Head of Sales Performance
At Wing Assistant · United States
Salary: US$125,000–155,000 a year
- Sales
- Full-time
- Director or above
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Where you can work from
Open to the United States
“United States”
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- Posted
- 18 August 2026
- First seen by us
- 7 October 2026
- Last checked
- 26 hours ago
Job description
From Wing Assistant’s job post, as they wrote it.
What You'll Own
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
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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 automated channels 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
* 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
Preferred
* 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
Benefits & Compensation
$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
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