Sales Enablement Trainer

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

📋 Description

• Participate in both live and recorded calls to identify precisely where deals are being lost.

• Revise the copy, scripts, and sequences that are underperforming, and validate the effectiveness of the new versions.

• Conduct A/B tests on sales emails, call introductions, demo presentations, and techniques such as personalized video — retain the successful strategies and eliminate the ineffective ones.

• Develop and optimize outbound cadences to ensure representatives follow up at the appropriate time, through the right channel, and with the correct message.

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

• Create a video training series and self-service modules with assessments, enabling new representatives to ramp up quickly while allowing experienced representatives to continuously improve.

⛳️ Requirements

• Have personally engaged in selling and closing deals — preferably in an outbound/high-volume B2B context — and be able to present your results.

• Craft sales copy that drives conversions and articulate the reasoning behind its effectiveness.

• Be at ease on camera and capable of producing polished training videos independently, without the need for a production team.

• Design and implement A/B tests, interpret the results objectively, and make informed decisions.

• Provide coaching in a constructive manner — enhancing representatives' skills and boosting their confidence.

• Act swiftly: transform a diagnosis into a practical solution within hours, not weeks.

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

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

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Flexible work hours and the option for remote work.

• Opportunities for professional development and continuous learning.

• Collaborative and supportive work environment.