Head of Sales Performance

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Wing Assistant

501 - 1000 employees

💼 Consulting

📣 Marketing

📦 Logistics

💰 $2.1M Seed Round on 2022-03

Consulting • Marketing • Logistics

Wing Assistant is a company specializing in providing virtual assistant services to businesses worldwide. The company offers a wide range of services including general virtual assistant work, executive assistance, customer service, bookkeeping, and digital marketing. Wing Assistant aims to enhance productivity for startups and enterprise teams by delegating tasks to dedicated virtual assistants, reducing operational load, and enabling businesses to focus on core activities. Their services are accessible via a subscription model, providing flexible and cost-effective solutions compared to traditional hiring methods. Clients benefit from a dedicated assistant model where the assistant works solely for their business, gaining a deeper understanding of their processes over time.

📋 Description

• 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 address 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 Sales Associate–Account Executive pairing • Establish cadence standards, ownership rules, and CRM hygiene expectations • Manage the Sales Trainer and own onboarding and ramp-up for new sales hires • Design 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 • Oversee channel-partner leads and opportunities and track partner performance • Review recorded calls and demos, conduct calibration sessions, and coach Account Executives • Join live deals to support representatives in progressing opportunities • 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

🎯 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 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

🏖️ Benefits

• $125,000–$155,000 annual base salary • 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

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