Manager, Field Sales at Block. About the role Block is on the lookout for an experienced leader to take charge of a dynamic field sales team for Square. This position emphasizes the importance of coaching Territory Account Executives through hands‑on engagement in the market while fostering a disciplined, data‑oriented sales culture. Your primary objective will be to drive revenue growth by exemplifying effective selling techniques and refining strategies tailored to the Toronto market.

Key facts

• Location: Toronto, Ontario, Canada
• Engagement: Full‑time
• Salary: $202,000 - $304,000 CAD (includes target variable compensation)

What you’ll do

• Provide hands‑on coaching to Territory Account Executives throughout the entire sales process, from initial outreach to deal closure.
• Actively participate in meetings with prospects and clients to showcase product value and offer immediate feedback.
• Oversee the sales pipeline and key performance indicators (KPIs) by identifying performance gaps and conducting weekly reviews of ongoing deals.
• Recruit, onboard, and mentor team members to ensure they achieve their sales targets and maintain a high level of product knowledge.
• Develop scalable field sales playbooks and operational rhythms designed to enhance market presence and share.
• Collaborate with cross‑functional teams and local networks to boost brand visibility and generate leads.
• Analyze market trends and competitor activities to inform sales strategies and tactics.
• Foster a culture of accountability and continuous improvement within the sales team.
• Utilize data analytics to measure performance and drive decision‑making processes.
• Ensure that the team is equipped with the necessary tools and resources to succeed in their roles.
• Implement training programs that focus on skill development and sales excellence.
• Maintain open lines of communication with upper management regarding team performance and market insights.

Requirements

• A minimum of 8 years of experience in sales, ideally within rapid‑paced, high‑growth environments.
• At least 5 years of experience in a leadership role, specifically managing field sales teams.
• A solid background in high‑volume SaaS or financial services sales is essential.
• Demonstrated ability to scale and manage large field sales teams effectively.
• Experience working in a metrics‑driven sales organization is crucial.
• Exceptional communication skills, with a proven ability to build relationships with executives and key stakeholders.
• Strong analytical skills to interpret data and make informed decisions.
• A track record of achieving sales targets and driving revenue growth.

Nice to have

• Experience with CRM software and sales enablement tools.
• Familiarity with digital payment solutions and financial technology.
• Previous experience in a startup or rapidly changing environment.
• Knowledge of the Toronto market and its unique challenges.
• A network of contacts within the local business community.

Skills & tools

• Proficient in managing sales pipelines and forecasting revenue.
• Expertise in consultative selling techniques and competitive positioning.
• Ability to develop effective field sales strategies that align with company goals.
• Strong data analysis skills for performance coaching and strategy refinement.
• Familiarity with sales automation tools and customer relationship management (CRM) systems.

Practical notes

• Block offers a range of benefits, including options for remote work, comprehensive medical insurance, flexible time off policies, retirement savings plans, and support for family planning.
• Candidates are allowed to have a maximum of 9 active applications within any 60‑day period.
• Reapplications are welcome after a 90‑day interval following a previous application review.
• The hiring process may incorporate automated AI tools to assist in evaluating applications.

This role at Block presents an exciting opportunity for a driven sales leader to make a significant impact in the Toronto market.