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This is a strategic sales role where you’ll own your business end to end, supporting SMB customers. You’ll work closely with enterprise prospects, dig into their business challenges, and guide them toward solutions that make sense for where they are and where they want to go.
Job Responsibility:
Manage the full sales cycle from prospecting to close for enterprise accounts
Work directly with C-suite and senior leaders to understand their goals and map OnePlan’s solutions to their priorities
Deliver tailored demos and lead technical discovery alongside our Solution Consultants
Build and configure use cases and guide customers through pilots and trial
Create territory plans and account strategies that support a strong, healthy pipeline
Build trusted relationships with prospects, partners, and internal teams
Prepare and negotiate pricing, SOWs, and contract terms
Maintain accurate pipeline and forecasts in Salesforce
Work closely with Customer Success and Product to ensure smooth handoffs and long-term customer value
Identify upsell and cross-sell opportunities within existing accounts
Stay plugged into industry trends, Microsoft ecosystem programs, and competitive movements
Requirements:
Experience selling SaaS or Microsoft ecosystem solutions into large enterprise accounts
Comfort managing long, complex sales cycles with multiple stakeholders
A consultative approach that builds trust and keeps conversations grounded
Confidence engaging C-suite and senior leaders on strategic business outcomes
Familiarity with sales methodologies such as MEDDPICC, Challenger, or Sandler
Experience partnering with Solution Consultants or presales teams to shape deals
Ability to guide customers through pilots, use cases, and early solution validation
Strong ownership mindset with steady communication and follow through
Nice to have:
Experience selling PPM, work management, or planning software
Understanding of Microsoft’s co-sell programs and partner ecosystem
Exposure to global enterprise environments or long-cycle strategic sales
Comfort configuring product scenarios or hands-on demos
What we offer:
Comprehensive health, dental, and vision benefits, with additional insurance options
Employer RRSP and 401K matching programs
A fun, collaborative, and diverse environment with regular health and team challenges
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