Leader, Sales & Sales Strategy

The Opportunity

This is a high-visibility executive growth role created to transform a large commercial sales organization from a historically reactive, service-focused model into a proactive, outbound market-penetration engine. Reporting directly to executive leadership, this individual will own inside sales execution across Canada while collaborating on broader North American commercial initiatives. You will act as the primary architect of sales execution, owning the strategic roadmap, outbound playbooks, and leadership development across a multi-tiered sales organization. This executive position carries direct operational impact and a clear trajectory into expanded regional leadership responsibilities.

About the Company

The organization is a leading enterprise technology provider connecting top-tier global IT vendors with thousands of commercial partners, resellers, and solution providers across North America. The firm thrives on a collaborative, employee-centric culture that combines deep industry expertise with agile execution to deliver market-leading commercial solutions.

Location

Greater Toronto Area (Ontario). The role operates under a hybrid schedule, requiring approximately 1 2 days per week onsite initially, with a planned progression toward 3 days per week to support team integration and culture building. Regional travel is expected up to 30% of the time to engage with key commercial partners, attend vendor events, and visit regional operating locations.

What You Will Do

Serve as the executive leader responsible for overall operational execution, sales strategy, and revenue performance across the Canadian inside sales organization. Drive revenue growth, profit margin enhancement, account acquisition, and market share expansion across SMB, Mid-Market, and Enterprise segments. Transition the sales force from reactive order execution to a proactive, outbound sales model utilizing structured playbooks, win-back campaigns, and targeted customer acquisition strategies. Serve as a core sales coach, actively developing managers and team members through regular pipeline reviews, live call coaching, and structured talent frameworks. Establish and optimize high-volume inside sales operational metrics, resource allocation models, electronic order integrations, and customer service workflows. Evaluate and implement modern digital tools, including AI-driven sales enablement, telephony integrations, CRM analytics, and operational tracking dashboards. Manage cross-functional alignment with IT, vendor management, marketing, field sales, and executive leadership across various business units. Cultivate strong strategic relationships with major technology vendors, coordinating co-funded growth programs, contests, and joint go-to-market strategies.

Who You Are

Demonstrated track record of senior leadership experience in inside sales, sales operations, or commercial sales leadership within B2B technology, IT channel services, Managed Service Providers (MSPs), Telecom, or adjacent complex technology sectors. Proven experience managing sizeable sales organizations (including direct management reports) in high-volume, multi-channel environment models. Expertise in transforming inbound customer support teams into structured, proactive sales organizations. Strong operational acumen surrounding SLAs, workforce deployment, productivity metrics, P&L management, and sales productivity tools. A charismatic, high-energy sales executive who combines operational rigor with strong hands-on coaching. Exceptional communication skills capable of motivating entry-level representatives and seasoned sales veterans alike.

Education & Qualifications

Bachelor s Degree in Business Administration, Marketing, Information Technology, or equivalent professional experience. Post-hire certifications or vendor accreditations in enterprise technology solutions, leadership development, or modern sales methodologies preferred.

Flexibility & Work-Life Integration

Work Structure: Full-time executive leadership position operating on a hybrid schedule. Schedule: Core business hours with flexibility for business events, vendor functions, and team planning. Requires up to 30% travel across regional customer meetings, vendor events, and secondary office locations. Environment: Professional office environment equipped with modern collaboration tools, digital displays, and interactive team workspaces.

Why Join the Team?

This position offers a rare opportunity to spearhead the growth of a highly respected commercial technology organization. Leaders benefit from a comprehensive total rewards structure, executive mentorship, direct access to executive leadership, and continuous professional growth pathways. You will be empowered to build high-performing teams, leverage modern sales technologies, and shape long-term commercial operating strategy.