Sales Enablement Trainer

Wing Assistant; United States; Remote; USD 29,000 - 35,000; Full time

Job summary

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 emails, calls, and cadences reps use every day.

You will sit in on live calls, rewrite copy and scripts, build outbound cadences, and coach reps one-on-one until fixes become reflexes, with video training modules to ramp new hires.

Qualifications

• Have personally sold and closed—ideally outbound/high-volume B2B—and can show your numbers.
• Writes sales copy that converts and can explain why it works.
• Are comfortable on camera and can produce clean training videos without a production team.
• Can structure an A/B test, read the results honestly, and make the call.
• Coach reps without crushing—you leave them better and more confident.
• Move fast: a diagnosis becomes a usable fix in hours, not weeks.
• Know your way around a CRM (HubSpot plus) and a sales sequencing tool.

Responsibilities

• Sit in on live and recorded calls to identify where deals are being lost.
• Rewrite copy, scripts, and sequences that aren’t converting, and prove the new version works.
• A/B test sales emails, call openers, demos, and tactics; keep the winners, kill the losers.
• Build and tune outbound cadences so reps follow up at the right time, channel, and message.
• Coach reps one-on-one on real calls and develop an objection-handling playbook.
• Produce a video training series and self-serve modules with assessments to ramp; keep reps sharp.

Skills

Outbound sales

Sales copywriting

On-camera training

A/B testing

Coaching

CRM proficiency

Rapid problem solving

Tools

HubSpot

Pipedrive

Apollo

Outreach

Salesloft

Instantly

Smartlead

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,readtheresulhonestly,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