Sales Enablement Trainer

Medium; Toronto (KS); On-site; USD 29,000 - 35,000; Full time

Job summary

Medium is hiring a Sales Enablement Trainer to enhance the skills of their sales team. This role involves directly analyzing sales calls, rewriting scripts, and coaching reps to improve performance based on real-world data.

The ideal candidate has a successful sales background, is skilled in effective coaching, and can produce training materials independently. You'll play a crucial role in shaping the sales process and driving revenue growth.

Qualifications

• Proven track record in sales with a focus on outbound and high-volume B2B.
• Ability to coach sales reps effectively without discouragement.
• Comfortable producing training videos independently.

Responsibilities

• Analyze sales calls and identify where improvements can be made.
• Rewrite sales scripts and sequences for better conversion rates.
• Implement A/B tests for various sales tactics.

Skills

Sales copywriting

B2B sales experience

Coaching skills

A/B testing

CRM proficiency

Tools

HubSpot

Pipedrive

Sales sequencing tools (Apollo, Outreach)

Job 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 carriedaquotaandclosed, 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