Sales Enablement Trainer

Wing Assistant; Chicago (IL); On-site; USD 29,000 - 35,000; Full time

Job summary

Wing Assistant is seeking a hands-on Sales Enablement Trainer to enhance the sales team's performance by improving emails, calls, and cadences. The role requires someone who has personally sold and closed effectively, creating measurable improvements on the sales floor.

Responsibilities include analyzing live and recorded calls, rewriting non-converting scripts, and coaching reps to ensure success. The salary range is $29,000 - $35,000 annually.

Qualifications

• Experience in outbound or high-volume B2B sales with proven numbers.
• Ability to write sales copy that converts and provide rationales.
• Comfortable on camera, able to create training videos independently.

Responsibilities

• Analyze calls to identify deal losses.
• Revise sales scripts and sequences that aren't effective.
• Test different sales tactics and keep the successful ones.

Skills

Sales copywriting

Outbound B2B sales

Coaching

A/B testing

Video production

Tools

HubSpot CRM

Sales sequencing tools

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.

Ifyourfirstinstinctwhenadealstallsis"letmeseethethreadandthecallrecording"—readon.

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