Field Sales Director, Central Region

🇺🇸 Chicago, IL
$3K - $5K Annual
Posted 1 day ago
Expires December 29, 2026
Full TimeRemoteSalesOperationsLegal

The Field Sales Director for the Central Region at Block (Square) is a senior leadership role responsible for scaling and leading the field sales organization across key markets. This position involves managing Sales Managers and Territory Account Executives who focus on acquiring and expanding small and midsize businesses. The role requires a strategic leader who combines entrepreneurial drive with operational discipline to foster a high-performance sales culture.

Key responsibilities include refining territory models, optimizing go-to-market plans, and instilling operational rigor to strengthen the Central Field Sales organization. The director will build a culture grounded in performance, accountability, and competitiveness, motivating teams to exceed targets and celebrate excellence. Spending meaningful time in the field to co-sell, coach, and demonstrate product fluency is essential. Additionally, the director will master Square's ecosystem to ensure teams sell consultatively, connecting product capabilities to seller outcomes.

Candidates should have over 10 years of sales experience, including more than 5 years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment. A proven track record of exceeding regional revenue and productivity goals is essential. Experience in building high-performance teams and creating cultures grounded in coaching, accountability, and excellence is required. Strong product acumen, with the ability to position complex solutions across multiple product lines and use data to guide decisions, is necessary. Operational expertise in forecasting, pipeline management, and KPI tracking is also important.

Compensation for this role ranges from $318,000 to $477,000 annually, including target variable compensation. The exact salary will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Block offers a comprehensive benefits package, including health coverage, paid parental leave, flexible time off, and retirement savings plans.

Block is a global technology company focused on financial services, with brands like Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto. The company builds technology to increase access to the global economy, aiming to make commerce and financial services accessible to sellers of all sizes. Joining Block offers the opportunity to be part of a significant, meaningful, and lasting business that helps sellers worldwide succeed.

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