Life Insurance Head Of Sales Jobs (NOW HIRING)

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.

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

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

$125,000 - $155,000 a year

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

What Success Looks Like

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.