatives that put agents into production
Set technical direction and turn strategy into production-ready outcomes
Own the technical architecture of all Toptal products
Collaborate with Product to design infrastructure exposing core business logic through modular interfaces
Own resourcing and workforce planning, including scoping work, sizing teams, planning headcount, and defining roles
Hire high-performing team members and establish role-specific standards
Set team standards, develop people, and assess performance against those standards
Coach engineers on agentic best practices and advise executives on new AI capabilities
Own AI technology strategy, including model selection, fine-tuning, harness design, orchestration, retrieval, context engineering, tool and MCP integration, guardrails, evaluation, and cost control
Deploy agentic engineering across matching, vetting, onboarding, delivery, and internal operations
Own AI evaluations, regression suites, review loops, and measurable quality
Improve engineering output through AI-assisted development, review, testing, and operations
Own end-to-end architecture, services, data flows, interfaces, and system boundaries
Own throughput, reliability, platform architecture, build-versus-buy decisions, technical debt, secure-by-design architecture, responsible AI, and engineering/AI costs
Establish an execution rhythm with the CEO and assess engineering and AI maturity
Present strategy, resourcing plans, and accountability frameworks to the executive team
Stand up shared AI architecture and evaluations and put agentic workflows into production
Demonstrate business impact from agents in at least two core workflows within six months
Build an advanced engineering organization with AI embedded in its architecture and operating model
Requirements
Bachelor’s degree in Computer Science, Engineering, or a related technical field is required
15+ years of progressive engineering leadership, including significant time as a CTO or VP of Engineering, or as a direct report to one at meaningful scale
Deep, current, hands-on command of modern AI engineering, including foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation
Experience shipping and operating AI systems in production
Knowledge of building and fine-tuning foundation models from the ground up
Experience deploying agentic systems at scale against real business processes, with measured outcomes on cost, cycle time, quality, or revenue
Rigor about model, prompt, and agent evaluation, with evidence-based improvement measurement
Command of model routing, hosted versus self-hosted infrastructure, inference capacity, latency and cost budgets, and provider portability
Proven ability to teach AI and move an organization toward adopting new technology
Strategy creation based on evidence rather than authority
Proven ownership of resourcing and workforce planning, with a quantifiable hiring track record
Currently hands-on; able to read and write code and identify flaws in design documents or evaluation harnesses
Command of distributed systems, service architecture, data-intensive applications, and cloud infrastructure at scale
Experience scaling and modernizing a large existing codebase without stopping the business
Experience leading a globally distributed, remote team at a technology or hyper-growth company is required
Outstanding written and verbal communication skills
World-class individual contributor capability
Resumes and communication must be submitted in English
Benefits
Fully remote work arrangement
Global, borderless work environment
Support structure encouraging innovation, social interaction, and fun
⚙️ We’re Hiring - Jr. Project Control Officer⚙️ We’re looking for a highly organized Project Control Officer to support implementation teams with scheduling, me
I am looking for an experienced Project Control Officer for a top financial bank located in the heart of Downtown Toronto! What you’ll be doing: Owning project
We’re Hiring: Junior Technology Logistics Support Associate 📍 Location: Calgary, AB onsite 💼 Role Type: Contract 6 - 12 months Are you an IT professional who thri
URGENT **2 Junior Project Control Officers (PCO) 88 Thomas Technology Partners Inc. (TTP) is seeking 2 Junior Project Control Officers to support a large - scale
📢 We’re Hiring: Jr. Project Control Officer Stafingo is looking for a Jr. Project Control Officer to support Emergency Services implementation teams in a public
Lead financial reporting, budgeting, and accounting operations for a growing Canadian professional services organization, providing strategic insight to senior leadership.
Directeur.trice technique chez GSM Studios, créateur d’expériences narratives et immersives, expositions muséales et attractions touristiques. Pilotage de la faisabilité, du prototypage, des budgets et des installations techniques à Montréal.
Field CTO advising enterprise leaders and strategic customers on 1Password’s identity security platform. Shaping Solutions Engineering, product strategy, and executive engagement across the US and Canada.