Remote Senior Sales Manager – High-Performance Outbound Team

Block, Inc.; Toronto; Remote; CAD 172,000 - 257,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Modern family planning

Job summary

Block, Inc. in Canada (Ontario) is seeking a Senior Sales Manager to lead a high-performance outbound team and develop top talent. You will coach Account Executives, refine playbooks, and drive data-informed decisions to improve pipeline health and revenue growth.

You will partner with Marketing, Enablement, Operations and Product to optimize the customer journey, elevate forecast accuracy, and implement scalable processes across a growing organization.

Qualifications

• 7+ years experience as a sales manager.
• 3 years of documented sales success as an individual contributor exceeding target.
• Proven track record leading high-performing sales teams in a fast-paced, high-growth environment.
• Experience leading an outbound-led team, with ICP targeting, multi-channel approach, and pipeline quality focus.
• Success developing Account Executives into top performers through structured coaching and clear expectations.
• Deep expertise in pipeline management, forecasting, and using data to improve outcomes.
• Demonstrated experience hiring exceptional talent and building teams that consistently outperform.
• Strong business judgment balancing short-term execution and long-term health.

Responsibilities

• Build and lead a high-performance sales team.
• Hire exceptional Account Executives and raise the talent bar with every addition.
• Develop a culture of ownership, accountability, continuous learning, and high standards.
• Identify future top performers early and create development plans to accelerate growth.
• Coach through data and business intelligence with pipeline health diagnostics.
• Lead forecasting, pipeline inspection, and performance reviews.
• Use leading indicators to identify gaps and coach for sustainable improvement.
• Turn data into action by diagnosing trends and driving improvements across the team.
• Partner with Sales Leadership, Marketing, Enablement, Operations and Product to improve the customer journey.
• Shape strategy using customer insights and field intelligence and influence product evolution.
• Lead through change by helping teams adapt quickly while maintaining high performance.

Skills

Sales management

Outbound sales

Leadership

Pipeline management

Team coaching

Talent development

Forecasting

Job description

Block, Inc. in Canada (Ontario) is seeking a Senior Sales Manager to lead a high-performance outbound team and develop top talent. You will coach Account Executives, refine playbooks, and drive data-informed decisions to improve pipeline health and revenue growth.

You will partner with Marketing, Enablement, Operations and Product to optimize the customer journey, elevate forecast accuracy, and implement scalable processes across a growing organization.