Sales Enablement Trainer

Wing Assistant

Sales Enablement Trainer at Wing Assistant, enhancing sales team capabilities through direct coaching and training. Focused on real-time improvements in sales communication and process.

Posted 6/23/2026full-timeRemote • 🇨🇦 CanadaMid-LevelSenior💰 $29,000 - $35,000 per yearWebsite

Tech Stack

Tools & technologies

Apollo

About the role

Key responsibilities & impact

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

What you’ll need

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).

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account Wing Assistant Website LinkedIn All Job Openings 501 - 1000 employees 🤝 B2B ☁️ SaaS ⚡ Productivity 💰 $2.1M Seed Round on 2022-03 B2B
SaaS
Productivity Wing Assistant is a company specializing in providing virtual assistant services to businesses worldwide. The company offers a wide range of services including general virtual assistant work, executive assistance, customer service, bookkeeping, and digital marketing. Wing Assistant aims to enhance productivity for startups and enterprise teams by delegating tasks to dedicated virtual assistants, reducing operational load, and enabling businesses to focus on core activities. Their services are accessible via a subscription model, providing flexible and cost-effective solutions compared to traditional hiring methods. Clients benefit from a dedicated assistant model where the assistant works solely for their business, gaining a deeper understanding of their processes over time. Sales Enablement Trainer Job not on LinkedIn 🔥 4 minutes ago 🇨🇦 Canada – Remote 💵 $29k - $35k / year ⏰ Full Time 🟡 Mid-level 🟠 Senior 📊 Sales Operations Apply Now Find Hiring Managers Customize resume + cover letter Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 Description
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). Apply Now 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score Similar Jobs Senior Technical Sales Enablement Manager 🕒 May 29 Docker, Inc 51 - 200 Website LinkedIn All Job Openings Senior Technical Sales Enablement Manager designing and scaling onboarding and technical enablement programs for Docker’s sales teams. Collaborating across departments to enhance sales performance and learning. 🇨🇦 Canada – Remote 💵 $120.4k - $172k / year 💰 $105M Series C on 2022-03 ⏰ Full Time 🟠 Senior 📊 Sales Operations Associate Vice President – Sales Enablement 🕒 May 23 Info-Tech Research Group 1001 - 5000 🤝 B2B 🏢 Enterprise Website LinkedIn All Job Openings Strategic leadership role driving sales performance across Info-Tech and Vendor Services. Focus on sales enablement strategies for onboarding, training, and process adoption across North America, EMEA, and APAC. 🇨🇦 Canada – Remote ⏰ Full Time 🟢 Junior 🟡 Mid-level 📊 Sales Operations Associate Vice President – Sales Enablement 🕒 May 21 Info-Tech Research Group 1001 - 5000 🤝 B2B 🏢 Enterprise Website LinkedIn All Job Openings AVP of Sales Enablement driving sales performance across Info-Tech Research Group. Responsible for new hire onboarding, sales training, and leadership development in multiple regions. 🇨🇦 Canada – Remote ⏰ Full Time 🟢 Junior 🟡 Mid-level 📊 Sales Operations Senior Sales Operations Lead 🕒 May 18 Zendesk 5001 - 10000 ☁️ SaaS 🤝 B2B Website LinkedIn All Job Openings Strategy & Operations Partner at Zendesk leading global Professional Services initiatives and optimizing operational processes. Focused on data insights to enhance customer engagement in a high-growth SaaS environment. 🇨🇦 Canada – Remote 💰 Grant on 2019-09 ⏰ Full Time 🟠 Senior 📊 Sales Operations Senior Sales Operations Analyst 🕒 May 15 Cision France 1001 - 5000 🤝 B2B 📱 Media Website LinkedIn All Job Openings Support sales and revenue teams through data analysis, reporting, and operational execution. Contributing to the efficiency and visibility across the sales lifecycle at Cision. 🇨🇦 Canada – Remote 💵 $79k - $94k / year ⏰ Full Time 🟠 Senior 📊 Sales Operations View More Sales Operations Jobs 🌐 Worldwide Built by Lior Neu-ner. I'd love to hear your feedback — Get in touch via DM or support@remoterocketship.com Search Search Jobs by country Search jobs by city Search jobs by job title Search entry-level jobs Search junior-level jobs Search senior-level jobs Search jobs by tech stack Search jobs by contract type Search remote internships Search remote part-time jobs Remote jobs Anywhere in the World Companies Hiring Anywhere in the World Companies Hiring Sales People Anywhere in the World Companies Hiring Software Engineers Anywhere in the World Resources Advice Tips for finding remote jobs Interview questions and answers Resume examples Cover letter examples Post a job Affiliates Privacy policy Terms of service Job board SEO course AI Apply Copilot OpenClaw job finder Jobs by Country Remote jobs anywhere in the world (Worldwide remote jobs) Remote jobs United States Remote jobs Australia Remote jobs Brazil Remote jobs Canada Remote jobs France Remote jobs Ireland Remote jobs Germany Remote jobs Netherlands Remote jobs Spain Remote jobs UK Popular Jobs Remote data analyst jobs Remote customer support jobs Remote executive assistant jobs Remote marketing jobs Remote product designer jobs Remote product manager jobs Remote project manager jobs Remote recruiter jobs Remote sales jobs Remote software engineer jobs Jobs by Type Remote full-time jobs Remote part-time jobs Remote contract jobs Remote internship jobs Remote entry-level jobs Remote jobs with no experience required Remote junior jobs (1-3 years of experience) Digital nomad jobs Remote jobs with no degree required Freelance remote jobs Temporary remote jobs Remote jobs hiring now Stay at home mom jobs

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Hard Skills & Tools

A/B testingsales copywritingvideo productionobjection handlingsales sequencingCRM managementsales enablementdata analysistraining developmentcoaching

Soft Skills

communicationcoachingadaptabilityproblem-solvingconfidence buildingtime managementcollaborationcreativityleadershipanalytical thinking