Who you are

- 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

- Transparent understanding of, and practical experience with, consultative sales methodologies (e.g., MEDDIC/MEDPIC, SPIN, Challenger)

- 4-year university degree (Bachelor's)

- Exceptional business communication skills, enabling you to execute executive storytelling, challenge the status quo, and handle complex contracting negotiations

- High learning agility, analytical thinking, and commercial curiosity to quickly grasp the nuances of various corporate industries

- High AI fluency and advanced CRM tracking skills

- Native-level proficiency in English

- Fluency in an additional language

- Background in SaaS, financial technology, or information security sectors

- Familiarity with enterprise M&A; use cases and corporate compliance workflows

What the job involves

- Proactively build and manage a pipeline focused on the acquisition of new strategic enterprise accounts (new logos)

- Conduct solution-based sales engagements, including client meetings, executive presentations, and product demonstrations (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 that quantify the cost of inaction and address customer priorities, pain points, and ROI

- Structure, negotiate, and close complex deals,



guiding corporate clients step-by-step through enterprise procurement, security compliance, and legal processes

- Orchestrate multi-threading strategies to navigate enterprise politics, establishing strong relationships with C-Suite executives and key stakeholders across various verticals

- Keep an accurate track record of personal sales activities in the CRM, including methodical mid- and long-term forecasting

- Provide relevant customer feedback to the product development team and collaborate with Customer Success, Marketing, and Inbound Sales to maximize revenue and customer satisfaction

The application process

- Screening call with the Talent Acquisition Specialist (40 mins)

- Hiring Manager interview & Cold Call Role-Play (60 mins)

- Discovery Role-Play Presentation with the Hiring Manager (60 mins - requires preparation beforehand to build a business case for a target Fortune 500 company)

- Competency-based interview (CBI) (60 mins)

Benefits

- Remote-first flexibility to shape your ideal workday

- Home workplace budget
- Individual IT budget for extra equipment

- Co-working expense coverage

- Wellness budget for sports, yoga, mental, and other health-related activities

- Funding for sports competitions
- Individual Development Plan based on your career interests

- 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

- Generous internal referral program
- Extra budget for meet ups with teammates

📌 Enterprise Account Executive (Toronto)
🏢 iDeals
📍 Toronto