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David Ainsworth

@davidainsworth

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I’m an executive insurance sales leader building trusted benefits solutions.

United States

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What I'm looking for

I want a role where I can help people through insurance solutions, lead enterprise partner growth (especially PEO channels), and use operations and training to build a trusted reputation—while owning strategy, negotiation, and measurable outcomes.

For the better part of 20 years, I’ve used insurance through an expansive network of brokers, carriers, PEOs, and relationships to help people get the protections they need. My goal is to find solutions that deliver real coverage value while helping the company build a trusted reputation.

As Vice President Enterprise Sales at Decisely, I manage large-scale enterprise relationships, develop go-to-market strategy involving PEOs, and handle contract negotiation for new PEO partners—overseeing 300% growth in assigned portfolios. Previously at Zynergia Insurance Agency, I helped build a new group healthcare benefits program from scratch (Taft Hartley Act), wrote $4.4M in new business premium in 2023 with 100% renewal, and drove 2024 forward on pace for $8M, while owning agency operations and training.

I’ve also led teams and operations across the insurance lifecycle, including 60% sales growth and 25% reduction in lost clients at Parks Insurance, and COO leadership at Phoenix Captive Solutions where I served as an authorized Captive Manager designated by the state of North Carolina. I’m a recognized subject matter expert in group insurance strategy and education, and I bring hands-on operational rigor through carrier relationships, training, and measurable KPI accountability.

Experience

Work history, roles, and key accomplishments

Vice President Enterprise Sales

Decisely

Jul 2024 - Feb 2026 (1 year 7 months)

Managed enterprise relationships to bring on new clients under enterprise umbrellas and developed go-to-market strategy for PEOs. Drove 300% growth in assigned portfolios and led contract negotiations for new PEO partners.

Enterprise Sales Strategic Partnerships Contract Negotiation Cross Division Strategy Microsoft Office ChatGpt

Vice President Operations

Zynergia Insurance Agency

Jan 2022 - Jun 2024 (2 years 5 months)

Built a new group healthcare benefits program from scratch under the Taft Hartley Act, including marketing and training for broker and PEO partners. Led agency operations and contract negotiations while producing $4.4M in new business premium in 2023 with 100% renewal and $8M in new business premium on pace for 2024.

Group Benefits Administration Taft Hartley Compliance Agency Operations Contract Negotiation Carrier Appointments Insurance Licensing

Senior Official

Kirwan Sports

Dec 1993 - Apr 2022 (28 years 4 months)

Officiated and regulated adult softball and recreation leagues, maintaining a safe and fair environment. Managed game play and de-escalation while keeping positive interactions with coaches, players, and parents.

Sports Officiating Conflict Resolution Coaching Coordination Game Administration

Director of Personal Lines

Parks Insurance

Nov 2019 - Jun 2020 (7 months)

Oversaw Personal Lines departments (service, sales, retention), achieving 60% sales growth and reducing lost clients by 25%. Implemented a new agency management system, improved activity tracking, and created cross-sell campaigns while managing carrier relationships and agency appointments.

Personal Lines Insurance Client Retention Sales Leadership Service Operations Agency Management Systems Process Improvement KPI Tracking Carrier Appointments Cross Sell

Chief Operating Officer

Phoenix Captive Solutions

Sep 2017 - Nov 2019 (2 years 2 months)

Served as Principal Broker and oversaw brokerage operations and regulatory processes for captive insurance formation and Workers’ Compensation solutions, designated by North Carolina as an authorized Captive Manager. Managed carrier, regulator, and client relationships and supervised brokerage personnel including hiring.

Captive Insurance Workers’ Compensation Regulatory Compliance Captive Management Brokerage Operations Carrier Relationship Management Client Relationship Management Process Development

Director of Broker Solutions

iSolvedOne

Aug 2016 - Jan 2017 (5 months)

Defined and developed Health and Welfare brokerage operations products, including sales training and talk tracks to support value-added HCM and brokerage services. Built and implemented workflow/process systems aligned to industry standards, and wrote functional product requirements with supporting materials for new releases.

Product Development Health And Welfare Brokerage Operations Sales Enablement Workflow Design Stakeholder Management And Training Materials

Sales Manager

TriNet HR Corporation

Nov 2008 - Jul 2016 (7 years 8 months)

Led a national PEO insurance brokerage focused on acquiring and retaining PEO clients, growing agency performance by 20% annually for five consecutive years. Increased PEO client retention by an average of 50% (with an additional 1 year tenure) and trained sales and client service teams on ancillary benefits positioning.

PEO Sales Client Retention Ancillary Benefits Positioning Carrier Relationship Management Premium Remittance

Insurance Agent

AAA

Mar 2006 - Nov 2008 (2 years 8 months)

Wrote $660,000 in premium over 28 months, averaging $24,000/month in new business as a solo Property & Casualty agent. Earned the AAA “App A Day” award and qualified for a Mexico company trip for two consecutive years.

Property & Casualty Sales Life Insurance Sales Commercial Insurance New Business Development Solo Agent Performance Client Acquisition