Sales Enablement Trainer

Medium; Denver (CO); On-site; USD 29,000 - 35,000; Full time

Job summary

Medium is looking for a Sales Enablement Trainer in Denver, Colorado. This hands-on role involves improving sales team performance through enhanced email, call scripts, and training methods. Ideal candidates will have a proven track record in sales, experience in writing compelling sales copy, and skills in video production.

The position offers an engaging environment where you'll actively contribute to impactful training programs. The salary ranges from $29,000 to $35,000 per year based on experience.

Qualifications

• Proven track record in sales, preferably B2B.
• Ability to write converting sales copy.
• Experience in creating training videos.

Responsibilities

• Analyze call recordings to identify deal losses.
• Edit sales scripts and materials to improve conversion.
• Conduct A/B tests on emails and calls.

Skills

Sales experience

Sales copywriting

A/B testing

Coaching

CRM software

Video production

Tools

Hubspot

Pipedrive

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