Manager, Outbound Sales Development - Square

<p>Square is seeking a high-impact <strong>Manager, Outbound Sales Development</strong> to lead and scale one of the most critical engines of our GTM motion: outbound pipeline generation. You will oversee a team of Business Development Representatives focused on creating exceptional first interactions, executing high-quality outbound prospecting, and delivering predictable top-of-funnel pipeline for our Sales organization.</p> <p>This is a role for leaders who operate with speed, intensity, and precision. You’ll shape outbound strategy, enforce a high-performance culture, and raise the bar on execution across messaging, sequencing, qualification, and funnel conversion. You’ll partner closely with Sales, Marketing, and Sales Ops to ensure our outbound motion is targeted, competitive, and consistently producing high-velocity results.</p> <p>We’re building a team that competes hard, moves fast, and wins — and your leadership will set the tone.</p> <p><strong>You will:</strong></p> <h3><span style="font-size: 10pt;"><strong>Outbound Strategy Execution</strong></span></h3> <ul> <li><strong>Own the outbound engine:</strong> Define and drive the strategy, execution, and continuous improvement of outbound pipeline generation.</li> <li><strong>Exceed pipeline targets:</strong> Consistently deliver strong SQL, meeting, and conversion performance with high-quality output.</li> <li><strong>Sharpen outbound execution:</strong> Review cold calls, emails, and cadences to refine talk tracks, personalization, sequencing, and objection handling.</li> <li><strong>Improve conversion:</strong> Identify funnel gaps, diagnose root causes, and implement changes that increase meeting quality and downstream pipeline conversion.</li> <li><strong>Competitive positioning:</strong> Train the team to position Square’s integrated ecosystem as the modern, efficient, high-value alternative in the market.</li> <li><strong>Forecasting reporting:</strong> Own pipeline forecasting and deliver clear, data-backed insights to Sales leadership.</li> <li><strong>Territory and ICP alignment:</strong> Collaborate across Sales, Marketing, and Sales Ops to refine ICP, prioritize accounts, and optimize outbound coverage.</li> <li><strong>Experiment scale:</strong> Test new messaging, channels, and tactics. Operationalize what works; eliminate what doesn’t.</li> </ul> <p><strong>Leadership Team Development</strong></p> <ul> <li><strong>Develop elite outbound talent:</strong> Coach and mentor BDRs across call execution, active listening, objection handling, and qualification discipline.</li> <li><strong>Build a performance culture:</strong> Create a metrics-driven environment grounded in accountability, consistency, and continuous improvement.</li> <li><strong>Operational excellence:</strong> Implement scalable onboarding, coaching frameworks, and performance management systems that support rapid growth.</li> <li><strong>Cross-functional alignment:</strong> Partner closely with Sales Enablement and Marketing to ensure outbound campaigns and plays land with precision.</li> <li><strong>Data-driven management:</strong> Use Salesforce, Outreach, and analytics tools to inspect activity, monitor conversion trends, and drive targeted coaching.</li> </ul> <p><strong>You have:</strong></p> <ul> <li>3+ years in Sales Development, Business Development, or outbound sales, including 1+ year in a leadership or coaching capacity.</li> <li>Proven track record of leading high-performing teams that exceed outbound pipeline targets.</li> <li>Deep expertise in outbound motions—cold calling, sequencing, messaging, objection handling, and multi-channel outreach.</li> <li>Demonstrated ability to build, coach, and scale high-output teams that operate with urgency and discipline.</li> <li>A data-first mindset with strong forecasting, operational rigor, and process-management skills.</li> <li>Exceptional communication and leadership presence—you set clear expectations, rally teams, and drive results</ ... (truncated, view full listing at source)