Sales Manager (Player-Coach) - B2B SaaS (Toronto, ON, Canada)

Location
Toronto , ON , CA (remote; open to candidates anywhere in Canada)

Summary

Jolly Technologies is a Silicon Valley-based software company with more than 40,000 customers and millions of users, including many Fortune 500 companies and other world-renowned organizations.

Our products are B2B enterprise, multi-tenant, cloud-hosted SaaS platforms used by organizations of all sizes across North America, Europe, Australia, and worldwide. Depending on business needs, you may work on one or more of our products.

We are looking for a hands-on Sales Manager to lead and grow our sales team. This is a player-coach role: you will carry a personal quota and close deals yourself while managing and coaching our Account Executives, Business Development Representatives, and Solutions Consultants. You will report to the executive team and own the sales process, pipeline, and forecast.

Working Hours

Fully remote, work-from-home contract position. You must work 9:00 AM - 5:00 PM Eastern Time on weekdays , which matches our customer demo hours (6:00 AM - 2:00 PM Pacific Time).

Responsibilities

• Carry a personal quota and close new business, especially larger multi-stakeholder deals
• Manage, coach, and hold accountable a distributed team of Account Executives, BDRs, and Solutions Consultants
• Hire and onboard new sales team members as the team grows
• Build and improve the sales process, from lead qualification and demos through proposals and close
• Own pipeline reviews, forecasting, and sales reporting to the executive team
• Set targets and KPIs for each role and track performance weekly
• Keep the CRM accurate and make it the single source of truth for the team
• Work with marketing on lead quality and with product on customer feedback and feature gaps

Requirements

• 7+ years of B2B SaaS or business software sales experience, including personal success as a closing Account Executive
• 2+ years directly managing Account Executives and/or SDRs/BDRs
• Consistent record of meeting or exceeding quota as both an individual and a manager, with numbers you can share
• Experience selling to organizations in North America, Europe, Australia, or other international markets, including deals with IT, security, and procurement reviews
• Hands-on experience building sales processes, forecasting, and managing a CRM
• Comfortable in a small, fast-moving company where you both sell and lead
• Excellent spoken and written English
• Strong references from previous managers and team members

Important

This is a B2B software sales role. Experience selling consumer products or services (for example automotive, retail, real estate, insurance, mortgages, or telecom plans) does not qualify.

Compensation

Base: CAD $110,000 - $140,000 per year plus commission. On-target earnings (OTE): CAD $170,000 - $220,000 per year (commensurate with experience).

Application Process

• Reply with your resume (PDF or Word) to jobs.2026 (at) jollytech.com with subject “JOL-STM-ON-101326”
• Include your desired base and OTE
• Describe a sales team you led in a few sentences: team size and roles, team quota, attainment, and the most important change you made that improved results. Applications without this information will not be considered.