Head of Sales Performance

Wing Assistant

Head of Sales Performance building Wing Assistant’s AI-enabled workforce sales engine. Leading inbound follow-up, sales systems, coaching, funnel conversion, and AI sales technology adoption.

Posted 8/18/2026full-timeRemote • California • 🇺🇸 United StatesLead💰 $125,000 - $155,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in building and managing sales systems, tools, and processes to enhance performance and conversion rates. Proficient in coaching sales teams, utilizing AI-enabled tools, and ensuring compliance in customer-facing sales information.

Highest-signal resume keywords

Sales EnablementCoaching Sales TeamsBuilding Sales SequencesCRM ManagementAI-Enabled Sales Tools

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Inside SalesSales DevelopmentRevenue OperationsPipeline ConversionFollow-Up CampaignsSales Collateral CreationPerformance TrackingObjection HandlingLead ManagementSales Cycle Performance

Soft Skills

Written CommunicationVerbal CommunicationCoachingFeedback DeliveryTeam Management

Tools & Technologies

HubSpotSalesforceConversation Intelligence ToolsSales Automation PlatformsAI Sales Chat Assistant

Industry Keywords

High-Growth StartupSaaSStaffingOutsourcingTechnology-Enabled ServicesComplianceSales Claims Management

About the role

Key responsibilities & impact

Build sales assets including sequences, talk tracks, objection-handling guides, battle cards, and demo collateral
Identify gaps in the sales motion and build 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 regular 1:1s, coach performance, and hire as the team scales
Own the pairing model between Sales Associates and Account Executives
Establish cadence standards, ownership rules, and CRM hygiene expectations
Manage the Sales Trainer and own onboarding and ramp-up for new sales hires
Design, write, and A/B test follow-up sequences across email and chat
Manage no-show recovery, rebooking, and reactivation campaigns
Reduce stage-to-stage funnel drop-off
Oversee channel-partner leads and opportunities, including ownership, follow-up, reporting, and performance tracking
Review recorded calls and demos using a written sales scorecard
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 information and claims remain accurate and compliant
Build and lead the inbound sales performance engine for Wing Assistant's AI-enabled workforce solutions

Requirements

What you’ll need

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 clear, 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 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
Preferred: experience managing SDRs or Sales Associates and Account Executives
Preferred: experience owning sales onboarding, training, and rep ramp-up programs
Preferred: experience building no-show recovery, closed-lost reactivation, or aged-pipeline campaigns
Preferred: familiarity with AI-enabled sales tools, conversation intelligence, and sales automation platforms
Preferred: experience creating sales collateral, playbooks, or enablement content adopted floor-wide
Preferred: experience in a high-growth startup, SaaS, staffing, outsourcing, or technology-enabled services company
Preferred: experience managing leads generated through channel partnerships
Preferred: familiarity with compliance, sales claims management, and maintaining a customer-facing knowledge base

Benefits

Comp & perks

$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