Enterprise Account Executive - Toronto

Ideals is a global B2B SaaS product company recognized as the most highly rated and customer-centric brand in the secure business collaboration market. Trusted by over 2,000,000 users from 300,000 companies globally, we help people run high-stakes processes and make important decisions with less stress, higher quality, and shorter hours.

Ideals Virtual Data Room (VDR): Secure document sharing and collaboration for due diligence, fundraising, corporate reporting, licensing, clinical trials, and other complex transactions.

To support Ideals' rapid growth in North America, we are looking for our first Enterprise Account Executive (Business Development Manager) to focus on our Corporate segment in Toronto, Ontario, Canada. You’ll join a team of 20+ Key Accounts teammates in the US and Canada. Unlike our advisory-focused motions, you will sell directly to a wide variety of enterprise corporations across diverse industries (such as energy, pharma, biotech, and telecommunications).

As a quota-carrying strategic seller, you will grow revenue, acquiring new enterprise accounts and expanding existing ones. You will act as an impactful industry expert, generating demand, navigating complex 6- to 9-month sales cycles, and often displacing incumbent vendors through deep discovery and consultative selling.

Compensation package: 50% base salary; 50% performance-based variable.

Estimated Salary range for this role: $90,000-$110,000 CAD

Estimated OTE: $180,000-$220,000 CAD

This role requires residency in the Toronto, Ontario region.

• High trust from sales peers: Ideals ranks among the top companies on RepVue, as rated by sales professionals. Great Place To Work® Certified in the US and the UK (2026). Expect strong Sales Enablement, RevOps, Marketing support, and a structured onboarding ramp.

• Market-leading position: Be part of an established org with 18+ years in the VDR business, powering 10%+ of global M&A activity, with a 31% CAGR against competitors' 11%.

• Real growth trajectory: Join a profitable bootstrapped SaaS targeting 5x revenue growth and unicorn status in the next five years.

• 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

• 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 (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

• 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)

We highly value our people, so we will empower you with all the resources and support to help you reach your full potential.

• 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

• Private Health Insurance via Manulife for the employee and dependents

• Virtual Health Insurance via Dialogue

• Registered Retirement Savings Plan (RRSP) for the employee via Wealthsimple

• Funding for sports competitions

• 15 business days of annual leave

• Paid health-related time off

• Budget for meetups with your local team

• Generous internal referral program

Commitment, Excellence, Collaboration, Trust and Care are core values to the Ideals team. For us, these are the principles that every Idealer lives and breathes. We are on the lookout for like-minded individuals who share our values. By doing so, we create a team where talents feel at ease and work to the best of their abilities.

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Ideals is an equal opportunity employer

At Ideals, we value a diverse, inclusive workforce and we provide equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individual’s race, color, sex, gender identity, gender expression, religion, age, national origin or ancestry, citizenship, physical disability, medical condition, family care status, marital status, domestic partner status, sexual orientation, genetic information, military or veteran status, or any other basis protected by federal, state or local laws. If you need assistance or an accommodation due to a disability, you may inform us in the 'Additional information' field when submitting your application.