Manager, Outbound Sales Development - Square

Block; Remote; CAD 80,000 - 100,000; Full time

Job summary

A leading financial technology company is seeking a Manager of Outbound Sales Development to drive outbound pipeline generation in Toronto, Ontario. In this role, you will lead Business Development Representatives and focus on improving first interactions and outbound prospecting. The ideal candidate will have 3+ years in Sales Development, a proven track record of leading teams, and a commitment to creating a high-performance culture. This position offers a remote work option and opportunities for professional growth.

Qualifications

• 3+ years in Sales Development or outbound sales, including 1+ year in leadership.
• Proven track record of leading high-performing teams.
• Deep expertise in outbound motions and multi-channel outreach.

Responsibilities

• Own the outbound engine and strategy.
• Exceed pipeline targets and deliver strong performance.
• Develop and mentor team members for effective execution.

Skills

Sales Development

Leadership

Business Development

Data-driven mindset

Tools

Salesforce

Outreach

Job description

Manager, Outbound Sales Development - Square

Remote Toronto, Ontario, Canada Req ID: R0005307 Posted 10 days ago

Square is seeking a high-impact Manager, Outbound Sales Development 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.

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.

We’re building a team that competes hard, moves fast, and wins — and your leadership will set the tone.

You will:

Outbound Strategy & Execution

• 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.

Leadership & Team Development

• 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.

You have:

• 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

Pay Transparency

Block takes a market‑based approach to pay, and pay may vary depending on your location. U.S.-locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate's starting pay will be determined based on job‑related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

To find a location's zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information.

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.