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

Sitinthecalls—liveandrecorded—andfindexactlywheredealsarebeinglost.

Rewritethecopy,scripts,andsequencesthataren'tconverting,andprovethenewversionworks.

A/Btestsalesemails,callopeners,demopitches,andtacticslikepersonalizedvideo—keepthewinners,killthelosers.

Buildandtuneoutboundcadencessorepsfollowupattherighttime,ontherightchannel,withtherightmessage.

Coachrepsone-on-oneonrealcallsandbuildtheobjection-handlingplaybookforourmarket—thendrillituntilit'sreflexive.

Produceavideotrainingseriesandself-servemoduleswithassessments,sonewrepsrampfastandtenuredrepskeepsharpening.

Requirements
You’llthrivehereifyou

Havepersonallysoldandclosed—ideallyoutbound/high-volumeB2B—andcanshowyournumbers.

Writesalescopythatconvertsandcanexplainwhyitworks.





Arecomfortableoncameraandcanproducecleantrainingvideoswithoutaproductionteam.

CanstructureanA/Btest,readtheresulthonestly,andmakethecall.

Coachwithoutcrushing—youleaverepsbetterandmoreconfident.

Movefast:adiagnosisbecomesausablefixinhours,notweeks.

KnowyourwayaroundaCRM(Hubspotplus)andasalessequencingtool.

Nicetohave
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
Howtheroleactuallyruns—fastloop,notslowdecks: 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.

Whythisrole

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.

$29,000 - $35,000 a year

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📌 Sales Enablement Trainer (Ontario)
🏢 Wing Assistant
📍 Ontario