Account Executive

Ask-AI; Toronto; On-site; CAD 70,000 - 90,000; Full time

Job summary

A growing AI technology company in Toronto is looking for a Senior Account Executive to drive new business through a consultative approach. The ideal candidate will have over 3 years of sales closing experience and a track record of success in startup environments. Responsibilities include managing the full sales cycle, understanding customer needs, and collaborating with internal teams. This is a great opportunity to make a significant impact in a fast-paced growth environment.

Qualifications

• 3+ years of sales closing experience with a proven top-performer track record.
• Experience selling in startup environments with successful outcomes.
• Proven success in closing complex deals and managing multi-stakeholder environments.

Responsibilities

• Drive new business through a consultative approach.
• Lead full-cycle sales process from lead generation to closing.
• Create ROI and business justification reports using data-driven methods.

Skills

Sales closing experience

Consultative sales approach

Ability to navigate complex organizational structures

Data-driven decision making

Mentorship skills

Job description

Job Description

About Ask-AI :

Ask-AI is an Enterprise AI platform designed to transform how organizations equip their employees and serve their customers. It provides a single platform that connects various knowledge sources (Docs, Comms, Tickets, KBs, etc.) and enables a range 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 can set a foundational AI strategy that spans multiple departments, avoids tool sprawl, and consolidates their tech stack.

Ask-AI, a Series A company, has experienced significant growth—tripling year over year, with a 97% GRR, and a 75% WAU : MAU ratio (similar to Slack).

Founded by Alon Talmor, PhD in AI / NLP and former Chief Data Scientist at Salesforce, the company is supported by leading NLP PhDs and Professors, with offices in Toronto and Tel Aviv, positioning it for continued growth.

About the Role

We’re seeking a Senior Account Executive to join our sales team.

This role offers the opportunity to contribute to our growth and build a world-class sales culture.

You will be responsible for driving new business through a consultative approach, understanding clients' businesses deeply, and identifying use cases that can be addressed by the Ask-AI platform.

You will collaborate with internal teams to navigate complex organizational structures and deliver a value-driven sales experience.

This role is ideal for someone who is -

• Looking to make a significant impact on a growing company.
• Motivated to learn and sell diverse use cases and value propositions.
• Experienced in delivering excellent software buying experiences.

Areas of Focus

1. Lead full-cycle sales process from lead generation to closing in the Enterprise Segment (1K+ employees).
2. Navigate complex organizational structures and build relationships with executive sponsors and champions.
3. Understand customer objectives and deliver a sales process that aligns with their needs.
4. Create ROI and business justification reports using data-driven methods.
5. Manage proof-of-concepts (POCs) based on business success criteria.
6. Collaborate with leadership to identify product gaps and opportunities.
7. Work with marketing to refine messaging and positioning based on market feedback.
8. Mentor SDRs and support their career development.

Requirements :

• 3+ years of sales closing experience with a proven top-performer track record.
• Experience selling in startup environments with successful outcomes.
• Proven success in closing complex deals and managing multi-stakeholder environments.
• Ability to learn, pitch, and demonstrate highly technical products in a fast-paced, growth environment.
• Experience selling to Support or IT personas.
• Strong understanding of Command of the Message and MEDDPIC sales methodologies.