Note: The job is a remote job and is open to candidates in USA. Wing Assistant is hiring a hands-on Sales Enablement Trainer to improve the performance of its sales team. The role analyzes calls and sales materials, tests and optimizes messaging and outbound cadences, coaches representatives, and creates training programs to accelerate ramp-up and ongoing development.
Responsibilities
- Sit in the calls — live and recorded — and find exactly where deals are being lost
- Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works
- A/B test sales emails, call openers, demo pitches, and tactics like personalized video — keep the winners, kill the losers
- Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message
- Coach reps one-on-one on real calls and build the objection-handling playbook for our market — then drill it until it's reflexive
- Produce a video training series and self-serve modules with assessments, so new reps ramp fast and tenured reps keep sharpening
Skills
- Have personally sold and closed — ideally outbound/high-volume B2B — and can show your numbers
- Write sales copy that converts and can explain why it works
- Are comfortable on camera and can produce clean training videos without a production team
- Can structure an A/B test, read the result honestly, and make the call
- Coach without crushing — you leave reps better and more confident
- Move fast: a diagnosis becomes a usable fix in hours, not weeks
- Know your way around a CRM (Hubspot plus) and a sales sequencing tool
- Experience in virtual staffing, BPO, or managed services
- Pipedrive or CRM automations
- Video editing
- Sequencing tools (Apollo, Outreach, Salesloft, Instantly, Smartlead)
- Prior sales enablement assets (playbooks, battle cards, certification programs)
Benefits
- Remote work
Company Overview