Field Sales Manager – Toronto

About the role

Square is building a world‑class field sales organization and seeks a hands‑on leader to drive revenue growth in the Toronto market. As a Field Sales Manager you will coach Territory Account Executives, lead by example in client meetings, and shape a high‑performance culture focused on disciplined, insight‑led selling.

Key responsibilities

• Coach and develop Territory Account Executives through the full sales cycle, from prospecting to closing.
• Participate in prospect and customer meetings to model best‑in‑class selling techniques and product articulation.
• Spend significant time in the field to build local relationships, generate community‑driven pipeline, and ensure a human, product‑focused presence.
• Manage pipeline and key performance indicators with rigor, diagnosing gaps and guiding reps toward high‑quality opportunities.
• Run weekly pipeline, forecast, and deal reviews to drive accountability and predictable outcomes.

Required profile

• Proven experience leading field sales teams and delivering consistent revenue results.
• Deep understanding of consultative selling, competitive positioning, and deal strategy.
• Strong coaching mindset with a track record of developing sales talent.
• Ability to operate in a fast‑moving, data‑driven environment.

Required skills

• Expertise in field sales methodologies and pipeline management.
• Strong product fluency to articulate value propositions.
• Excellent communication and negotiation skills.

What we offer

• Opportunity to shape a growing, high‑impact sales organization.
• Collaborative culture focused on ownership, growth, and excellence.
• Competitive compensation and benefits package.