Director of SMB Sales

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Drive substantial new business growth within the SMB sector, ensuring consistent quarterly performance.

• Maintain an average sales cycle of 10 days through disciplined execution.

• Achieve 95%+ forecast accuracy by conducting weekly pipeline inspections.

• Scale predictable revenue while upholding pricing discipline and maximizing value realization and expansion opportunities.

• Build, mentor, and retain a team of over 10 high-performing SMB sellers across North America.

• Design hiring systems, behavior-based coaching methods, ramp programs, and performance frameworks.

• Manage performance and develop future sales leaders.

• Oversee the complete conversion process from lead to opportunity to closed-won.

• Construct pipeline math models and rigorously test capacity planning.

• Establish inspection cadences to identify deal risks.

• Implement SPIN-based discovery techniques and design compensation plans aligned with outcomes.

• Ensure CRM hygiene and maintain data integrity.

• Report business performance with clarity suitable for executive-level and Board presentations.

• Collaborate with Marketing, Customer Success, and Product teams to unlock growth potential.

• Identify and eliminate friction points in the buyer's journey.

• Develop repeatable systems and operational discipline.

• Meet quarterly and annual targets related to SMB revenue, quota attainment, pipeline coverage, retention, forecast accuracy, and leadership development goals.

⛳️ Requirements

• 5+ years of experience in SaaS sales leadership with a demonstrated ability to scale revenue.

• 7+ years of experience in SaaS sales and revenue teams.

• 3+ years managing SMB/Mid-Market sales teams of 10 or more sellers.

• Proven track record of consistently exceeding quotas; membership in the 120%+ club is preferred.

• Mastery of SPIN Selling techniques and behavior-based coaching frameworks.

• Capability to create pipeline math models and manage capacity planning effectively.

• Experience in high-velocity, short-cycle SMB sales; ideally under 30 days.

• Proficiency in CRM analytics, funnel metrics, and revenue operations.

• Exceptional verbal and written communication skills.

• Proficient in English.

• Experience leading SMB sales in vertical SaaS, marketplaces, or multi-product environments is a plus.

• Background in leading technical-oriented products targeting small to medium-sized businesses is a plus.

• Experience designing hiring systems, ramp programs, and performance frameworks from the ground up is a plus.

• Experience in private equity-backed or high-growth companies preparing for exit is a plus.

• A passion for fitness, wellness, or serving entrepreneurs is a plus.

• Strong negotiation and closing abilities for short sales cycles.

• Capacity to thrive in a fast-paced environment and meet tight deadlines.

• Detail-oriented with impeccable follow-up, accountability, transparency, and willingness to provide direct feedback.

🏝️ Benefits

• Open PTO policy.

• Quarterly Days of Disconnect.

• Parental & Pawternity Leave.

• Quarterly fitness reimbursement.

• Medical/Dental/Vision coverage.

• Employee Assistance Program (EAP).

• Calm App subscription for the employee and up to 4 dependents over the age of 16.

• Continuous training and professional development opportunities.

• Bonuses, commissions, equity, or other incentive programs may be available where applicable.