Role overview

Qualifications

Have personally sold and closed, ideally outbound/high-volume B2B, and can show your numbers
Write 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 result honestly, and make the call

Responsibilities

Sit in the calls — live and recorded — and find exactly where deals are being lost
Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works
A/B test sales emails, call openers, demo pitches, and tactics like personalized video — keep the winners, kill the losers
Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message

Key facts

Remote from: Canada, Colorado (USA), Florida (USA), Illinois (USA), New Mexico (USA), North Carolina (USA), Oklahoma (USA), Texas (USA), Washington (USA)
Full time
Sales Enablement
English

Hard skills

A/B Testing Small Business Sales Sales Strategy Microsoft Dynamics CRM Video Production Staffing Software Utilities BPO Pipedrive Video Editing Sales Automation Software

Other skills

Coaching
Problem Solving
Communication
Time Management

About the company

Wing Assistant

Outsourcing & Offshoring

Wing provides small businesses, startups, execs, and enterprises with the top 1% of remote talent to take over recurring work such as Social Media Management, Executive Assistance, Data Entry, Sales Calling, etc. Wing is your incredible, yet super affordable, team member to whom you can delegate excess work while you do the important things to grow your business.

Company details

Company typeScaleup

IndustryOutsourcing & Offshoring

Company size1001 - 5000

Links

Website LinkedIn See all jobs

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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 carried a quota and closed, 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

Sit in the calls — live and recorded — and find exactly where deals are being lost.

Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works.

A/B test sales emails, call openers, demo pitches, and tactics like personalized video — keep the winners, kill the losers.

Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message.

Coach reps one-on-one on real calls and build the objection-handling playbook for our market — then drill it until it's reflexive.

Produce a video training series and self-serve modules with assessments, so new reps ramp fast and tenured reps keep sharpening.

Requirements

You'll thrive here if you

Have personally sold and closed — ideally outbound/high-volume B2B — and can show your numbers.

Write 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 result honestly, and make the call.

Coach without crushing — you leave reps 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.

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).

Why the Role

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

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.

Apply once. Then go straight to the hiring manager.

After you apply, unlock the direct contact details of the people who actually make the call. A quick follow-up makes you 5x more likely to land an interview.