Manager, Outbound Sales Development (SaaS)

TL;DR

Manager, Outbound Sales Development (SaaS): Leading the Mid-Market Sales Development function to build the outbound pipeline for mid-market merchants with an accent on sequencing strategy and team coaching. Focus on designing outbound prospecting strategies, optimizing qualification frameworks, and driving pipeline conversion for complex sales cycles.

Location: Must perform work within Ontario, Canada

Salary: $130,000 - $150,000 CAD

Company

A one-stop commerce platform that helps merchants innovate to simplify, scale, and provide exceptional customer experiences globally.

What you will do

• Design and execute outbound prospecting strategies targeting mid-market merchants ($2M–$50M GMV).
• Build multi-channel sequencing (email, phone, LinkedIn) tailored to longer buying cycles and multiple stakeholders.
• Hire, onboard, and coach a team of Mid-Market SDRs, focusing on discovery quality and objection handling.
• Own the end-to-end qualification process and refine ICP criteria based on conversion data and feedback.
• Partner with Account Executives and Marketing to align handoff quality, lead scoring, and messaging.
• Monitor pipeline health metrics and report on performance, contribution, and capacity planning.

Requirements

• 3–5+ years in sales development or outbound sales, with at least 2 years in a people management role.
• Proven experience running mid-market or enterprise SDR motions with long sales cycles (60–120+ days).
• Strong understanding of account-based selling, multi-threading, and stakeholder mapping.
• Proficiency with Salesforce and sales engagement platforms such as Outreach or Salesloft.
• Fluency in English as a working language.
• Must be based in Ontario, Canada.

Nice to have

• Background in B2B SaaS, POS, e-commerce, or retail technology.
• Experience working with wholesale or retail merchant ecosystems.
• Familiarity with the NuORDER or Lightspeed platform.

Culture & Benefits

• Flexible work environment with remote work policies.
• Equity options and contributions to a pension plan.
• Comprehensive health and wellness credits, including medical, dental, life, and disability insurance.
• Flexible paid time off and enhanced parental leave.
• Continuous learning and training opportunities for professional growth.
• Computer purchase program for a personal Macbook.