Manager, Field Sales (French Bilingual)

Block•Montreal, QC

15d•Remote

About The Position

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. The ideal candidate deeply understands the craft of selling, including how to open doors, generate pipeline, position value competitively, and close with precision. This role requires leading from the front, developing the team through active engagement. The Manager will be the driving force behind a disciplined, insight-led sales motion that blends in-person selling with proactive outbound strategy. Their leadership will elevate both the quality and velocity of revenue while shaping a culture rooted in excellence, ownership, and growth. This is a hands-on leadership role for someone with deep product expertise, strong competitive instincts, and a track record of raising the bar for sellers.

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, balanced with thoughtful decision-making
A 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 in a rapidly scaling business
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

Responsibilities

Lead with expertise in the field.
Develop Territory Account Executives through active, in-market coaching — from sourcing and opening conversations to consultative discovery, competitive positioning, and closing with clarity.
Model world-class selling by joining prospect and customer meetings, demonstrating product fluency, value articulation, and decisive deal strategy.
Spend significant time in the field with your team, strengthening local relationships, fueling community-driven pipeline creation, and ensuring sellers experience Square through a human, product-driven presence.
Manage pipeline and KPIs with rigor — diagnosing gaps, identifying risks, expanding coverage, and guiding AEs to create and progress high-quality opportunities.
Run disciplined weekly pipeline, forecast, and deal reviews that drive action, accountability, and predictable outcomes across multiple markets.
Use data-backed insights to coach AE effectiveness, elevate sales execution, and ensure consistent momentum across high-velocity, complex sales cycles.
Create an environment defined by trust, clear expectations, ownership, and open communication.
Hold the team to a high bar of execution while providing the clarity, structure, and hands-on coaching needed to meet it.
Hire, onboard, and develop AEs to ramp quickly, deepen product expertise, and consistently exceed quota.
Become a product and competitive expert — ensuring your team can confidently articulate Square's value and differentiation.
Build scalable, repeatable field sales motions that increase funnel quality, improve outbound productivity, and accelerate growth in your assigned cities.
Continuously refine strategy, playbooks, and operating rhythms to deepen Square's presence and win market share across key local ecosystems.
Champion the customer voice and collaborate cross-functionally to strengthen product-market fit and unlock new revenue pathways.
Engage deeply with community networks, partners, and local events to amplify brand awareness and fuel top-of-funnel opportunity creation.