Square Offices

Own the architecture and technical strategy for Square’s go-to-market systems. Build and operate production AI agents, automated workflows, and integrations that improve sales productivity. Lead complex initiatives through architecture, implementation, testing, deployment, and operations while establishing AI evaluation, observability, security, reliability, and human-oversight practices. Partner with Sales, Product, Data, and Engineering leaders to translate business needs into scalable solutions, make build-versus-buy decisions, mentor engineers, and improve business impact through data and user feedback.

Leads sales compensation operations, including quota and crediting processes, commission calculations, data pipelines, audits, controls, governance, and payout accuracy. Manages and develops a high-performing team while administering Pigment and Salesforce, improving automation and data integrity, resolving exceptions, and partnering with Sales, Finance, and Revenue Operations leadership. Requires strong analytical, systems, stakeholder-management, and sales compensation expertise.

Leads quota, capacity, and headcount planning across Block’s commercial sales organizations. Builds scalable planning methodologies, systems, data, governance, and processes; owns quota-setting and hiring models; conducts scenario planning; and advises Sales and Finance executives on growth investments. Partners with Compensation Design, Recruiting, Strategy, and Operations to align assumptions, incentives, role mix, hiring timing, productive capacity, and performance management across direct, channel, advertising, media, and account management motions.