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Sales Enablement Trainer

Wing Assistant

toronto, on, Canada Full-time July 12, 2026

Found 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

  • Sitinthecalls—liveandrecorded—andfindexactlywheredealsarebeinglost.
  • Rewritethecopy,scripts,andsequencesthataren'tconverting,andprovethenewversionworks.
  • A/Btestsalesemails,callopeners,demopitches,andtacticslikepersonalizedvideo—keepthewinners,killthelosers.
  • Buildandtuneoutboundcadencessorepsfollowupattherighttime,ontherightchannel,withtherightmessage.
  • Coachrepsone-on-oneonrealcallsandbuildtheobjection-handlingplaybookforourmarket—thendrillituntilit'sreflexive.
  • ...

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