Head of Sales

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.

The Role

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.

• Build the Sales Performance Toolkit

  • Create the sales assets the floor runs on: sequences, talk tracks, objection-handling guides, battle cards, and demo collateral from zero where nothing exists today

  • Identify gaps in the sales motion and build the tool, process, or content that closes them

  • Evaluate, implement, and get real leverage from AI-enabled sales tools, conversation intelligence, and automation

• Team Leadership

  • 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 all new sales hires

• Follow-Up and Mid-Funnel Conversion

  • Design, write, and A/B test follow-up sequences across email and chat

  • Use reply rate, re-engagement rate, and conversion as your 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, beginning with the weakest-performing stage

• Channel Partner Lead Management

  • Oversee the handling of leads and opportunities generated through channel partnerships

  • Establish clear ownership, follow-up, and reporting standards for partner-sourced opportunities

  • Track channel partner performance and evaluate its effectiveness as a source of new business

• 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 to ensure consistent scoring and coaching standards

  • Join live deals when a representative needs support moving an opportunity forward

• Knowledge and Compliance

  • Own the sales knowledge base as the company's single source of truth

  • Maintain the content that powers our AI sales chat assistant

  • Establish a regular review cadence so customer-facing information remains accurate and current

  • Ensure claims made by sales representatives and…