Senior Field Sales Leader: Growth, Coaching & Territory Wins

Block; California; On-site; USD 184,000 - 276,000; Full time

Benefits offered by this job

Medical insurance

Retirement savings plans

Flexible time off

Remote work options

Job summary

Block in Orange County seeks a senior field sales leader with a proven track record in high-transaction SaaS or financial services sales. You will coach, recruit, and scale a team of Territory Account Executives, blending in-person and outbound strategies to drive disciplined pipeline and revenue growth.

You will lead from the front, building a high-performance culture through hands-on coaching, rigorous KPI management, and cross-functional alignment with product and marketing to win market

Qualifications

• 8+ years of sales success.
• 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.

Responsibilities

• Develop Territory Account Executives through active, in-market coaching.
• 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.
• Hire, onboard, and develop AEs to ramp quickly, deepen product expertise, and consistently exceed quota.
• Scale what works: build scalable field sales motions and refine go-to-market strategies across key cities.

Skills

Sales leadership

Field sales

SaaS sales

Executive communication

Coaching & mentoring

Cross-functional collaboration

Performance metrics

Industry knowledge

Job description

Block in Orange County seeks a senior field sales leader with a proven track record in high-transaction SaaS or financial services sales. You will coach, recruit, and scale a team of Territory Account Executives, blending in-person and outbound strategies to drive disciplined pipeline and revenue growth.

You will lead from the front, building a high-performance culture through hands-on coaching, rigorous KPI management, and cross-functional alignment with product and marketing to win market