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 emails, calls, and sales cadences used by its sales team. The role focuses on analyzing calls, optimizing sales messaging, coaching representatives, conducting A/B tests, building outbound cadences, and creating training content to accelerate ramp-up and improve performance.
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 arrangement
- Room to grow as the program proves it drives revenue
Company Overview