# Manager, Field Sales

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Los Angeles, CA, Toronto, Canada
**Role:** Sales Enablement
**Salary:** $164k – $297k/yr
**Experience:** 8+ years
**Skills:** SaaS, Financial Services, Pipeline Management, Sales Forecasting, Sales Coaching, Outbound Sales, Consultative Selling, Competitive Positioning, Account Executive Management, Crm Analytics
**Posted:** 2026-08-11

> Leads and coaches Territory Account Executives in a hands-on field sales organization, driving pipeline quality, forecasting discipline, customer engagement, and quota attainment. Requires 8+ years of sales experience and 5+ years of leadership experience in SaaS or financial services.

## Job Description

## 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.
- Model effective selling by joining prospect and customer meetings, demonstrating product fluency, value articulation, and deal strategy.
- Spend significant time in the field with the team, strengthening local relationships and creating community-driven pipeline.

### Operate in the details
- Manage pipeline and KPIs by diagnosing gaps, identifying risks, expanding coverage, and guiding Account Executives to create and progress high-quality opportunities.
- Run weekly pipeline, forecast, and deal reviews that drive action, accountability, and predictable outcomes across multiple markets.
- Use data-backed insights to coach Account Executive effectiveness and improve sales execution.

### Build a high-performance culture
- Create an environment defined by trust, clear expectations, ownership, and open communication.
- Hold the team to high execution standards while providing structure and hands-on coaching.
- Hire, onboard, and develop Account Executives to ramp quickly, deepen product expertise, and exceed quota.

### Scale sales effectiveness
- Become a product and competitive expert so the team can articulate Square’s value and differentiation.
- Build repeatable field sales motions that improve funnel quality, outbound productivity, and growth in assigned cities.
- Refine strategy, playbooks, and operating rhythms to deepen Square’s presence and win market share.

### Partner across the business
- Champion the customer voice and collaborate cross-functionally to strengthen product-market fit and unlock revenue opportunities.
- Engage with community networks, partners, and local events to amplify brand awareness and fuel top-of-funnel opportunity creation.

## 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.
- 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.

## Compensation and Benefits
- Zone A: **$198,000–$297,000**
- Zone B: **$184,000–$276,000**
- Zone C: **$174,000–$261,000**
- Zone D: **$164,000–$246,000**
- Amounts include target variable compensation.
- Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning.

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