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Sales Enablement Trainer

Wing Assistant
8 hours ago
Full-time
On-site
Chicago, IL

JobsCloseBy Editorial Insights

Wing Assistant seeks a hands on Sales Enablement Trainer to raise a high velocity B2B team. The ideal candidate has personally closed deals, translates credibility into repeatable playbooks, and will sit in calls to diagnose where deals stall, rewrite copy and cadences, run A/B tests, tune outbound timing and messaging, coach one on one, and build an objection handling playbook plus video training. You should have quota carried success, write copy that converts, and be comfortable on camera with HubSpot and a sequencing tool. Nice to have virtual staffing or video editing experience. Apply with concrete metrics, samples of your work, and a plan for rapid impact in Chicago, onsite, full-time.

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.