Head of Sales Performance

Wing Assistant • New York, NY

5d • $125,000 - $155,000

About The Position

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.

We're looking for a Head of Sales Performance to build, own, and multiply the performance of our inbound sales engine from the first follow-up touch through close.

This is a builder's role, not a caretaker's. You won't be inheriting a finished machine; you'll be constructing one. That means creating the tools, sequences, collateral, coaching systems, and standards that make every rep on the floor measurably better and personally stepping into the work when needed.

You will lead the inbound follow-up function, strengthen the systems and processes behind it, coach the team, and ensure every qualified opportunity is managed with discipline and urgency. Beyond your direct team, you will raise the quality and consistency of how the entire sales floor sells through coaching, performance management, process improvement, and the thoughtful use of sales technology.

You will have a team, a modern sales tech stack, and clear revenue and performance targets tied directly to your ownership. As you establish the sales performance engine, your scope may expand into post-sale revenue onboarding, retention, and account expansion.

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

Nice To Haves

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

Responsibilities

• Build the Sales Performance Toolkit: Create sales assets like sequences, talk tracks, objection-handling guides, battle cards, and demo collateral. Identify gaps in the sales motion and build the necessary tools, processes, or content. Evaluate, implement, and leverage AI-enabled sales tools, conversation intelligence, and automation.
• Team Leadership: Manage and develop the inbound follow-up team (SDRs and Sales Associates), including hiring as the team scales. Conduct regular 1:1s and coach performance. 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.
• Follow-Up and Mid-Funnel Conversion: Design, write, and A/B test follow-up sequences across email and chat, using reply rate, re-engagement rate, and conversion as primary scorecards. Build and manage the no-show recovery motion for cancellations and missed demos. Turn missed and cancelled demos into rebooked conversations. Build and run reactivation campaigns for aged and closed-lost opportunities. Reduce stage-to-stage drop-off across the funnel.
• Channel Partner Lead Management: Oversee the handling of leads and opportunities generated through channel partnerships. Establish clear ownership, follow-up, and reporting standards. Track channel partner performance and evaluate its effectiveness.
• Sales Quality and Coaching: 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. Join live deals when a representative needs support.
• Knowledge and Compliance: 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.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed