Operations Lead

Description:

Square, a subsidiary of Block, Inc., is seeking a Canada GTM Strategy & Operations Lead to drive strategy, planning, and execution to fuel business growth in the Canadian market. This role is highly cross-functional and requires close collaboration with Sales, Account Management, Partnerships, Marketing, Product, and Finance teams to define priorities, build scalable go-to-market (GTM) motions, and ensure disciplined execution.

The successful candidate will be responsible for turning market and competitive insights into actionable GTM strategies that accelerate revenue and expand market share. You will lead high-impact initiatives, develop repeatable growth playbooks, partner with Finance on strategic planning, track performance metrics, and ensure teams act decisively on insights to drive results. The role requires strong leadership skills, the ability to align cross-functional teams, and a proven track record of execution in high-growth environments.

Key Responsibilities:

• Develop and execute GTM strategies to expand market share and revenue.

• Prioritize market opportunities and mobilize teams to capture new segments.

• Build and scale playbooks across verticals, partnerships, and channels.

• Lead end-to-end strategic initiatives that solve complex business challenges.

• Co-lead annual, quarterly, and long-range planning processes with Finance.

• Run the rhythm of business reviews, driving accountability and course corrections.

• Define KPIs in partnership with Analytics and Finance; use insights to guide decision-making.

• Build scalable systems, cadences, and processes for GTM execution.

• Serve as a trusted advisor to senior leadership, breaking down silos and enabling alignment.

• Deliver measurable outcomes while ensuring efficient cross-functional collaboration.

Requirements:

• 8+ years of experience in Strategy, Operations, or Consulting (preferably in SaaS, FinTech, or partnerships).

• Strong analytical and problem-solving skills with proven ability to lead strategic initiatives.

• Excellent communication and executive stakeholder management skills.

• Experience in scaling operations and leading through influence.

• Strong bias toward action, ability to navigate ambiguity, and drive results independently.

Benefits:

• Remote work flexibility.

• Comprehensive medical insurance.

• Retirement savings plans.

• Flexible paid time off.

• Family planning support.

• Modern and inclusive workplace with emphasis on diversity and equity.