Director of Field Sales - Northeast Region

Company Overview

Since its founding in 2009, Square has evolved alongside the commerce landscape, moving from simple payment processing to offering a comprehensive suite of integrated software solutions. These tools assist sellers in managing their businesses online and offline—from inventory and appointments to payment options and financial services like loans. Through platforms such as Afterpay, Square continues to help businesses grow by enabling innovative omnichannel buying experiences.

Role Summary

We are seeking a motivated and entrepreneurial leader to oversee and expand our Field Sales team throughout the Northeast Region. This pivotal role requires a blend of startup agility and operational excellence to nurture a high-performing sales organization focused on Small and Medium-sized Businesses (SMBs). You will spearhead strategies, lead sales managers and account executives, and embody deep expertise in our product ecosystem while fostering a culture grounded in agility and competitiveness.

Key Responsibilities

• Expand and refine the Northeast Field Sales operations by optimizing territory structures and go-to-market strategies with disciplined execution.
• Establish a high-performance culture emphasizing accountability, competition, and consistent target achievement.
• Lead actively by spending substantial time in the field, co-selling, coaching, and demonstrating comprehensive product knowledge.
• Maintain expert-level understanding of Square’s complete product suite and ensure consultative sales tied directly to customer outcomes.
• Deliver data-driven growth by closely managing sales pipelines, conversion metrics, and overall sales productivity.
• Continuously enhance sales tools and processes to increase efficiency and scalability.
• Collaborate cross-functionally with marketing, operations, partnerships, and product teams to align regional initiatives with national objectives.
• Identify, develop, and retain talented sales professionals passionate about excellence and career growth.
• Act as a local ambassador for Square’s mission and brand, engaging with business leaders and communities across the Northeast.

Candidate Profile

• Minimum 10 years of sales experience, including at least 5 years managing regional or field sales teams within fast-growing SaaS, fintech, or payment technology environments.
• Proven track record of exceeding revenue and productivity targets regionally.
• Demonstrated ability to build and maintain coaching-driven, high-achievement sales cultures.
• Strong product acumen with the ability to position multiple complex products strategically, using data to inform decisions.
• Resourceful, fast-moving professional with experience effectively scaling operational processes.
• Skilled in forecasting, pipeline analytics, and monitoring key performance indicators.
• Outstanding communication skills and presence, capable of influencing all organizational levels.

Compensation and Equal Opportunity

Compensation is market-based and varies by location within four pay zones across the U.S., ranging between $304,000 to $456,000 annually, including target variable components. We commit to fair and inclusive hiring, evaluating candidates without bias and accommodating applicants throughout the recruitment process.

Additional Information

We employ AI-assisted tools during recruitment to ensure consistent and efficient evaluation while complying with privacy and anti-bias regulations. Our benefits package supports work-life balance with options for remote work, health insurance, flexible time off, retirement plans, and family planning resources.