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Digital Sales Specialist; DSS - Technology Sales

Job in Markham, Ontario, I3P, Canada
Listing for: Leadingtalent
Full Time position
Listed on 2026-06-20
Job specializations:
  • Sales
    Sales Development Rep/SDR, Technical Sales, Sales Engineer, Sales Representative
Salary/Wage Range or Industry Benchmark: 60000 - 80000 CAD Yearly CAD 60000.00 80000.00 YEAR
Job Description & How to Apply Below
Position: Digital Sales Specialist (DSS) - Technology Sales

Introduction

Join IBM Canada’s fast-paced Digital Sales team where you’ll drive high-volume pipeline growth, engage customers through digital channels, and close deals  a Digital Sales Specialist (DSS) you will partner with your Digital Technical Specialist, Marketing, Business Partners to present compelling value propositions, design PoCs, and support upsell/cross-sell efforts with customers. Digital Sales Specialists operate well in ambiguity, are self‑starters, and find solutions to unique customer problems.

Digital Sales Specialists (DSS) are accountable for both Existing and New Client Acquisition, using a mix of telephone, email, social and event activities to meet and engage with customers and prospects. Upon completion of IBM Global Sales School, Digital Sales Specialists are aligned to a unique territory to make their own.

Part of IBM’s onboarding process, new hires are placed in IBM’s Global Sales Program, a structured, extensive set of training activities geared toward building elite digital sales capabilities. The first six weeks focus on IBM’s sales methodology, consultative sales, and real‑world application via ongoing mentorship and monthly milestones.

Digital Sales Specialists operate in a hybrid environment (three days in office per week) at our flagship Head Office in Markham, Ontario.

Your role and responsibilities

As a Digital Sales Specialist, you will become a trusted advisor for IBM customers and prospects, engaging with IBM technical and ecosystem partners. You will collaborate on client engagements during the critical early phases of the sales cycle, guiding prospects to our award‑winning technology solutions. Your success in this role will contribute to the prosperity of your career, team and clients.

Your primary responsibilities include:

  • Account Planning and Stakeholder Management
    • Proactively reach out to clients using Digital Tools (telephone, email, social media) to engage with prospects and existing customers to identify new opportunities (up‑sell/cross‑sell or new customer)
    • Engage in planning with colleagues (Digital Technical Specialist and Sales Development Representatives) on tactical territory plans regularly
    • Meet weekly KPIs for outbound activities (100+ calls per week, 200 activities (emails/Linked In), opportunity identification, progression and achieving quarterly targets – key tenet for role)
  • Sales Execution
    • Become an expert in a focused set of products, depending on the team you will be part of (eg. Automation, Data&AI, Storage, Power/Cloud), understanding applicable use‑cases, customer probes, and key value prop & differentiators
    • Own opportunity identification and solution development for revenue generation
    • Engage the appropriate technical resources to secure technical sales wins
    • Partner with clients to co‑create solutions using assigned offerings/products
    • Utilize tool stack and social selling skills effectively
  • Managing for Growth
    • Maintain up‑to‑date technical proficiency and product knowledge
    • Participate in Proof of Concepts and Proof of Technology to process opportunities
    • Manage territory and strategy, and A/B test different outreach tactics and collaborate with peers on best‑of‑breed outcomes
    • Present quarterly business reviews to refine outreach and benefit in coaching
  • Required education

    Bachelor’s Degree

    Preferred education

    Bachelor’s Degree

    Required technical and professional expertise
    • Outcome based: Track record of delivering outcomes on committed timelines, experience in ‘working backwards’ from a problem statement and all the steps to achieve the desired outcome
    • Teaming: Ability to work with cross‑functional teams in and outside of IBM to support customer objectives and achieve results; coachability and communication are key
    • Time Management: Able to prospect, engage with your territory and customers (100+ calls a week), while also supporting progression week to week (PoCs/demos, presentations, briefings) to drive quarterly targets
    • Self‑Starter: Willingness to work in ambiguity (limited structure), with coaching/mentors available, to develop territory and engagement plan with customers
    • Ability to influence client technology decisions points (Why IBM…)
    • Track record of…
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