Impress employers and recruiters.
Choose from hundreds of resume examples.

Target Resume Now

Tailor your resume to this Staff Software Engineer, Go-to-Market Systems & AI role.

Rezi rewrites your resume against Block's job description. Free.

Resume score gauge reading 58 out of 100

Don't guess if your resume is good enough.

See how it scores against the Staff Software Engineer, Go-to-Market Systems & AI posting at Block — free, in seconds.

About the Role

The Go-to-Market Engineering team builds systems, automations, and AI-powered experiences to help sales teams focus on serving customers. As a Staff Software Engineer, you will be the technical owner of the go-to-market technology stack, defining its architecture and long-term direction while leading engineers through complex sales challenges. You will collaborate with Sales, Sales Strategy & Operations, Product, Data, and Engineering leaders to deliver scalable solutions that enhance sales productivity and business performance.

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 to reduce manual sales work, improve decision-making, and free up sales teams' time.
Lead technical execution across initiatives of varying sizes by setting direction, breaking down complex problems, reviewing designs, and helping engineers deliver high-quality solutions.
Remain hands-on throughout the software lifecycle, including prototyping, architecture, implementation, testing, deployment, and production operations.
Partner with Sales and Sales Strategy & Operations to understand workflows, identify high-value opportunities, and translate business problems into scalable technical solutions.
Establish patterns, evaluation methods, and guardrails for building reliable, observable, secure, and safe AI systems for sensitive business data.
Define success measures and use data, evaluations, and user feedback to improve the accuracy, adoption, and business impact of new capabilities.
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 complex tradeoffs clearly, and raise engineering standards through mentorship and design reviews.

Requirements

A minimum of 12 years of related experience with a Bachelor’s degree; or 8 years and a Master’s degree; or a PhD with 5 years 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 that uses large language models, AI agents, tool calling, retrieval, workflow orchestration, or related technologies.
A track record of moving AI capabilities from prototype to production, including evaluation, observability, security, reliability, and human oversight.
An AI-native approach to engineering, using AI tools throughout development while applying sound judgment about when to use models, deterministic software, or human review.
Strong software engineering and system-design skills, with the ability to work hands-on across application, service, integration, and data layers.
Experience leading technical execution through influence, mentorship, architecture, and direct contribution, without relying on formal reporting authority.
The judgment to navigate ambiguous problems, evaluate technical and business tradeoffs, and influence senior engineering and business partners.
Familiarity with sales processes or go-to-market systems—such as lead management, opportunity management, forecasting, account planning, or customer relationship management platforms—is helpful but not required.

Skills

Large language models
AI agents
Tool calling
Retrieval
Workflow orchestration
Software engineering
System design
Application layer
Service layer
Integration layer
Data layer

Location

Canada

Work Type

Remote

Experience Level

Staff

Education Level

Bachelor's degree
Master's degree
PhD

Salary/Compensations

$222,900—$334,300 CAD

Benefits

Remote work
Medical insurance
Flexible time off
Retirement savings plans
Modern family planning

About the Company

Since opening in 2009, Square (now Block) has evolved commerce by enabling anyone to take payments and never miss a sale. They expanded into software to build integrated, omnichannel solutions for sellers, covering online sales, inventory management, buy now, pay later, appointment booking, customer engagement, and staff management. Financial services are embedded at the point of sale, providing merchants with business loans and cash flow management. Afterpay further enhances their goal of providing omnichannel tools that unlock value and growth for sellers. Block partners with sellers of all sizes, from large enterprises to startups, and their solutions grow with their customers. They are building a significant, lasting business and helping sellers worldwide do the same. Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy through brands like Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, aiming to build a financial system open to everyone.

Equal Opportunity

Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. They consider qualified applicants with criminal histories for employment on their team, assessing candidates on an individualized basis. They are committed to an inclusive interview experience, including providing reasonable accommodations. They strive to live by the values of building a more inclusive economy where customers have equal access to opportunity.