Technical Sales Specialist

This is a fully remote position, open to applicants in Canada.

📋 Description

• Reduce the ramp-up time for representatives by managing the technical aspect of sales onboarding and continuous training, enabling them to independently handle most technical discussions without routing through TSS;

• Remove the risk of a single point of failure in technical expertise by alleviating the existing TSS workload across pre-sales, expansion, and partner-led transactions, ensuring no deal is delayed due to reliance on one individual;

• Accelerate deal cycles by providing demonstrations that set the internal benchmark — the type that representatives study, replicate, and learn from;

• Propel deals to closure as a technical co-closer, rather than just a validator — emphasizing value, addressing gaps with future plans and vision, and maintaining momentum even when the response isn't a straightforward "yes, today";

• Influence the product roadmap by converting field trends into actionable feedback that product managers can utilize — and ensuring representatives are informed when new features are released;

• Boost Migrate-to-Protect attachment rates by assisting in expansion discussions with current clients and facilitating connections between products for AEs and AMs;

• Enhance the team's technical capabilities by creating reusable resources and AI-driven workflows, ensuring that repetitive issues do not burden the team repeatedly.

⛳️ Requirements

• Proven experience in a customer-facing technical sales position within a B2B SaaS environment;

• Knowledge of the Microsoft 365 platform (experience in governance, migration, or related fields is highly advantageous);

• Strong business acumen demonstrated by a successful history of influencing deals to closure;

• Exceptional demo skills — treating it as a craft rather than merely a task;

• A proactive builder mentality: seeking systems and AI workflows that enhance your expertise instead of trading your time for every challenge;

• Genuine fluency in AI — comfortable creating your own workflows rather than just using tools superficially;

• Effective and confident communicator across various audiences, from IT administrators to CIOs to partner sales representatives (bilingual in French and English is a significant advantage).

🏝️ Benefits

• Health insurance

• Commission eligible

• Professional development opportunities