Head of Sales Performance

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop sales materials such as sequences, conversation guides, objection-handling resources, battle cards, and demo collateral.

• Recognize deficiencies within the sales process and create tools, workflows, or content to address them.

• Assess and deploy AI-driven sales tools, conversation intelligence, and automation solutions.

• Lead and enhance the inbound follow-up team, including Sales Development Representatives (SDRs) and Sales Associates.

• Conduct one-on-one meetings, coach team performance, recruit as the team grows, and oversee the Sales Trainer.

• Manage the pairing model between Sales Associates and Account Executives, establish cadence standards, ownership guidelines, and ensure CRM cleanliness.

• Create, compose, and conduct A/B tests for email and chat follow-up sequences.

• Oversee no-show recovery, rebooking, reactivation, and campaigns for closed-lost opportunities.

• Minimize drop-off rates at each stage of the funnel by analyzing reply rates, re-engagement rates, and conversion metrics.

• Supervise channel-partner leads and opportunities, including management, follow-up, reporting, and performance assessment.

• Evaluate recorded calls and demos with a written sales scorecard, ensuring monthly review coverage is maintained.

• Mentor Account Executives on discovery techniques, objection handling, urgency, and securing follow-up calls.

• Facilitate calibration sessions and participate in live deals when representatives require assistance.

• Maintain the sales knowledge base and content that supports the AI sales chat assistant.

• Ensure accuracy and compliance of customer-facing sales claims and automated channel information.

• Build and lead Wing Assistant's inbound sales performance engine for its AI-enabled workforce solutions.

⛳️ Requirements

• Minimum of 4 years’ experience in inside sales, sales development, sales enablement, revenue operations, or a comparable commercial role.

• At least 2 years of experience in managing or coaching a sales team.

• Proven history of establishing sales systems, tools, or programs from the ground up.

• Demonstrated success in enhancing follow-up processes, pipeline conversion rates, show rates, or sales-cycle efficiency.

• Comprehensive understanding of inbound sales funnels, lead management, and mid-funnel conversion strategies.

• Experience in coaching sales representatives on discovery, objection handling, urgency, and advancing deals.

• Ability to review sales calls, pinpoint performance gaps, and deliver actionable feedback.

• Practical experience in creating sales sequences across various channels including email, chat, SMS, or other follow-up mediums.

• Strong CRM discipline and familiarity with platforms such as HubSpot or Salesforce.

• Proficiency in utilizing data to identify funnel issues, establish targets, and oversee performance.

• Excellent written and verbal communication skills in English.

• Willingness and capacity to work during Pacific Time hours.

🏝️ Benefits

• Annual base salary ranging from $125,000 to $155,000, depending on experience.

• Performance-based bonuses linked to individual and company objectives.

• Paid Time Off (PTO).

• Observance of paid U.S. holidays.

• Paid sick leave.

• Health insurance coverage.

• Company-sponsored team events and offsite gatherings.

• Clear pathways for career advancement and increased leadership roles.

• Flexible remote work arrangement.