Director of Inside Sales, Montreal, Canada – Visa Sponsorship Available

Visa type confirmed: Immigration Support Possible

About the Role

We are seeking a Director of Inside Sales to guide our PLG team (transactional subs) to articulate the transformative impact of our AI autonomous agents to prospective SMB and mid-market clients. This multifaceted role combines technical expertise, visionary insight, strategic collaboration, and a commitment to driving value through solution selling. As part of our rapidly growing platform and its tens of thousands of sign-ups, we invite entrepreneurial spirits who can coach and mentor a growing ISR team from inception to close. This position will help shape our sales motions for years to come. The role is in-office and reports to the CRO. Our client is open to sponsoring visas for U.S. and Mexican nationals to join us in Canada.

About Us

We empower organizations by integrating autonomous agents into their core business functions. Our dedicated team of top-tier developers, engineers, and business strategists is driving our Platform-as-a-Service (PaaS) to become the standard solution for multi-agent systems, serving enterprises, governments, and educational institutions of various scales.

Responsibilities

Leadership & Team Management

• Recruit, onboard, and mentor a high-performing team of Inside Sales Representatives (ISRs) focused on PLG transactional sales.
• Set clear KPIs and hold the team accountable for performance and pipeline growth from MQL to close.
• Foster a high-performance culture of curiosity, collaboration, and continuous improvement.

Sales Execution & Coaching

• Lead daily/weekly sales standups and pipeline reviews to drive velocity and predictability.
• Shadow calls and provide real-time feedback and structured coaching to elevate solution-selling capabilities.
• Empower ISRs to articulate the business value of autonomous AI agents to SMB and mid-market buyers.

Strategy & Process Optimization

• Design, document, and continuously refine sales playbooks, cadences, and talk tracks.
• Collaborate with Growth, Product, and Marketing teams to align inbound motions with sales strategies.
• Use data-driven insights to improve conversion rates across the sales funnel.

Cross-Functional Collaboration

• Partner with the CRO and RevOps to ensure accurate forecasting, quota-setting, and reporting.
• Provide field insights to Product and Marketing to inform roadmap and campaign priorities.
• Participate in GTM experimentation and support new play launches (e.g., vertical focus, product-led upgrades).

CRM and Tools Hygiene

• Ensure consistent use of CRM (e.g., HubSpot) and sales engagement tools.
• Monitor and improve SDR/ISR workflows, ensuring accurate tracking of activities and outcomes.

Requirements

Experience

• 3–5+ years of experience in inside sales or sales development roles, with at least 2 years in a leadership capacity.
• Proven success selling SaaS or PaaS solutions, ideally to SMBs and mid-market segments.
• Familiarity with product-led growth motions and high-velocity transactional sales.

Skills & Attributes

• Strong coaching acumen with a passion for developing early-career talent.
• Exceptional communication and storytelling skills — ability to convey the impact of AI agents clearly.
• Deep understanding of sales funnel metrics and a data-first approach to pipeline management.
• Highly organized with a bias for action, able to manage multiple priorities in a fast-paced environment.

Technical Fluency

• Comfort working with LLM-powered products or technical buyers is a strong plus.

• Familiarity with sales tools such as Salesforce, HubSpot, Outreach, or Gong.

Culture & Fit

• Entrepreneurial mindset — thrives in a fast-growth, startup environment.
• Willingness to work on-site at our Canadian HQ (visa sponsorship available for U.S. and Mexican nationals).
• Committed to our mission to transform customer and business interactions through autonomous AI agents.

Benefits

• Contributing to the growth of the most popular AI agent platform in the world.
• Top-tier health benefits and access to telemedicine for you and your family.
• 4 weeks of vacation.
• Modern office in the heart of downtown Montreal.
• A forward-thinking and inclusive workplace.
• Rich opportunities for career development.

Join us in our mission to streamline business processes with AI, where your contributions will shape the future of autonomous agents!

Register Your Interest In A New Life In Canada

If this role isn’t quite what you are looking for but a Sponsored job in Canada is still of interest. Click here to upload your resume and register your interest with our Canadian Recruitment Partners

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