ServerMania

Head of Sales – Player-Coach, B2B Infrastructure Sales

ServerMania

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

Visit company website

Explore more

✨ AI Apply
Apply

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