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About the Role

Wing Assistant is seeking a Head of Sales Performance to build and optimize the inbound sales engine, focusing on driving performance from initial contact through to closing deals. This is a hands-on, builder-focused role requiring the creation of essential sales tools, sequences, coaching systems, and standards to enhance team performance.

Responsibilities

• Build the Sales Performance Toolkit, including sequences, talk tracks, objection-handling guides, and demo collateral.
• Identify and address gaps in the sales motion by creating necessary tools, processes, or content.
• 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 regular 1:1s, coach performance, and hire team members as needed.
• Own the pairing model between Sales Associates and Account Executives.
• Establish cadence standards, ownership rules, and CRM hygiene expectations.
• Manage the Sales Trainer and oversee onboarding and ramp-up for new sales hires.
• Design, write, and A/B test follow-up sequences across email and chat.
• Build and manage the no-show recovery process for cancellations and missed demos.
• Reduce stage-to-stage drop-off across the funnel.
• Oversee the handling of leads and opportunities generated through channel partnerships.
• Establish clear ownership, follow-up, and reporting standards for partner-sourced opportunities.
• Track channel partner performance and evaluate effectiveness.
• Review recorded calls and demos using a written sales scorecard.
• Maintain a fixed monthly call-review coverage target for every representative.
• Coach Account Executives on discovery, objection handling, urgency, and securing second calls.
• Run regular calibration sessions to ensure consistent scoring and coaching standards.
• Join live deals to support representatives in moving opportunities forward.
• Own the sales knowledge base as the company's single source of truth.
• Maintain content for the AI sales chat assistant.
• Establish a regular review cadence for customer-facing information.
• Ensure claims made by sales representatives and automated channels are accurate and compliant.

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.
• A 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 clear, actionable feedback.
• Hands-on experience building sales sequences across email, chat, SMS, or other follow-up channels.
• Strong CRM discipline and experience working with platforms such as HubSpot or Salesforce.
• Comfortable using 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.

Skills

• Sales Performance Management
• Sales System Building
• Sales Tool Implementation
• AI-enabled Sales Tools
• Conversation Intelligence
• Sales Automation
• Team Leadership
• Performance Coaching
• Sales Onboarding
• Sales Sequence Design
• A/B Testing
• CRM Management (HubSpot, Salesforce)
• Data Analysis
• Sales Collateral Creation
• Channel Partner Management
• Sales Call Review
• Knowledge Base Management
• Compliance Management

Location

• Pacific Time Zone

Work Type

• Full-time

Experience Level

• Manager
• Senior

Salary/Compensations

• $125,000 - $155,000 a year

Benefits

• $125,000–$155,000 annual base salary, depending on experience
• Performance-based bonuses tied to individual and company goals
• Paid Time Off (PTO)
• Paid U.S. holidays
• Paid sick leave
• Health insurance
• Company-sponsored team events and offsites
• Clear opportunities for career advancement and expanded leadership responsibility

About the Company

• Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses.
• We help companies build high-performing teams across executive assistance, administrative support, customer support, sales support, recruiting, operations, and other critical business functions.