Enterprise Account Executive selling Ideals’ secure virtual data rooms to Toronto corporations. Building enterprise pipeline, closing complex deals, and expanding strategic accounts.
Responsibilities
Proactively build and manage a pipeline focused on acquiring new strategic enterprise accounts (new logos)
Conduct solution-based sales engagements, including client meetings, executive presentations, and product demonstrations, both face-to-face and virtual
Maintain “White Space” analysis and execute strategic initiatives to upsell and cross-sell within the existing customer base
Develop and deliver comprehensive business cases quantifying the cost of inaction and addressing customer priorities, pain points, and ROI
Structure, negotiate, and close complex deals through enterprise procurement, security compliance, and legal processes
Orchestrate multi-threading strategies and establish relationships with C-Suite executives and key stakeholders across various verticals
Track personal sales activities accurately in the CRM, including methodical mid- and long-term forecasting
Provide customer feedback to the product development team
Collaborate with Customer Success, Marketing, and Inbound Sales to maximize revenue and customer satisfaction
Participate in screening, hiring manager, cold-call role-play, discovery role-play presentation, and competency-based interview stages
Requirements
4–7 years of demonstrable quota-carrying success in B2B sales, including 2+ years of Enterprise sales experience
Proven track record of managing lengthy or complex enterprise sales cycles
Significant experience selling directly to C-level executives (CxOs) and multi-threading within large enterprise organizations
Clear understanding of and practical experience with consultative sales methodologies, such as MEDDIC/MEDPIC, SPIN, or Challenger
4-year university degree (Bachelor's)
Exceptional business communication skills, including executive storytelling and complex contracting negotiations
High learning agility, analytical thinking, and commercial curiosity
High AI fluency and advanced CRM tracking skills
Native-level proficiency in English
Fluency in an additional language is nice to have
Background in SaaS, financial technology, or information security sectors is nice to have
Familiarity with enterprise M&A use cases and corporate compliance workflows is nice to have
Residency in the Toronto, Ontario region
Legal authorization to work in Canada
Benefits
Remote-first flexibility to shape your ideal workday
Home workplace budget
Co-working expense coverage
Individual IT budget for extra equipment
Top-tier tech and AI-powered tools
Access to Ideals Academy with numerous courses
Investment in external learning and development activities
Guidance in Personal Development Plan creation
Professional literature and subscriptions coverage
Support of your passion as a speaker or writer
Internal talent mobility opportunities
100% employer-paid health insurance for US employees with a 401(k) match program
Mental health activities reimbursement
Funding for sports competitions
20 business days of annual leave
Paid health-related time off
Budget for meetups with your local team
Generous internal referral program
Performance-based variable compensation (50% of compensation package)
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