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Account Executive

Job in Toronto, Ontario, C6A, Canada
Listing for: Ask-AI
Full Time position
Listed on 2026-02-28
Job specializations:
  • Sales
    Business Development, Sales Representative, Sales Development Rep/SDR, B2B Sales
Salary/Wage Range or Industry Benchmark: 80000 - 100000 CAD Yearly CAD 80000.00 100000.00 YEAR
Job Description & How to Apply Below

Overview

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About Ask-AI

Ask-AI is an Enterprise AI platform designed to transform how organizations equip their employees and serve their customers. Ask-AI provides a single platform that allows companies to connect a variety of knowledge sources (Docs, Comms, Tickets, KBs, etc.) and build out an array of use cases using generative AI (Employee Assistant, Customer Self-Service, Voice of Customer, Account Analysis, Knowledge Base, AI Apps, etc.).

By leveraging Ask-AI, enterprise teams are able to set a foundational AI strategy that satisfies use cases across multiple departments, avoids tool sprawl, and helps consolidate their tech stack. Ask-AI is a Series A company with traction and growth. It has offices in Toronto and Tel Aviv. The company is led by a team of NLP PhDs and Professors and was founded by Alon Talmor, PhD in AI/NLP and former Chief Data Scientist at Salesforce.

About The Role

We’re looking for a Senior Account Executive to join our sales organization. This is an opportunity to play a pivotal role in helping us achieve our next phase of growth and to build out a world-class sales culture. In this role, you will be responsible for driving new business by taking a consultative approach with prospects to understand their business and identify use cases that can be solved by the Ask-AI platform.

You will work with internal teams to navigate complex org structures and drive a value-driven sales experience. This role is ideal for someone who is motivated to make their mark and to learn and sell a variety of use cases and value propositions.

Areas of Focus
  • Lead full cycle sales process from lead to close in our Enterprise Segment (1K+ employees)
  • Navigate complex organizational structures and build relationships with executive sponsors and champions
  • Understand customer business objectives and deliver a value-driven sales cycle that resonates with their needs
  • Create ROI and business justification reports using a data-driven approach
  • Run tight proof-of-concepts (POCs) based on business success criteria
  • Work closely with leadership to identify product gaps and opportunities
  • Work closely with the marketing organization to improve messaging and positioning based on what resonates with your cycles
  • Help mentor SDRs and guide their career development
Requirements
  • 3+ years of closing experience in sales, with a proven track record of being a top performer
  • Experience selling in a startup environment with a track record of success
  • Proven success in closing complex deals and navigating multi-stakeholder environments
  • Ability to learn, pitch, and demonstrate highly technical products in a fast-paced, growth-driven environment
  • Experience selling into Support or IT personas
  • Strong understanding of Command of the Message and MEDDPIC sales methodologies
Seniority level
  • Mid-Senior level
Employment type
  • Full-time
Job function
  • Sales and Business Development
Industries
  • Technology, Information and Internet

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