The "REAL" Insurance Lady (T.R.I.L.)
Overview
Lead the Next Era of National, Community-Driven Sales Expansion The Real Insurance Lady (TRIL) is expanding nationwide and seeks a transformational Sales Director to lead one of the fastest-growing mission-driven sales organizations in the country. This is a strategic, data-driven, multi-channel sales leadership role responsible for building and scaling high-volume sales engines across call centers, field teams, commercial accounts, and community-based environments. About TRIL TRIL began as a small, family-run business and has grown into a nationally recognized movement dedicated to increasing access to essential coverage and financial protection solutions. Our work serves individuals, families, small businesses, churches, nonprofits, and community organizations nationwide. Our mission is rooted in empowerment, education, access, and equity. We work through: Grassroots outreach and community engagement Inbound and outbound call centers Field-based sales teams B2B and institutional partnerships Multi-product offerings such as health coverage navigation, life & supplemental products, financial protection solutions, and more TRIL is expanding rapidly and is building a leadership team committed to innovation, performance excellence, scalable systems, and community impact.
The Opportunity
The Sales Director is the strategic architect of TRIL’s national, multi-channel sales operation. In this role, you will: Lead a high-performing national sales force across call centers, field teams, and community outreach teams Design and execute TRIL’s multi-channel revenue strategy Expand TRIL into new markets, customer segments, and institutional channels Drive consistent, year-round growth across diverse product lines Build scalable systems, processes, and sales infrastructure that support national expansion Strengthen TRIL’s reputation as the most trusted community-centered sales organization in the country This is a hands-on, results-driven leadership role suited for a Sales Director who thrives in high-growth, purpose-centered environments.
What You Will Do
As TRIL’s Sales Director, you will: Oversee sales across grassroots outreach, call centers, community events, commercial accounts, and partner organizations Build strategies for B2C, B2B, and institutional client acquisition Expand TRIL into new markets, industries, and communities
Build & Scale a High-Performing Sales Organization
Recruit, train, and develop junior and senior sales agents, team leads, and managers Build a professionalized training & development pipeline
Drive Revenue, Forecasting & Market Expansion
Lead forecasting, analytics, and performance modeling Ensure year-round revenue growth across multiple product categories Identify emerging opportunities and create scalable growth strategies
Ensure Exceptional Customer Experience & Retention
Standardize communication quality and client engagement practices Strengthen retention strategies and multi-product relationships Partner with operations and retention teams to improve the customer journey
Build Scalable Sales Systems & Infrastructure
Implement CRM discipline, reporting dashboards, and KPI tracking Build SOPs, workflows, and sales scripts across all channels Improve efficiency, automation, and data accuracy
Develop Strategic Partnerships
Cultivate relationships with businesses, churches, ministries, health systems, nonprofits, schools, and community organizations Collaborate with Marketing, HR, Operations, Retention, and Technology to align organizational goals Represent Sales in strategic planning and cross-functional initiatives
What Success Looks Like
Achieving ≥110% of annual revenue targets Sustained YoY customer growth of 10%+ High agent retention (≥90%) and strong performance culture Expansion into new markets, industries, and customer segments Improved retention, CSAT, NPS, and service consistency Scalable systems, documented SOPs, and forecast accuracy ≥95% Strong community partnerships and expanded organizational reach Transition of TRIL from a grassroots business into a structured, scalable national enterprise
Who We’re Looking For
A seasoned Sales Director with experience leading large, complex, multi-channel sales environments, such as: Grassroots community sales Inbound/outbound call centers B2B and institutional sales Consumer sales at scale Multi-product or multi-line sales organizations
Qualifications
Required: 7–12 years of progressive leadership in multi-channel or multi-product sales Experience managing community/outreach sales + call centers + field teams Proven ability to hit and exceed aggressive revenue targets Experience leading teams of 20–100+ sales professionals Background in high-volume B2C and/or B2B client acquisition Strong competency in CRM oversight, analytics, and forecasting Ability to build scalable systems and sales structures Experience working with diverse communities and mission-driven environments Preferred: Experience in healthcare, financial services, or protection-product industries Experience with employer sales, institutional partnerships, or benefits-related products Experience modernizing a growing organization or leading through scale Background in grassroots or community-focused organizations
How to Apply
Please submit: Resume A brief leadership statement describing your multi-channel sales experience and interest in the role Send to: DesireeK@therealinsurancelady.com Join TRIL. Lead the next era of community-centered national growth. If you're ready to build a national sales engine, lead diverse teams, and strengthen access for communities across America—we want to hear from you. Seniority level Director Employment type Full-time Job function Sales and Business Development Industries Insurance Note: This description consolidates the core responsibilities, qualifications, and application details for the Sales Director role and omits extraneous postings and site-specific UI elements.
