Sales Enablement Trainer

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

📋 Description

• Participate in both live and recorded calls to pinpoint where deals are falling through.

• Revise any non-converting copy, scripts, and sequences, demonstrating the effectiveness of the new versions.

• Conduct A/B tests on sales emails, call openers, demo pitches, and strategies such as personalized video — retain successful approaches and discard ineffective ones.

• Develop and refine outbound cadences to ensure representatives follow up at the optimal time, via the appropriate channel, with the correct message.

• Provide one-on-one coaching for representatives during actual calls and create an objection-handling playbook tailored to our market — practice until it becomes second nature.

• Create a video training series and self-service modules complete with assessments to accelerate the ramp-up for new representatives while enabling experienced reps to continuously improve.

⛳️ Requirements

• Have a proven track record of personal sales and closures—preferably in outbound/high-volume B2B—and be able to present your metrics.

• Craft sales copy that effectively converts and articulate the reasons behind its success.

• Feel at ease on camera and capable of producing high-quality training videos independently.

• Be able to design an A/B test, interpret the results accurately, and make informed decisions based on those results.

• Provide constructive coaching that enhances representatives' skills and confidence.

• Act quickly: transform diagnoses into actionable solutions within hours, not weeks.

• Be proficient with a CRM (preferably Hubspot) and a sales sequencing tool.

• Preferred: Experience in virtual staffing, BPO, or managed services; familiarity with Pipedrive or CRM automations; skills in video editing; knowledge of sequencing tools (such as Apollo, Outreach, Salesloft, Instantly, Smartlead); and prior experience with sales enablement materials (including playbooks, battle cards, and certification programs).

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Opportunities for professional development and continuous learning.

• Flexible work environment with remote options.

• Comprehensive health and wellness benefits.

• Collaborative team culture that values innovation and creativity.