Sales Enablement Trainer

Sales Enablement Trainer

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.

• 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.

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)

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.

• 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