Head of Sales; Player‑Coach, B2B Infrastructure Sales

Location:

GTA, Canada
Full-Time Employment
Hybrid (Flexible In-Office Schedule)
Senior Manager/Supervisor Level
OTE Range: $150,000 – $200,000+ CAD (performance-based) Uncapped commissions

The Head of Sales is a hands‑on, revenue‑driving leader who sells alongside the team while building and scaling a high‑performance B2B infrastructure sales function. This role combines individual deal ownership with leadership of the sales team, operating within the overall revenue strategy set by the Chief Revenue Officer.

You will personally close high‑value opportunities, lead the sales team to consistent quota attainment, and act as the real‑time voice of the market to the CRO and leadership. The ideal candidate is a true player‑coach with a hunter mentality, comfortable owning both personal outcomes and team performance in a technical, infrastructure‑focused environment.

The Head of Sales is fully accountable for:

• Personal revenue production (defined subset of key opportunities)
• Team revenue performance and quota attainment
• Pipeline integrity and forecast accuracy
• Market intelligence and pricing feedback to leadership
• Strategic account development and expansion within the sales organization

Success in this role requires autonomy, ownership, resilience, and disciplined execution.

• Develop and execute sales plans, quotas, and revenue targets for the sales team aligned with the company’s revenue strategy defined by the CRO.
• Own quarterly and annual sales forecasts for your organization with clear accountability for accuracy and delivery.
• Translate company and marketing objectives into concrete sales action plans, cadences, and activities.
• Monitor sales KPIs, conversion metrics, and pipeline velocity to ensure consistent target achievement and predictable execution.

• Personally lead and close a defined subset of high‑value opportunities through the full sales cycle using consultative, solution‑oriented selling.
• Maintain an active personal pipeline, operating with a hunter mentality across inbound and outbound channels.
• Provide deal strategy support, coaching, and live assistance to reps on complex or strategic opportunities.
• Ensure efficient pipeline management, CRM discipline, and clean handoff to Account Management or Customer Success upon close.

• Identify sales hiring needs in collaboration with the CRO and People/HR; participate in recruiting, selection, and onboarding of sales talent.
• Build, develop, and retain a high‑performing sales team through coaching, mentoring, and structured performance management.
• Set and enforce clear expectations around activity, quality, pipeline hygiene, and results.
• Run regular 1:1s, pipeline reviews, and performance check‑ins focused on skill development and accountability.

• Own sales process design and continuous improvement for your team (stages, qualification criteria, cadences, and best practices).
• Serve as the primary point of contact for sales performance reporting (excluding finance), including pipeline status, forecast, and risk.
• Prepare clear, structured updates for leadership on pipeline health, forecast changes, and execution risks, along with recommended actions.
• Partner with Rev Ops/operations (if applicable) on tooling, metrics, and dashboards that support accurate and timely decision‑making.

• Act as the voice of the customer and the market for the sales organization, sharing insights with the CRO and relevant teams.
• Provide structured feedback on pricing, packaging, service gaps, and competitor positioning to inform revenue strategy and product direction.
• Identify emerging customer needs, buying patterns, and market shifts, flagging risks and opportunities early with proposed solutions.

• Build and deepen long‑term relationships with strategic accounts through executive‑level engagement and regular business reviews.
• Partner with internal teams to uncover and execute…