Head of Sales Performance

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

📋 Description

• Develop sales assets such as sequences, talk tracks, objection-handling guides, battle cards, and demo materials.

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

• Assess and implement AI-driven sales tools, conversation intelligence, and automation strategies.

• Oversee and nurture the inbound follow-up team, which includes SDRs and Sales Associates.

• Conduct one-on-one meetings, provide performance coaching, hire as the team expands, and manage the Sales Associate–Account Executive pairing model.

• Set cadence standards, ownership guidelines, and expectations for CRM hygiene.

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

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

• Monitor reply rates, re-engagement rates, conversion rates, show rates, and funnel drop-off metrics.

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

• Manage channel-partner leads and opportunities, including ownership, follow-up, reporting, and performance assessment.

• Review recorded calls and demos using a structured sales scorecard and ensure monthly call-review coverage.

• Coach Account Executives and participate in live deals when support is necessary.

• Conduct calibration sessions to ensure consistent scoring and coaching standards.

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

• Ensure that customer-facing information is accurate, up-to-date, compliant, and aligned with sales claims.

⛳️ Requirements

• Minimum of 4 years of 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 constructing sales systems, tools, or programs from the ground up.

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

• Strong grasp of inbound sales funnels, lead management, and mid-funnel conversion strategies.

• Experience in coaching sales representatives on discovery, objection handling, urgency, and deal progression.

• Capability to review sales calls, pinpoint performance deficiencies, and provide actionable feedback.

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

• Strong CRM discipline with experience in platforms like HubSpot or Salesforce.

• Ability to utilize data for diagnosing funnel issues, setting targets, and managing performance.

• Excellent written and verbal communication skills in English.

• Willingness and ability to work during Pacific Time hours.

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

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

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

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

• Preferred: background in creating sales collateral, playbooks, or enablement content.

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

• Preferred: experience managing channel-partner leads.

• Preferred: knowledge of compliance, sales claims management, and customer-facing knowledge bases.

🏝️ 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 coverage.

• Company-sponsored team events and offsite activities.

• Clear pathways for career growth and expanded leadership roles.