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.
- 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 fast‑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.
- Robust 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, adaptable 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 (Toronto)
🏢 Block
📍 Toronto
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