ServerMania

Head of Sales – Player-Coach, B2B Infrastructure Sales

ServerMania

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

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Salary

💰 CA$150,000 - CA$200,000 per year

Job Level

Lead

About the role

  • 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.
  • Personally close high-value opportunities and lead the sales team to consistent quota attainment.
  • Develop and execute sales plans, quotas, and revenue targets aligned with the company's revenue strategy defined by the CRO.
  • Monitor sales KPIs, conversion metrics, and pipeline velocity to ensure consistent target achievement.
  • Personally lead and close a defined subset of high-value opportunities through the full sales cycle.
  • Identify sales hiring needs, participate in recruiting, selection, and onboarding of sales talent.
  • Set and enforce clear expectations around activity, quality, pipeline hygiene, and results.
  • Serve as the primary point of contact for sales performance reporting, including pipeline status, forecast, and risk.
  • Act as the voice of the customer and market for the sales organization, sharing insights with the CRO and relevant teams.
  • Build and deepen long-term relationships with strategic accounts through executive-level engagement and regular business reviews.

Requirements

  • 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 multi-channel 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.
Benefits
  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
B2B salesinfrastructure saleslead generationoutbound prospectingnegotiationclosing complex dealssales planningKPI trackingpipeline managementconsultative selling
Soft Skills
leadershipcoachingcommunicationrelationship buildinganalytical skillscustomer-centric mindsetaccountabilityteam motivationobjection handlingexecutive engagement