Sales Enablement Trainer

Job summary

The role focuses on improving sales conversion by analyzing calls and rewriting scripts, emails, and cadences. It involves coaching reps one-on-one and creating video training modules to accelerate onboarding and performance.

Job details

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. \n 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. \n $29,000 - $35,000 a year \n

What you’ll do

The role focuses on improving sales conversion by analyzing calls and rewriting scripts, emails, and cadences. It involves coaching reps one-on-one and creating video training modules to accelerate onboarding and performance.

Requirements

Candidates must have a proven track record of closing B2B outbound deals and the ability to write high-converting sales copy. Proficiency with CRMs and sales sequencing tools, along with the ability to produce training videos, is required.

Listed skills

• Sales · Preferred
• Training · Preferred
• Coaching · Preferred
• Onboarding · Preferred
• Outbound · Preferred
• CRM · Preferred
• Correction · Preferred
• Lean · Preferred
• Objection Handling · Preferred
• Production · Preferred
• Resourceful · Preferred
• Time · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Sales Enablement
• Sales Coaching
• Copywriting
• A/B Testing
• CRM Management
• Outbound Sales
• Video Production
• Objection Handling
• Curriculum Development
• Sales Sequencing

Job areas

• Sales
• Education
• Management & Leadership
• Marketing

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