Head of Sales Performance

Jobtailor

Northern (KY)

Hybrid

USD 95,000 - 130,000

Full time

11 days ago

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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

Build sales assets including 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

Requirements

At least 4 years of experience in inside sales, sales development, sales enablement, revenue operations, or a similar commercial role
At least 2 years of experience managing or coaching a sales team
Track record of building sales systems, tools, or programs from scratch
Proven experience improving follow-up, pipeline conversion, show rates, or sales-cycle performance
Strong understanding of inbound sales funnels, lead management, and mid-funnel conversion
Experience coaching sales representatives on discovery, objection handling, urgency, and deal progression
Ability to review sales calls, identify performance gaps, and provide actionable feedbackHands-on experience building sales sequences across email, chat, SMS, or other follow-up channels
Strong CRM discipline and experience with platforms such as HubSpot or Salesforce
Ability to use data to diagnose funnel problems, set targets, and manage performance
Strong written and verbal English communication skills
Willingness and ability to work Pacific Time hours

Core Competencies

Demonstrates expertise in building and managing sales systems, tools, and processes to enhance sales performance and conversion metrics. Proficient in coaching sales teams and utilizing data-driven insights to optimize inbound sales funnels and lead management.

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