Sales Enablement & Performance Leader

Jobtailor; Northern (KY); Hybrid; USD 95,000 - 130,000; Full time

Job summary

Jobtailor in the United States (Northern Kentucky area) seeks an experienced sales enablement leader to build and optimize the inbound and outbound sales engine. You will lead the team responsible for sequences, playbooks, and AI-assisted tools, aligning content with funnel metrics and CRM data.

The role includes coaching SDRs and AEs, improving follow-up, and ensuring compliance of sales information. You will own content powering the AI chat assistant and drive calibration sessions on live

Qualifications

• 4+ years in inside sales or revenue roles.
• 2+ years coaching sales teams.
• Proven track record building sales systems from scratch.
• Experience improving follow-up, pipeline conversion, or show rates.
• Strong inbound sales understanding and lead management.
• Coaching reps on discovery, objection handling, urgency, and progression.
• Hands-on experience building email/chat sequences across channels.
• Strong CRM discipline with platforms such as HubSpot or Salesforce.
• Data-driven diagnosis of funnel problems and target setting.
• Excellent written and verbal English communication.

Responsibilities

• Build sales assets such as sequences, talk tracks, objection-handling guides, battle cards, and demo collateral.
• Identify gaps in the sales motion and create tools, processes, or content to close them.
• Evaluate and implement AI-enabled sales tools, conversation intelligence, and automation.
• Manage and develop the inbound follow-up team, including SDRs and Sales Associates.
• Conduct 1:1s, coach performance, hire as the team scales, and manage the Sales Trainer.
• Own the Sales Associate and Account Executive pairing model, cadence standards, ownership rules, and CRM hygiene.
• Design, write, and A/B test email and chat follow-up sequences.
• Manage no-show recovery, rebooking, reactivation, and closed-lost opportunity campaigns.
• Reduce stage-to-stage funnel drop-off using reply rate, re-engagement rate, and conversion metrics.
• Oversee channel-partner leads and opportunities, including ownership, follow-up, reporting, and performance tracking.
• Review recorded calls and demos using a written sales scorecard and maintain monthly review coverage.
• Coach Account Executives on discovery, objection handling, urgency, and securing second calls.
• Run calibration sessions and join live deals when representatives need support.
• Own the sales knowledge base and content powering the AI sales chat assistant.
• Ensure customer-facing sales claims and automated-channel information are accurate and compliant.
• Build and lead Wing Assistant's inbound sales performance engine for its AI-enabled workforce solutions.

Skills

Inside Sales

Sales Enablement

Coaching Teams

Data-Driven Decisions

CRM Discipline

Lead Management

Email Sequences

Conversation Intelligence

AI Sales Tools

Pipeline Optimization

Tools

HubSpot

Salesforce

AI Sales Chat Assistant

Sales Scorecard

Automation Tools

Job description

Jobtailor in the United States (Northern Kentucky area) seeks an experienced sales enablement leader to build and optimize the inbound and outbound sales engine. You will lead the team responsible for sequences, playbooks, and AI-assisted tools, aligning content with funnel metrics and CRM data.

The role includes coaching SDRs and AEs, improving follow-up, and ensuring compliance of sales information. You will own content powering the AI chat assistant and drive calibration sessions on live