# Staff Software Engineer, Go-to-Market Systems & AI

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** GTM Engineering
**Salary:** CA$223k – CA$334k/yr
**Experience:** 7+ years
**Skills:** Go-To-Market Systems, Artificial Intelligence, AI Agents, LLMs, Tool Calling, Retrieval, Workflow Orchestration, System Design, Software Engineering, Observability, Ai Evaluation, Crm Systems, Data Services, Production Operations
**Posted:** 2026-08-31

> Leads architecture and hands-on delivery of AI-powered go-to-market systems that automate sales workflows and improve productivity. Requires staff-level technical leadership, production AI experience, strong system-design skills, and substantial engineering experience.

## Job Description

## Responsibilities
- 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 reduce manual sales work and improve decision-making.
- Lead technical execution across initiatives by setting direction, decomposing complex problems, reviewing designs, and supporting high-quality delivery.
- Remain hands-on across prototyping, architecture, implementation, testing, deployment, and production operations.
- Partner with Sales, Sales Strategy & Operations, Product, Data, and Engineering leaders to translate business problems into scalable solutions.
- Establish evaluation methods, patterns, and guardrails for reliable, observable, secure, and safe AI systems handling sensitive business data.
- Define success measures and use data, evaluations, and user feedback to improve accuracy, adoption, and business impact.
- Make build-versus-buy decisions and guide integrations across internal platforms, CRM systems, data services, and third-party tools.
- Build alignment with senior technical and business partners, communicate tradeoffs, mentor engineers, and raise engineering standards through design reviews.

## Requirements
- 12+ years of related experience with a bachelor's degree; or 8+ years with a master's degree; or a PhD with 5+ years of experience; or equivalent experience.
- Experience setting technical direction and delivering complex, business-critical systems across multiple teams or functional areas.
- Experience designing, building, and operating production software using large language models, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
- Track record of moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
- AI-native engineering approach, with sound judgment about when to use models, deterministic software, or human review.
- Strong software engineering and system-design skills across application, service, integration, and data layers.
- Experience leading technical execution through influence, mentorship, architecture, and direct contribution without formal reporting authority.
- Ability to navigate ambiguity, evaluate technical and business tradeoffs, and influence senior engineering and business partners.

## Nice to Have
- Familiarity with sales processes or go-to-market systems, including lead management, opportunity management, forecasting, account planning, or customer relationship management platforms.

## Compensation and Benefits
- Annual salary range of $222,900–$334,300 CAD.
- Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning support.

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