Head of Sales Performance

United StatesRemoteFull Timeexecutive

OtherSales Performance

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Quick Summary

Overview

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,

Technical Tools

OtherSales Performance

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.

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

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

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

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

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

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 automated channels are accurate and compliant

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 not just running ones that already existed
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 Have

~1 min read

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

You are a strong fit for this role if you are a hands-on operator and a force multiplier someone who makes the people and systems around them better, not just their own numbers.

You should be comfortable moving between strategy and execution: reviewing a dashboard in the morning, rewriting a follow-up sequence at noon, coaching an underperforming representative in the afternoon, and helping an Account Executive move a difficult deal forward before the day ends. When something the team needs doesn't exist, your instinct is to build it.