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Lead the Next Era of National, Community-Driven Sales Expansion The Real Insurance Lady (TRIL) is expanding nationwide and seeks a transformational Sales Director to lead one of the fastest-growing mission-driven sales organizations in the country. This is a strategic, data-driven, multi-channel sales leadership role responsible for building and scaling high-volume sales engines across call centers, field teams, commercial accounts, and community-based environments. About TRIL TRIL began as a small, family-run business and has grown into a nationally recognized movement dedicated to increasing access to essential coverage and financial protection solutions. Our work serves individuals, families, small businesses, churches, nonprofits, and community organizations nationwide. Our mission is rooted in empowerment, education, access, and equity. We work through: Grassroots outreach and community engagement Inbound and outbound call centers Field-based sales teams B2B and institutional partnerships Multi-product offerings such as health coverage navigation, life & supplemental products, financial protection solutions, and more TRIL is expanding rapidly and is building a leadership team committed to innovation, performance excellence, scalable systems, and community impact.
The Opportunity
The Sales Director is the strategic architect of TRIL’s national, multi-channel sales operation. In this role, you will: Lead a high-performing national sales force across call centers, field teams, and community outreach teams Design and execute TRIL’s multi-channel revenue strategy Expand TRIL into new markets, customer segments, and institutional channels Drive consistent, year-round growth across diverse product lines Build scalable systems, processes, and sales infrastructure that support national expansion Strengthen TRIL’s reputation as the most trusted community-centered sales organization in the country This is a hands-on, results-driven leadership role suited for a Sales Director who thrives in high-growth, purpose-centered environments.
What You Will Do
As TRIL’s Sales Director, you will: Oversee sales across grassroots outreach, call centers, community events, commercial accounts, and partner organizations Build strategies for B2C, B2B, and institutional client acquisition Expand TRIL into new markets, industries, and communities
Build & Scale a High-Performing Sales Organization
Recruit, train, and develop junior and senior sales agents, team leads, and managers Build a professionalized training & development pipeline
Drive Revenue, Forecasting & Market Expansion
Lead forecasting, analytics, and performance modeling Ensure year-round revenue growth across multiple product categories Identify emerging opportunities and create scalable growth strategies
Ensure Exceptional Customer Experience & Retention
Standardize communication quality and client engagement practices Strengthen retention strategies and multi-product relationships Partner with operations and retention teams to improve the customer journey
Build Scalable Sales Systems & Infrastructure
Implement CRM discipline, reporting dashboards, and KPI tracking Build SOPs, workflows, and sales scripts across all channels Improve efficiency, automation, and data accuracy
Develop Strategic Partnerships
Cultivate relationships with businesses, churches, ministries, health systems, nonprofits, schools, and community organizations Collaborate with Marketing, HR, Operations, Retention, and Technology to align organizational goals Represent Sales in strategic planning and cross-functional initiatives
What Success Looks Like
Achieving ≥110% of annual revenue targets Sustained YoY customer growth of 10%+ High agent retention (≥90%) and strong performance culture Expansion into new markets, industries, and customer segments Improved retention, CSAT, NPS, and service consistency Scalable systems, documented SOPs, and forecast accuracy ≥95% Strong community partnerships and expanded organizational reach Transition of TRIL from a grassroots business into a structured, scalable national enterprise
Who We’re Looking For
A seasoned Sales Director with experience leading large, complex, multi-channel sales environments, such as: Grassroots community sales Inbound/outbound call centers B2B and institutional sales Consumer sales at scale Multi-product or multi-line sales organizations
Qualifications
Required: 7–12 years of progressive leadership in multi-channel or multi-product sales Experience managing community/outreach sales + call centers + field teams Proven ability to hit and exceed aggressive revenue targets Experience leading teams of 20–100+ sales professionals Background in high-volume B2C and/or B2B client acquisition Strong competency in CRM oversight, analytics, and forecasting Ability to build scalable systems and sales structures Experience working with diverse communities and mission-driven environments Preferred: Experience in healthcare, financial services, or protection-product industries Experience with employer sales, institutional partnerships, or benefits-related products Experience modernizing a growing organization or leading through scale Background in grassroots or community-focused organizations
How to Apply
Please submit: Resume A brief leadership statement describing your multi-channel sales experience and interest in the role Send to: DesireeK@therealinsurancelady.com Join TRIL. Lead the next era of community-centered national growth. If you're ready to build a national sales engine, lead diverse teams, and strengthen access for communities across America—we want to hear from you. Seniority level Director Employment type Full-time Job function Sales and Business Development Industries Insurance Note: This description consolidates the core responsibilities, qualifications, and application details for the Sales Director role and omits extraneous postings and site-specific UI elements.
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