Sales Enablement Trainer

Wing Assistant • Chicago, IL

5h • Remote

About The Position

Wing Assistant is hiring a hands-on Sales Enablement Trainer to level up our sales team. This role focuses on improving the actual emails, calls, and cadences used by sales representatives daily. The ideal candidate is a coach who has personally experienced selling and closing deals, using that credibility to drive measurable improvements. If your immediate reaction to a stalled deal is to review the communication threads and call recordings, this role is for you.

The role operates on a fast-loop model: Listen → Diagnose → Build → Intervene. Issues identified on Monday should have a tested correction implemented by midweek. This is a build moment where the program will grow with proven revenue impact, offering significant room for expansion. It's a hands-on, multi-faceted position for someone who wants to own the sales engine rather than manage presentations.

Requirements

• Proven track record of personally selling and closing deals, ideally in outbound/high-volume B2B, with verifiable numbers.
• Ability to write effective sales copy and articulate the reasoning behind its success.
• Comfortable on camera and capable of producing clean training videos without a dedicated production team.
• Proficiency in structuring A/B tests, interpreting results, and making data-driven decisions.
• Coaching skills that improve reps' confidence and performance without being discouraging.
• Ability to implement solutions rapidly, transforming diagnoses into usable fixes within hours.
• Familiarity with CRM systems (Hubspot preferred) and sales sequencing tools.

Nice To Haves

• Experience in virtual staffing, BPO, or managed services.
• Experience with Pipedrive or CRM automations.
• Video editing skills.
• Experience with sequencing tools such as Apollo, Outreach, Salesloft, Instantly, or Smartlead.
• Prior experience creating sales enablement assets like playbooks, battle cards, or certification programs.

Responsibilities

• Sit in on live and recorded calls to identify reasons for lost deals.
• Rewrite underperforming sales copy, scripts, and sequences, and validate new versions.
• A/B test sales emails, call openers, demo pitches, and tactics like personalized video, retaining effective strategies.
• Develop and optimize outbound cadences for timely, channel-appropriate, and effective follow-ups.
• Provide one-on-one coaching on real calls, build an objection-handling playbook specific to the market, and conduct drills.
• Create a video training series and self-serve modules with assessments for efficient new hire onboarding and continuous skill development for tenured reps.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed