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.

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📌 Manager, Field Sales (Ontario)
🏢 Block
📍 Ontario