Sales Enablement Trainer

Wing Assistant; Oklahoma City (OK); Hybrid; USD 29,000 - 35,000; Full time

Job summary

Wing Assistant is seeking a Sales Enablement Trainer to enhance our sales team's performance through hands-on training and targeted improvements. Your role will involve analyzing calls, rewriting scripts, and implementing effective sales strategies to boost conversion rates.

We seek someone with a strong background in outbound B2B sales, capable of producing high-quality training content. The position offers a salary range of $29,000 to $35,000 annually.

Qualifications

• Have personally sold and closed deals, ideally in outbound/high-volume B2B environments.
• Write sales copy that converts and can explain its effectiveness.
• Comfortable on camera and can produce training videos independently.
• Structured in A/B testing and able to assess results honestly.

Responsibilities

• Sit in live and recorded calls to identify deal loss points.
• Rewrite sales copy and test conversion efficacy.
• Build outbound cadences for timely follow-ups.
• Coach representatives on real calls and develop objection-handling playbooks.

Skills

Sales copy writing

Coaching

CRM proficiency

A/B testing

Tools

HubSpot

Pipedrive

Video editing 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