Head of Sales Performance

Wing Assistant

Head of Sales Performance building Wing Assistant’s AI-enabled workforce sales engine. Improving inbound conversion through sales systems, coaching, automation, and disciplined follow-up.

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

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in building and managing sales systems, tools, and processes to enhance sales performance. Proficient in coaching sales teams, utilizing data for performance management, and implementing AI-enabled sales tools.

Highest-signal resume keywords

Sales EnablementCoaching Sales TeamsBuilding Sales SequencesCRM DisciplineData-Driven Performance Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Inside SalesSales DevelopmentSales Systems BuildingPipeline ConversionObjection HandlingFollow-Up StrategiesSales Collateral CreationEmail Sequence DesignPerformance EvaluationSales Training

Soft Skills

Written CommunicationVerbal CommunicationCoachingTeam ManagementFeedback Delivery

Tools & Technologies

HubSpotSalesforceAI-Enabled Sales ToolsConversation IntelligenceSales Automation Platforms

Industry Keywords

Inbound Sales FunnelsLead ManagementSales Claims ManagementHigh-Growth StartupSaaS

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 1:1s, coach performance, hire as the team scales, and own the Sales Associate–Account Executive pairing model
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 email and chat follow-up sequences
Track reply rate, re-engagement rate, conversion, show rates, and funnel drop-off
Build no-show recovery, rebooking, reactivation, and closed-lost opportunity campaigns
Oversee channel-partner leads and opportunities, including ownership, follow-up, reporting, and performance evaluation
Review recorded calls and demos using a written sales scorecard and maintain monthly call-review coverage
Coach Account Executives and join live deals when support is needed
Run calibration sessions for consistent scoring and coaching standards
Own the sales knowledge base and content powering the AI sales chat assistant
Keep customer-facing information accurate, current, compliant, and aligned with sales claims

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 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
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
Preferred: experience managing SDRs/Sales Associates and Account Executives
Preferred: experience owning sales onboarding, training, and rep ramp-up programs
Preferred: experience with 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
Preferred: experience in a high-growth startup, SaaS, staffing, outsourcing, or technology-enabled services company
Preferred: experience managing channel-partner leads
Preferred: familiarity with compliance, sales claims management, and customer-facing knowledge bases

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