Manager, Outbound Sales Development - Square

Block is seeking a high-impact Manager, Outbound Sales Development to lead and scale outbound pipeline generation for Square. This role involves overseeing a team of Business Development Representatives, shaping outbound strategy, and ensuring high-performance in execution and conversion.

Responsibilities:

• Own the outbound engine: Define and drive the strategy, execution, and continuous improvement of outbound pipeline generation
• Exceed pipeline targets: Consistently deliver strong SQL, meeting, and conversion performance with high-quality output
• Sharpen outbound execution: Review cold calls, emails, and cadences to refine talk tracks, personalization, sequencing, and objection handling
• Improve conversion: Identify funnel gaps, diagnose root causes, and implement changes that increase meeting quality and downstream pipeline conversion
• Competitive positioning: Train the team to position Square’s integrated ecosystem as the modern, efficient, high-value alternative in the market
• Forecasting & reporting: Own pipeline forecasting and deliver clear, data-backed insights to Sales leadership
• Territory and ICP alignment: Collaborate across Sales, Marketing, and Sales Ops to refine ICP, prioritize accounts, and optimize outbound coverage
• Experiment & scale: Test new messaging, channels, and tactics. Operationalize what works; eliminate what doesn’t
• Develop elite outbound talent: Coach and mentor BDRs across call execution, active listening, objection handling, and qualification discipline
• Build a performance culture: Create a metrics-driven environment grounded in accountability, consistency, and continuous improvement
• Operational excellence: Implement scalable onboarding, coaching frameworks, and performance management systems that support rapid growth
• Cross-functional alignment: Partner closely with Sales Enablement and Marketing to ensure outbound campaigns and plays land with precision
• Data-driven management: Use Salesforce, Outreach, and analytics tools to inspect activity, monitor conversion trends, and drive targeted coaching

Requirements:

• 3+ years in Sales Development, Business Development, or outbound sales, including 1+ year in a leadership or coaching capacity
• Proven track record of leading high-performing teams that exceed outbound pipeline targets
• Deep expertise in outbound motions—cold calling, sequencing, messaging, objection handling, and multi-channel outreach
• Demonstrated ability to build, coach, and scale high-output teams that operate with urgency and discipline
• A data-first mindset with strong forecasting, operational rigor, and process-management skills
• Exceptional communication and leadership presence—you set clear expectations, rally teams, and drive results