Enterprise Account Executive – Toronto

Idealsvdr; Toronto; Hybrid; CAD 110,000 - 165,000; Full time

Benefits offered by this job

Remote-first flexibility

Home office budget

Co-working expense coverage

Competitive base + commission

Job summary

Ideals is seeking an Enterprise Account Executive to drive new logos and expand existing enterprise relationships in the North American market, with a focus on Toronto, Ontario. You will guide multi-month sales cycles, articulate a compelling ROI, and navigate procurement, security, and legal steps with C-suite stakeholders.

As a quota-carrying seller, you will balance base salary with performance-based variable compensation, working within a remote-friendly, high-support environment that values

Qualifications

• 4–7 years of quota-carrying B2B sales experience, including 2+ years in Enterprise sales.
• Proven ability to manage lengthy enterprise sales cycles and close complex deals.
• Experience selling to C-suite executives and multi-threading within large organizations.
• Familiarity with MEDDIC/MEDPIC, SPIN, Challenger sales methodologies.

Responsibilities

• Build and manage a pipeline focused on acquiring new enterprise accounts (new logos).
• Lead solution-based engagements: client meetings, executive presentations, product demos (in-person or virtual).
• Maintain White Space analysis and drive upsell/cross-sell within existing customers.
• Develop business cases quantifying ROI and cost of inaction for customers.
• Negotiate and close complex deals through procurement, security, and legal steps.
• Foster cross-functional relationships with C-Suite stakeholders across verticals.
• Keep CRM up-to-date with activities and forecasts, using data to inform strategy.
• Provide customer feedback to product, CS, and marketing to maximize revenue and satisfaction.

Skills

Quota-carrying sales

Enterprise sales experience

Executive communication

Sales cycle management

CRM proficiency

Negotiation

Multi-threading

Market research

Education

Bachelor's degree

Tools

Salesforce (CRM)

Job description

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

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)

Unrivaled recognition

• We’re proud to be celebrated by our customers and teammates
• G2 Market Leader
• Based on 800+ reviews
• 4.7 out of 5
• Trusted by talent
• based on 100+ reviews
• 4.1 out of 5
• Reach global
  with a team celebrated by your sales peers
• You’ll enjoy the right blend of support and autonomy to help you reach your full potential, anywhere in the world
• Remote-first flexibility to shape your ideal workday
• Home workplace budget
• Co-working expense coverage