Head of Sales (PlayerCoach, B2B Infrastructure Sales)

Server Mania; Toronto; Hybrid; CAD 150,000 - 200,000; Full time

Job summary

A leading technology company in Ontario is looking for a Head of Sales who will be responsible for driving revenue growth while leading a high-performance team. The ideal candidate should have at least 5 years of experience in B2B technology sales, a consultative selling approach, and strong leadership skills. This position offers a competitive salary plus uncapped commissions, a hybrid work model, and comprehensive benefits, including health coverage from day one.

Benefits

Comprehensive Health Benefits

Flexible Hybrid Work Model

Competitive Total Compensation

Professional Growth Budget

Qualifications

• 5+ years of experience in B2B technology or infrastructure sales.
• Demonstrated track record in closing and expanding revenue.
• Excellent communication skills for engaging with various stakeholders.

Responsibilities

• Lead and close high-value opportunities through the sales cycle.
• Develop and execute sales plans and quotas.
• Build and manage a high-performing sales team.

Skills

B2B technology sales

Consultative selling

Lead generation

Negotiation skills

Pipeline management

Analytical skills

Education

Bachelor's degree in Sales or Business Administration

Tools

LinkedIn Sales Navigator

CRM platforms

Job description

Job Description

Salary:
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

Role Overview

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 realtime 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.

Core Accountability

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.

Key Responsibilities

Sales Revenue Strategy Execution, Quotas & Forecasting

• 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.

Hands‑On Sales Execution & Deal Leadership

• 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.

Team Leadership, Hiring & Performance Management

• 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.

Process, Reporting & Operational Ownership

• 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 RevOps/operations (if applicable) on tooling, metrics, and dashboards that support accurate and timely decision‑making.

Market Intelligence, Product & Pricing Feedback

• 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.

Strategic Account & Relationship Development

• 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 on expansion, upsell, and cross‑sell opportunities.
• Represent the company at key customer meetings, virtual sessions, and relevant industry events or visits as needed (including occasional travel).

Operational Problem Solving & Continuous Improvement

• Quickly diagnose sales execution issues, pipeline bottlenecks, and customer friction points, and implement corrective actions.
• Continuously refine messaging, positioning, and sales tactics based on win/loss insights and feedback from the field.
• Promote a culture of experimentation, learning, and continuous improvement within the sales team.

Qualifications

• 5+ years of progressively responsible experience in B2B technology or infrastructure sales (e.g., dedicated servers, networking, data centers), including at least 2+ years in a leadership, player‑coach, or senior sales role.
• Proven track record of prospecting, closing, and expanding revenue in a consultative, complex‑solution environment.
• Strong technical understanding of infrastructure solutions with the ability to translate technical capabilities into business value for non‑technical and technical stakeholders.
• Demonstrated hunter mentality with advanced capability in:
  • Lead generation and outbound prospecting
  • Cold outreach and multichannel follow‑up
  • Objection handling and competitive positioning
  • Negotiation and closing complex deals
• Excellent written and verbal communication skills; comfortable engaging with:
  • Business owners and executive stakeholders
  • CTOs and technical decision‑makers
  • Procurement and finance when needed
• Proficiency with:
  • LinkedIn Sales Navigator or similar prospecting tools
  • Modern CRM platforms
  • Outbound sales and pipeline management tools
• Customer‑centric mindset with a focus on long‑term value, retention, and expansion rather than purely transactional wins.
• Strong analytical skills to set, track, and optimize KPIs, ROI, and conversion performance at both individual and team levels.
• Demonstrated ability to lead, coach, and motivate a high‑performance team through accountability, training, and clear expectations.
• Bachelor’s degree in Sales, Business Administration, Marketing, or a related field is preferred; equivalent, demonstrable real‑world performance is strongly considered.
• Ability and willingness to attend in‑person sessions at the Stoney Creek office for leadership, team collaboration, key meetings, and training, with flexibility to accommodate strong candidates who need some balance between in‑office and remote work.

What You’ll Get

• Comprehensive Health Benefits: Full medical and dental coverage from day one
• Hybrid Work Model: Flexible in‑office/remote balance (in‑person collaboration expected for leadership, training, and key meetings)
• Competitive Total Compensation: Base + uncapped commission + performance bonus tied to personal + team results
• PTO & Holidays: Recharge when you need it (with approval)
• Professional Growth: Dedicated budget for sales training, certifications, and industry events
• Modern Tech Stack: Best‑in‑class tools (CRM, LinkedIn Navigator, pipeline mgmt)
• Career Ownership: Player‑coach path to scale with the sales organization

Disclaimer

This job description summarizes the typical functions of the position and is not an exhaustive list of all job responsibilities, tasks, or duties. Responsibilities may evolve over time, and additional relevant duties may be assigned as needed to support organizational goals.