Head of Sales (PlayerCoach, B2B Infrastructure Sales)

Location: GTA Canada
Full-Time Employment

Hybrid (Flexible In-Office Schedule)

Senior Manager/Supervisor Level

OTE Range: $150000 $200000 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 highperformance 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 highvalue 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 playercoach with a hunter mentality comfortable owning both personal outcomes and team performance in a technical infrastructurefocused 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 companys 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 highvalue opportunities through the full sales cycle using consultative solutionoriented 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 highperforming 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 checkins 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 decisionmaking.

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 longterm relationships with strategic accounts through executivelevel engagement and regular business reviews.
• Partner with internal teams to uncover and execute on expansion upsell and crosssell 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 playercoach or senior sales role.
• Proven track record of prospecting closing and expanding revenue in a consultative complexsolution environment.
• Strong technical understanding of infrastructure solutions with the ability to translate technical capabilities into business value for nontechnical and technical stakeholders.
• Demonstrated hunter mentality with advanced capability in:
  • Lead generation and outbound prospecting
  • Cold outreach and multichannel followup
  • 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 decisionmakers
  • Procurement and finance when needed
• Proficiency with:
  • LinkedIn Sales Navigator or similar prospecting tools
  • Modern CRM platforms
  • Outbound sales and pipeline management tools
• Customercentric mindset with a focus on longterm 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 highperformance team through accountability training and clear expectations.
• Bachelors degree in Sales Business Administration Marketing or a related field is preferred; equivalent demonstrable realworld performance is strongly considered.
• Ability and willingness to attend inperson 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 inoffice and remote work.

What Youll 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.

Required Experience:

Director