Head of Sales

• 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

• 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 feedback
  
  Hands-on experience building sales sequences across email, chat, SMS, or other follow-up channels
• Strong CRM discipline and experience with platforms such as Hub Spot 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

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.

• Sales Enablement
• Coaching Sales Teams
• Building Sales Systems
• CRM Discipline
• Data-Driven Performance Management

• Sales Development
• Pipeline Conversion
• Follow-Up Sequences
• Objection Handling
• Lead Management
• Sales Cycle Performance
• Performance Tracking
• Email A/B Testing
• Conversation Intelligence
• AI Sales Tools

• Written Communication
• Verbal Communication
• Coaching
• Performance Evaluation
• Team Management

• Inbound Sales Funnels
• Sales Motion
• Sales Performance Engine
• Channel-Partner Leads
• Sales Knowledge Base

• Hub Spot
• Salesforce
• AI Sales Chat Assistant
• Sales Scorecard
• Automation Tools