Strategic Enterprise Sales Leader (Remote)

Block, Inc.; San Francisco (CA); Remote; USD 223,000 - 335,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Family planning

Job summary

Block, Inc. in San Francisco hires an Enterprise Sales Lead, US to lead and scale a team of Enterprise Account Executives, shaping growth for Square, Cash App and Afterpay across the US market.

You will own enterprise pipeline, coach complex deals, and partner with legal, finance, and product teams to drive strategic opportunities and revenue outcomes among top-tier sellers. This role requires a proven leader adept at navigating multi-stakeholder environments.

Qualifications

• 10+ years of enterprise or strategic sales experience with a track record of exceeding targets and closing complex deals.
• 3+ years of people leadership experience.
• Experience leading enterprise teams in platform, SaaS, fintech, payments, data, or commerce environments.
• Experience building pipeline-generation motions including outbound prospecting and partner opportunities.
• Proven ability to build territory, segmentation, and coverage strategies in high-growth markets.
• Experience leading teams through multi-threaded sales cycles involving executive, technical, procurement, legal and finance stakeholders.
• Commercial acumen to coach pricing, negotiation, and deal economics.
• Operational discipline across pipeline management, forecasting, account planning, and deal inspection.

Responsibilities

• Lead and develop Enterprise Account Executives with clear expectations and accountability.
• Generate enterprise pipeline through repeatable, cross-functional motions with Sales Development, Marketing and Partnerships.
• Be accountable for pipeline creation, revenue, and forecast accuracy; ensure successful launches post-signing.
• Establish rigorous operating cadence with regular pipeline reviews and account planning.
• Direct team capacity toward high-potential prospects and ensure alignment with enterprise priorities.
• Coach through complex deals spanning multiple stakeholders to maintain high-quality executions.
• Codify repeatable sales motions for upmarket growth and scalable playbooks.
• Lead strategic deals from the front, opening executive doors and managing negotiations.
• Collaborate with Solutions Engineering, Product, Partnerships, Legal, Finance, Marketing, and Customer Success to move deals forward.
• Turn market insights into business impact by influencing product, pricing, and go-to-market strategy.

Skills

Enterprise sales leadership

People management

Strategic deal coaching

Pipeline generation

Executive engagement

Forecasting & analytics

Deal economics & negotiation

Cross-functional collaboration

Job description

Block, Inc. in San Francisco hires an Enterprise Sales Lead, US to lead and scale a team of Enterprise Account Executives, shaping growth for Square, Cash App and Afterpay across the US market.

You will own enterprise pipeline, coach complex deals, and partner with legal, finance, and product teams to drive strategic opportunities and revenue outcomes among top-tier sellers. This role requires a proven leader adept at navigating multi-stakeholder environments.