Sales Enablement Trainer

Getwingapp; San Antonio (TX); On-site; USD 70,000 - 90,000; Full time

Job summary

Getwingapp in San Antonio, Texas, is seeking a Sales Enablement Trainer focused on enhancing the sales team's efforts. This role involves analyzing calls to identify problems and coaching reps on improving their outreach strategies.

You will have the opportunity to implement immediate improvements, produce training content, and develop effective sales techniques. Ideal candidates are experienced in B2B sales and have a knack for coaching and engaging with sales teams through their challenges.

Qualifications

• Experience in outbound/high-volume B2B sales.
• Ability to produce training videos without a production team.
• Comfort in coaching and enhancing rep confidence.

Responsibilities

• Analyze calls to determine where deals are lost.
• Rewrite sales copy and run A/B tests to improve conversion.
• Coach reps in one-on-one sessions using real calls.

Skills

Sales copywriting

Coaching ability

A/B testing

Comfort on camera

Tools

CRM (Hubspot)

Sales sequencing tools (Apollo, Outreach)

Video editing software

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.

You'll thrive here if you

• Havepersonallysoldandclosed—ideallyoutbound/high-volumeB2B—andcanshowyournumbers.
• Writesalescopythatconvertsandcanexplainwhyitworks.
• Arecomfortableoncameraandcanproducecleantrainingvideoswithoutaproductionteam.
• CanstructureanA/Btest,readtheresulthonestly,andmakethecall.
• Coachwithoutcrushing—youleaverepsbetterandmoreconfident.
• Movefast:adiagnosisbecomesausablefixinhours,notweeks.
• KnowyourwayaroundaCRM(Hubspotplus)andasalessequencingtool.

Nice to have

• 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).

How the role actually runs—fast loop, not slow decks:

• 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.

Why this role

• 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.