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.ResponsibilitiesSitinthecalls—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.RequirementsYou’llthrivehereifyouHavepersonallysoldandclosed—ideallyoutbound/high-volumeB2B—andcanshowyournumbers.Writesalescopythatconvertsandcanexplainwhyitworks.Arecomfortableoncameraandcanproducecleantrainingvideoswithoutaproductionteam.CanstructureanA/Btest,readtheresulthonestly,andmakethecall.Coachwithoutcrushing—youleaverepsbetterandmoreconfident.Movefast:adiagnosisbecomesausablefixinhours,notweeks.KnowyourwayaroundaCRM(Hubspotplus)andasalessequencingtool.NicetohaveExperience 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 RoleHowtheroleactuallyruns—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.WhythisroleYou'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#J-18808-Ljbffr

📌 Sales Enablement Trainer - $29,000 - $35,000 A Year (Winnipeg)
🏢 Wing Assistant
📍 Winnipeg