Manager, Field Sales - Toronto
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Key skills for this role
About the Role
Block (Square) is looking for a Manager, Field Sales to lead a high-accountability field sales organization in Toronto. You will develop Territory Account Executives through active coaching, manage pipeline and KPIs, and build a high-performance culture.
Key Skills for This Role
Responsibilities
- Lead with expertise in the field: develop Territory Account Executives through active coaching in sourcing, discovery, positioning, and closing.
- Model world class selling by joining prospect and customer meetings.
- Spend significant time in the field strengthening local relationships and fueling community driven pipeline creation.
- Manage pipeline and KPIs with rigor: diagnose gaps, identify risks, and guide AEs to create high quality opportunities.
- Run disciplined weekly pipeline, forecast, and deal reviews.
- Use data backed insights to coach AE effectiveness and elevate sales execution.
- Build a high performance, high accountability culture defined by trust, clear expectations, and ownership.
- Hire, onboard, and develop AEs to ramp quickly and consistently exceed quota.
- Become a product and competitive expert; build scalable field sales motions.
- Champion the customer voice and collaborate cross functionally to strengthen product market fit.
Requirements
- 8+ years of sales success, ideally in a high growth environment
- 5+ years of leadership experience, preferably managing field account executives
- Experience in high transaction SaaS or financial services sales
- Strong bias toward action and experimentation
- Track record of building a winning, high performing culture through hands on leadership and coaching
- Extensive experience operating in a metrics driven sales organization
- Proven ability to influence and collaborate with cross functional partners
- Experience scaling and overseeing large Field Sales teams
- Strong ability to communicate and build relationships with senior executives
- Excellent interpersonal, leadership, organizational, and communication skills
Full Job Posting
Company Overview
- Square enables anyone to take payments and has expanded into integrated, omnichannel solutions for sellers of all sizes.
- We embed financial services tools at the point of sale and are building a significant, meaningful, and lasting business.
The Role
- Square is building a world class, high accountability field sales organization and is looking for a leader who is both a coach and a builder.
- You will be the driving force behind a disciplined, insight led sales motion blending in person selling with proactive outbound strategy.
You Will
- Lead with expertise in the field: develop Territory Account Executives through active coaching.
- Model world class selling by joining prospect and customer meetings.
- Spend significant time in the field strengthening local relationships and fueling pipeline creation.
- Manage pipeline and KPIs with rigor: diagnose gaps, identify risks, and guide AEs.
- Run disciplined weekly pipeline, forecast, and deal reviews.
- Use data backed insights to coach AE effectiveness.
- Build a high performance, high accountability culture.
- Hire, onboard, and develop AEs to ramp quickly and exceed quota.
- Become a product and competitive expert; build scalable field sales motions.
- Champion the customer voice and collaborate cross functionally.
You Have
- 8+ years of sales success, ideally in a high growth environment.
- 5+ years of leadership experience, preferably managing field account executives.
- Experience in high transaction SaaS or financial services sales.
- Strong bias toward action and experimentation.
- Track record of building a winning, high performing culture through hands on leadership.
- Extensive experience operating in a metrics driven sales organization.
- Proven ability to influence and collaborate with cross functional partners.
- Experience scaling and overseeing large Field Sales teams.
- Strong ability to communicate and build relationships with senior executives.
- Excellent interpersonal, leadership, organizational, and communication skills.
Compensation
- Zone A: $202,000—$304,000 CAD (includes target variable compensation).
- Zone B: $202,000—$304,000 CAD (includes target variable compensation).
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