Head of Sales Performance

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

📋 Description

• Develop sales resources that include sequences, conversation frameworks, objection-handling manuals, battle cards, and demonstration materials.

• Identify shortcomings in the sales process and create tools, procedures, or content to address them.

• Assess and integrate AI-driven sales tools, conversation analytics, and automation solutions.

• Oversee and cultivate the inbound follow-up team, which comprises SDRs and Sales Associates.

• Conduct regular one-on-one meetings, coach team performance, and hire as the team grows.

• Manage the pairing system between Sales Associates and Account Executives.

• Set standards for cadence, define ownership rules, and maintain CRM hygiene expectations.

• Supervise the Sales Trainer and take charge of the onboarding and ramp-up processes for new sales personnel.

• Create, compose, and A/B test follow-up sequences across email and chat platforms.

• Handle no-show recovery, rebooking, and reactivation initiatives.

• Minimize drop-off rates at each stage of the sales funnel.

• Oversee channel-partner leads and opportunities, including responsibility for ownership, follow-up, reporting, and performance tracking.

• Review recorded calls and demonstrations using a standardized sales scorecard.

• 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.

• Manage the sales knowledge base and content that powers the AI sales chat assistant.

• Ensure that all customer-facing sales information and claims are accurate and compliant.

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

⛳️ Requirements

• A minimum of 4 years of experience in inside sales, sales development, sales enablement, revenue operations, or a related commercial role.

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

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

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

• Deep 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 analyze sales calls, pinpoint performance gaps, and deliver clear, actionable feedback.

• Practical experience in developing sales sequences for email, chat, SMS, or other follow-up channels.

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

• Comfortable utilizing data to identify funnel issues, establish targets, and manage performance.

• Excellent written and verbal communication skills in English.

• Willingness and capability to work during Pacific Time hours.

• Preferred: experience managing SDRs or Sales Associates and Account Executives.

• Preferred: experience in overseeing sales onboarding, training, and representative ramp-up programs.

• Preferred: experience in developing no-show recovery, closed-lost reactivation, or aged-pipeline campaigns.

• Preferred: familiarity with AI-driven sales tools, conversation analytics, and sales automation platforms.

• Preferred: experience in creating sales collateral, playbooks, or enablement content that is widely adopted.

• Preferred: experience in a high-growth startup, SaaS, staffing, outsourcing, or technology-enabled services company.

• Preferred: experience managing leads generated through channel partnerships.

• Preferred: understanding of compliance, management of sales claims, and maintaining a customer-facing knowledge base.

🏝️ Benefits

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

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

• Paid Time Off (PTO).

• Paid U.S. holidays.

• Paid sick leave.

• Health insurance.

• Company-sponsored team events and offsite gatherings.

• Clear pathways for career advancement and increased leadership responsibilities.