# Sales Enablement Trainer at Wing Assistant

> Remote · Canada · Unspecified · Other · open. Source: https://alderhq.app/jobs/lever%3Agetwingapp%3Ad93b5073-38ff-4e15-95ea-6464a5497b05 (read 2026-11-06).

## Facts (observed)

- Company: [Wing Assistant](https://alderhq.app/companies/wing-assistant)
- Location text: Canada
- Where it can be done from (inferred): Remote · Canada (evidence: "Location: Canada")
- Posted: 2026-06-23 (136 days ago)
- First seen by alder: 2026-11-03 · last verified: 2026-11-04
- Reposted: 0 times · edited: 0 times
- Apply on the employer's site: https://jobs.lever.co/getwingapp/d93b5073-38ff-4e15-95ea-6464a5497b05

## Pay and sponsorship

- Posted pay: $29k–$35k per year (from the listing's pay field)
- Market band for similar posted roles (Canada, n 85): p25 $45k, median $73k, p75 $95k

## Description (the employer's text)

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.

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Data: alder (https://alderhq.app). Cite https://alderhq.app/jobs/lever%3Agetwingapp%3Ad93b5073-38ff-4e15-95ea-6464a5497b05 and the date you read it. Observed facts come from the employer's own listing; location reach, level, family and skills are inferences.