About The Cook Group The Cook Group is a growth-focused life insurance and financial services organization committed to protecting families, developing high-performing insurance professionals, and creating pathways to income, business ownership, wealth, and generational impact. We believe life insurance is more than a financial product. It is a critical tool for protecting income, preserving wealth, creating financial security, and building stronger financial legacies for families and communities. Our commitment extends equally to the agents who serve those families. The Cook Group provides insurance professionals with the training, coaching, technology, carrier access, sales systems, lead-generation resources, accountability, leadership development, and business infrastructure needed to build productive and sustainable insurance businesses. We are building more than an insurance agency. Our long-term vision is to develop The Cook Group into a premier wealth-building institution with an ecosystem of companies, services, technology, education, and opportunities designed to help families and professionals build, protect, and transfer wealth. Position Overview As we scale, we are making significant investments in the infrastructure behind agent success—including standardized onboarding, licensing and contracting support, CRM and automation, sales training, lead generation, performance management, leadership development, recruiting systems, accountability, recognition, and agent retention. Our culture is built around performance, development, accountability, service, innovation, and continuous improvement. Expectations should be clear. Performance should be measurable. Problems should be identified early. Support should be intentional. Success should be repeatable. Our goal is to create an organization in which every agent understands where they are, what is expected of them, what they must accomplish next, what resources are available to help them succeed, and what pathway exists for their continued growth. The Director of Agent Success & Performance will play a critical role in building the infrastructure behind agent success at The Cook Group. This person will help create an environment where every agent understands where they are, what they need to accomplish next, what resources are available to them, and what success looks like. The Cook Group is seeking a highly organized, results-driven Director of Agent Success & Performance to lead the agent journey from initial onboarding through activation, consistent production, professional development, and long-term retention. Ultimately, this role is responsible for turning agent development from a collection of individual activities into a measurable, accountable, repeatable system for building successful and sustainable insurance businesses that move agents through five critical stages: ONBOARD →
ACTIVATE
→ PRODUCE → DEVELOP → RETAIN This is a performance leadership role with direct responsibility for improving agent activation, productivity, development, engagement, and retention. The successful candidate will combine strong people skills with a highly analytical, systems-oriented approach. They will use data and performance indicators to identify where agents are getting stuck, diagnose the underlying cause, and implement the appropriate intervention. Core Responsibilities 1. Agent Onboarding Lead new-agent orientation and manage a structured onboarding process aligned with company culture, systems, and expectations. Partner with contracting teams to ensure agents become sales-ready with full access to CRM, carrier tools, scripts, and platforms. Track new agent milestones to ensure accountability of expectations and success metrics. Maintain the Agent Onboarding Tracker to provide leadership with clear visibility into onboarding completion rates. : Identify lagging agents early and initiate prompt support to keep them on schedule. 2. New Agent Activation Build and execute targeted activation plans to swiftly transition agents from onboarding to active production. : Track core metrics, including prospecting, appointment-setting, training attendance, and time to first issued/paid policy. : Intervene with low-activity agents by removing production barriers and coordinating targeted coaching or role-play sessions. : Reduce drop-off rates between initial licensing/contracting and consistent, active production. : Celebrate initial production wins, including first submitted applications and first issued policies. 3.
Agent Success & Performance Management :
Coach activated agents on the daily workflows, sales disciplines, and skills needed for long-term consistency. Regularly review production volume, conversion rates, and activity metrics to spot growth opportunities. Conduct regular 1-on-1 check-ins and performance reviews to maintain production standards. Provide advanced sales training, strategy sessions, and resource updates to elevate top-tier and developing producers. 4. Sales Skill Development Partner with leadership and training teams to pinpoint and elevate core skills that drive agent production. : Coach agents on prospecting, lead handling, appointment setting, pipeline tracking, follow-ups, and referral generation. : Build agent confidence in needs analysis, life insurance presentations, product knowledge, underwriting fundamentals, objection handling, and closing. : Train agents on essential business planning, time management, and recruiting practices. : Use real activity and production data to identify specific skill gaps instead of relying solely on generic training programs. 5. Agent Retention & Reactivation Identify disengagement risks by monitoring activity and production trends to conduct proactive retention outreach. Diagnose underlying struggles causing agents to slow down or disengage. Re-engage previously productive agents by developing individualized plans with targeted resources, leads, coaching, and accountability. Conduct exit interviews to uncover recurring organizational issues contributing to turnover. Regularly communicate retention trends and improvement opportunities to executive leadership. Maintain visibility into the agent population and assign the right support and accountability. Key Performance Indicators Own an executive-level Agent Success & Performance Dashboard and report regularly on agent-organization health.
Key metrics may include:
Onboarding & Ramp Speed:
Track onboarding completion rates, time-to-complete, milestone progress, and speed to first appointment, application, and issued/paid policy.
Production Volume & Premium:
Measure submitted and issued/paid annual premium, total applications, average production per agent, and counts of $5K+ and $10K+ monthly producers.
Conversion & Quality Metrics:
Monitor lead-to-appointment conversion, appointment-to-application conversion, policy placement, and persistency rates.
Retention & Engagement:
Track active producer percentages, retention rates, reactivation success, and performance improvement rates.
Participation & Dashboards:
Oversee the executive-level dashboard tracking agent-organization health, coaching attendance, and training participation. Translate metrics into insights on agent loss, production constraints, and highest-impact interventions. Requirements 8+ years onboarding, coaching, managing, or developing sales professionals. 3+ years managing a team or program. 5+ years of direct sales experience preferred. Bachelor's degree in HR or training and development preferred. Highly organized, proactive, and systems-oriented. Comfortable with data, dashboards, KPIs, and performance metrics. Strong coaching, communication, and leadership skills. Able to drive accountability while building trust. Proactively supports struggling agents. Builds repeatable processes and scalable systems. Understands sales funnels, pipelines, activity metrics, conversion rates, and production metrics. Comfortable managing agents at varied development stages. Strong judgment and performance-diagnosis skills. Life insurance, financial services, direct sales, or performance-driven sales experience preferred. Demonstrates professionalism, integrity, urgency, ownership, and clear communication.