Head of Sales Performance

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Wing Assistant

WebsiteLinkedInAll Job Openings

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 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 onboarding and ramp-up for new sales hires • Establish cadence standards, ownership rules, CRM hygiene expectations, and the pairing model between Sales Associates and Account Executives • Design, write, and A/B test follow-up sequences across email and chat • Manage no-show recovery, rebooking, and reactivation campaigns for aged and closed-lost opportunities • Reduce stage-to-stage funnel drop-off and improve mid-funnel conversion • 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 claims and automated-channel information are accurate and compliant • Raise sales-floor quality through coaching, performance management, process improvement, and sales technology

🎯 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 • 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 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

• $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