Sales Enablement Trainer

Wing Assistant; Tampa (CO); On-site; USD 29,000 - 35,000; Full time

Job summary

Medium is looking for a Sales Enablement Trainer in Tampa, Florida, to enhance the sales team’s effectiveness through direct coaching and practical training. This role involves analyzing sales calls, rewriting ineffective scripts, and implementing data-driven improvements quickly.

The ideal candidate has a strong background in outbound sales, is skilled in crafting effective sales copy, and is comfortable producing engaging training videos. This position offers a salary between $29,000 and $35,000 annually.

Qualifications

• Experience in outbound/high-volume B2B sales with proven numbers.
• Ability to write compelling sales copy and explain its effectiveness.
• Comfortable on camera, able to produce training videos independently.
• Can structure and analyze A/B tests effectively.
• Coaching skills that enhance reps' confidence and performance.
• Ability to implement fixes quickly.

Responsibilities

• Analyze live and recorded calls to identify lost deals.
• Rewrite sales scripts and conduct A/B tests for effectiveness.
• Develop outbound cadences for optimal follow-up timing.
• Coach sales reps one-on-one during real calls.
• Create video training modules for rep training.
• Respond to issues with timely solutions.

Skills

Sales copy writing

A/B testing

Coaching

CRM knowledge

Tools

Hubspot

Pipedrive

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.

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