Sales Enablement Trainer

Wing Assistant; Canada; On-site; CAD 60,000 - 80,000; Full time

Job summary

Wing Assistant is seeking a Sales Enablement Trainer to enhance the sales team's performance. The role involves analyzing calls, improving sales scripts, and coaching reps effectively on a fast-paced basis.

The ideal candidate has a strong background in outbound B2B sales, can produce training videos, and has a knack for A/B testing. Join us to take ownership of the sales engine and make measurable impacts.

Qualifications

• Proven track record in outbound/high-volume B2B sales.
• Ability to write and explain effective sales copy.
• Comfortable creating training videos independently.

Responsibilities

• Analyze calls to identify lost deals.
• Rewrite and test sales scripts for effectiveness.
• Train sales reps to improve performance.

Skills

Sales copywriting

Coaching

B2B Sales

A/B Testing

CRM knowledge

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 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

• 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:

• 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 earns 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