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

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 rapid: 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:

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 earns 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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📌 Sales Enablement Trainer (Winnipeg)
🏢 Wing Assistant
📍 Winnipeg