Director of Field Sales, Central Region

About the role

Block is seeking a strategic sales leader to manage and expand our Field Sales organization within the Central Region. This role requires an entrepreneurial mindset to drive growth, mentor sales teams, and operationalize our go-to-market strategy for small and midsize businesses. The successful candidate will own the end-to-end performance of the central territory, setting the vision and execution plan for sales success. You will be responsible for fostering a culture of accountability, innovation, and relentless focus on exceeding revenue and productivity objectives. This position demands a hands-on approach where you will actively participate in selling and coaching to ensure team alignment with best practices. You will serve as the primary strategist for your region, translating corporate objectives into actionable plans for your team. Your work will directly influence the market penetration and brand strength of Block's solutions in a highly competitive landscape. By leveraging data and market insights, you will continuously refine the approach to capturing new business opportunities.

Key facts

What you'll do

• Refine territory models and go-to-market plans to scale the regional organization for future demands.
• Cultivate a high-performance culture focused on accountability, coaching, and exceeding revenue targets through consistent reinforcement.
• Engage in field work, including co-selling alongside reps and coaching in real time, to demonstrate product expertise and close difficult deals.
• Manage pipeline health, sales productivity, and conversion metrics using sophisticated data-driven insights to inform critical decisions.
• Improve sales systems, tools, and playbooks to increase efficiency, remove friction, and standardize successful methodologies.
• Collaborate with Marketing, Sales Ops, Partnerships, and Product teams to align regional execution with national goals and feedback loops.
• Recruit, interview, and develop top-tier sales talent, ensuring the team reflects the highest standards of professionalism and skill.
• Act as the local representative for the Square brand and mission, building trusted relationships with key stakeholders in the community.
• Analyze competitive dynamics and market trends to adjust strategies and maintain a decisive advantage in the Central Region.
• Drive the adoption of new product features and updates, ensuring the sales team can articulate value to diverse customer segments.
• Establish rigorous forecasting processes to predict revenue accurately and guide resource allocation effectively.
• Lead cross-functional initiatives that solve complex client problems using integrated solutions from the Block ecosystem.
• Develop and maintain strategic account plans for key clients to ensure retention, expansion, and long-term loyalty.
• Champion the use of data analytics to identify bottlenecks and optimize the entire sales funnel from prospecting to renewal.

Requirements

• 10+ years of sales experience with a consistent history of achieving and surpassing demanding quotas.
• 5+ years of experience leading regional or field sales teams in fintech, SaaS, or payments with demonstrable success.
• Proven track record of exceeding regional revenue and productivity goals over multiple fiscal periods.
• Expertise in forecasting, KPI tracking, and pipeline management to drive predictable growth and outcomes.
• Ability to position complex, multi-product solutions consultatively to executive-level stakeholders with clarity and confidence.
• Strong executive presence and communication skills to inspire trust and influence at all organizational levels.
• Demonstrated ability to operate autonomously in a fast-paced, matrixed environment with minimal direct supervision.
• Commitment to ethical sales practices and compliance with all regulatory requirements governing financial services.

Skills & tools

• Sales strategy and operations to design and implement scalable growth initiatives.
• Pipeline management to optimize deal progression and reduce cycle times effectively.
• Team leadership and coaching to develop talent and elevate individual performance metrics.
• Data analysis for sales performance to extract actionable insights and drive strategic pivots.
• Consultative selling to uncover client needs and deliver tailored Block solution architectures.

Practical notes

• Compensation is market-based and varies by location zone, reflecting the cost of labor and living in the designated area.
• Candidates may submit a maximum of 9 active applications per 60-day period to ensure a manageable review process.
• Reapplications for the same role are permitted 90 days after a previous review to allow for growth or updated candidacy.
• Automated AI tools may be used during the application evaluation process to screen for initial qualifications.
• Benefits include remote work options, medical insurance, flexible time off, retirement savings, and family planning support to promote work-life integration.
• This role may require travel to meet key objectives and engage with the Central Region market directly.
• Full-time engagement is expected with a standard schedule aligned with business needs and team collaboration hours.
• Candidates must be authorized to work in the United States of America without sponsorship for this position.