Enterprise Account Executive - Toronto

Ideals; Toronto; On-site; CAD 120,000 - 160,000; Full time

Benefits offered by this job

Remote-first

Home office budget

Co-working coverage

AI-enabled tools

AI tools access

Ideals Academy

RRSP eligibility

Health insurance

Paid time off

Team meetups

Job summary

Ideals is seeking an Enterprise Account Executive to lead new logo acquisitions and expand strategic enterprise relationships across diverse industries from Toronto, Ontario, Canada. You will engage C-level executives, run multi-month sales cycles, and drive revenue with a balanced base and performance-based compensation.

The role requires residency in the Toronto region, a 4-year degree, and proven quota-carrying success in B2B and enterprise sales.

Qualifications

• 4–7 years of quota-carrying B2B sales experience, including 2+ years in enterprise sales.
• Proven ability to manage lengthy or complex enterprise sales cycles.
• Experience selling to C-level executives and multi-threading in large orgs.
• Familiarity with MEDDIC/MEDPIC, SPIN, Challenger sales methods.
• Bachelor's degree (4-year university).
• Exceptional business communication and executive storytelling skills.
• High learning agility, analytical thinking and commercial curiosity.
• High AI fluency and strong CRM usage.
• Native-level English proficiency.

Responsibilities

• Build and manage a pipeline focused on acquiring new enterprise accounts (new logos).
• Conduct solution-based sales engagements with meetings, executive presentations, and product demos (in-person/virtual).
• Maintain White Space analysis and upsell/cross-sell within existing customers.
• Develop business cases quantifying ROI and addressing customer priorities.
• Structure, negotiate, and close complex deals through procurement, security, and legal steps.
• Navigate enterprise politics and build relationships with C-Suite and stakeholders across verticals.
• Keep accurate activity records in CRM and forecast mid- and long-term outcomes.
• Provide customer feedback to product, collaborate with Success, Marketing and Inbound Sales.

Skills

Quota-carrying

Enterprise sales

C-level selling

MEDDIC/SPIN

Executive storytelling

CRM proficiency

English fluency

Education

Bachelor's degree

Job description

Get to know us

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.

The role

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.

This role requires residency in the Toronto, Ontario region.

Why Ideals?

• High trust from sales peers: Ideals ranks among the Top 10% of 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.

What you will do

• 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

What you bring

• 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

Nice to have

• 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

Our assessment 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)

What we offer

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

For your best work

• 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

For your growth

• 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

For your well-being

• 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

Extra perks

• Budget for meetups with your local team
• Generous internal referral program

Our culture

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.

Discover more

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.