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
Sales Enablement Trainer in Ottawa employer: Wing Assistant
Join a dynamic virtual talent company in Toronto that prioritizes innovation and employee well-being. With a strong focus on professional growth, we offer competitive salaries, remote work flexibility, and a collaborative culture that encourages creativity and skill development. As a Remote Website Manager, you'll be part of a team that values your expertise in CRO and WordPress, providing you with the opportunity to make a significant impact on our clients' web performance.
