# Sales Enablement Trainer at Wing Assistant

Sales Enablement Trainer at Wing Assistant in Toronto. Remote, full-time, paying $29k–$35k. Posted June 23, 2026.

- Company: Wing Assistant
- Location: Toronto
- Workplace: Remote
- Job type: Full-time
- Pay: $29k–$35k
- Posted: 2026-06-23
- Apply: https://jobs.lever.co/getwingapp/43fbd901-d42b-4077-8b0f-999421a5b64e/apply
- Source: https://jobmagic.ai/jobs/sales-enablement-trainer-wing-assistant-h7wp99

## Requirements

- 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.

## Description

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team — not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day. This is a coach who has *carried a quota and closed*, and uses that credibility to make real, measurable improvements on the floor.

If your first instinct when a deal stalls is "let me see the thread and the call recording" — read on.

### 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.

### Requirements

**You'll thrive here if you**

- 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.

 

**Nice to have
**
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).

 

### Why the Role

**How the role actually runs — fast loop, not slow decks:** **Listen → Diagnose → Build → Intervene.**

- You hear the calls, name the specific problem, build the fix the same day, and get it into reps' hands immediately. A pattern that shows up Monday should have a tested correction in motion by midweek.

**Why this role**

- You're joining at a build moment. You'll start lean and resourceful — and as the program proves it drives revenue, it ears more investment and room to grow. This is a roll-up-your-sleeves, multi-hat seat for someone who wants to own the engine, not manage a slide deck.