Wing Assistant

4 weeks ago

Sales Enablement Trainer

✓ Verified Job

Canonical indexed version, validated from employer's careers page.

Source: Company careers pageValidated by: Fursa AI

Last checked: 12 hours agoStatus: Live

Job Summary

Hands-on Sales Enablement Trainer to level up our sales team by improving the actual emails, calls, and cadences our reps use every day. This role requires a quota-carrying, outbound B2B background, with the ability to write high-converting copy, produce training videos, and optimize outreach through A/B testing. You’ll own the engine, not just slides, and move quickly to drive revenue.

Location: Toronto

Workplace: Remote

Employment Type: Full time

Job Function: Education & Training

Key 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.

Pay and Benefits

Salary: USD 29,000 - 35,000 annually

Key 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 reps without crushing—you leave reps better and more confident.

Experience:B2BSaaSOutbound

Skills:CommunicationPresentationTrainingVideo productionCopywritingCoaching

Languages:English

Tech Stack:HubSpotPipedriveCRMSalesloftOutreachApolloVideo editing

Company Brief

Wing Assistant

Provides remote virtual assistant and administrative support services, matching businesses with trained assistants for tasks like scheduling, email management, research, and operations to improve productivity and reduce overhead.

Industry: Recruitment Agencies

Website

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Wing Assistant

4 weeks ago

Sales Enablement Trainer

✓ Verified Job

Canonical indexed version, validated from employer's careers page.

Source: Company careers pageValidated by: Fursa AI

Last checked: 12 hours agoStatus: Live

Job Summary

Location: Toronto

Workplace: Remote

Employment Type: Full time

Job Function: Education & Training

Key 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.

Pay and Benefits

Salary: USD 29,000 - 35,000 annually

Key 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 reps without crushing—you leave reps better and more confident.

Experience:B2BSaaSOutbound

Skills:CommunicationPresentationTrainingVideo productionCopywritingCoaching

Languages:English

Tech Stack:HubSpotPipedriveCRMSalesloftOutreachApolloVideo editing

Company Brief

Wing Assistant

Industry: Recruitment Agencies

Website