Posted 5 months ago
Sales Enablement Trainer
@ Wing Assistant
Toronto, Ontario
Overview
Wing Assistant is hiring a hands-on Sales Enablement Trainer to improve the emails, calls, and outbound cadences its sales reps use daily. The role involves listening to live and recorded calls, rewriting underperforming copy, running A/B tests, coaching reps one-on-one, and producing video training. Full-time.
Responsibilities:
- Listen to live and recorded sales calls to find where deals are lost
- Rewrite emails, scripts, and sequences that are not converting
- Run A/B tests on sales emails, call openers, demos, and video outreach
- Build and tune outbound cadences and coach reps one-on-one
Requirements summary:
- Personally sold and closed, ideally outbound high-volume B2B
- Writes sales copy that converts and can explain why
- Comfortable on camera and able to produce clean training videos
- Knows a CRM (HubSpot plus) and a sales sequencing tool
Tools & skills
Source and dates
Employer career site / ATS feed · lever
- Employer posting date
- 2026-06-23
- First seen by our source
- 2026-10-08
- Source record updated
- 2026-10-09
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Mid level |
| Department | Sales |
| Hours per week | 40 (estimated) |
| Work setting | Office, Home |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Languages | English |
Summary and details written by AI from the posting; the employer’s posting is the authority.
Wing Assistant
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
We're the World's Best Assistant. Hit "Learn More" to speak to an expert about transforming your business! 🚀
Full company description
Wing provides small businesses, startups, execs, and enterprises with the top 1% of remote talent to take over recurring work such as Social Media Management, Executive Assistance, Data Entry, Sales Calling, etc. Wing is your incredible, yet super affordable, team member to whom you can delegate excess work while you do the important things to grow your business.
- LinkedIn followers
- 179,512
- People associated on LinkedIn
- 1,223
- Reported office locations
- 2150 Shattuck Ave, Berkeley, California 94704, US
- Business categories
- CRM
- Virtual Assistant
- Software
- SaaS
- Internet
- Staffing, Recruitment & Subcontracting
- Human resources and staffing
- Other recorded names
- Wing Assistant
- Specialties
- Internet
- Personal Assistance
- Virtual Assistance
- Data Entry
- Spreadsheet Management
- Outbound Communication
- Inbound Communication
- Planning
- CRM Management
- Concierge Services
- Calendaring
- Scheduling
- File Management
- Purchases
- CRM
- Employee Onboarding
- Sales Calling
- SDRs
- and Social Media Management
- Profile identifies a recruitment agency
- No
- Reported total investment
- 2,205,000
Currency and observation date were not supplied; this is not a current valuation or a funding round.
Wing provides small businesses, startups, execs, and enterprises with the top 1% of remote talent to take over recurring work such as Social Media Management, Executive Assistance, Data Entry, Sales Calling, etc. Wing is your incredible, yet super affordable, team member to whom you can delegate excess work while you do the important things to grow your business.
| Field | Value |
|---|---|
| Industry | Internet Marketplace Platforms |
| Company size | 1,001-5,000 employees |
| Headquarters | Berkeley, California |
| Organization type | Privately Held |
| Year founded | 2018 |
| Specialties | InternetPersonal AssistanceVirtual AssistanceData EntrySpreadsheet ManagementOutbound CommunicationInbound CommunicationPlanningCRM ManagementConcierge Services |
| Open jobs on Jobsy | 9 |
| View page |
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.
You'll thrive here if you
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
- 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.
How the role actually runs — fast loop, not slow decks: Listen → Diagnose → Build → Intervene.
Why this role
Journal
Only you can see this. Kept on this device, and in your account when you sign in.