Dylan Whitehead

Claims Quality Control Manager at Hippo Insurance

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Work experience

Mar 2021 - Present

Hippo Insurance

Claims Quality Control Manager


Nov 2019 - Present

Alloy Claims

Founder & Senior Advisor

Founded a technology focused Third Party Administrator for Property & Casualty claims. Built company from the ground up and managed all aspects of operations. Participated in conferences and spoke at industry events. Designed claims processes to support clients and their customers. Responsible for sales and marketing.

Mar 2020 - Mar 2021

Hallmark Financial Services Inc.

Claims Director

Led auto casualty group in non-standard PL auto across multiple states


May 2018 - Mar 2020


Head of Personal Lines Claims - Australia

Responsible for claims operations for all individual personal insurance in Australia & New Zealand. Lines included Auto, Homeowners, PCG (high net worth), & Recreational Marine. Managed direct/indirect reports, TPAs, MGAs, and other outsourced service providers. Oversaw heavy growth in a startup environment. Made decisions about claims processes and technology. Directed transition from legacy systems with a heavy reliance on manual process to a modern technology based claims environment leveraging latest insuretech processes and automation. Completed cost benefit analyses to quantify impact of proposed changes. Liaised with internal, external, and regulatory stakeholders and owned final decisions on complex coverage matters to include litigated cases. Worked within a high financial authority to independently adjudicate contested claims. Managed relationships with external broking partners. Attended and spoke at trade shows/conferences. Worked closely with client & broker engagement and appeared at industry events. Worked closely with heads of underwriting and actuarial and consulted on pricing, risk selection, and policy wordings. Collaborated regularly with operations, compliance, and IT functions to achieve business goals while meeting all stakeholder's needs.


Jan 2015 - May 2018


Claims QA Director - Global Consumer Property & Casualty Claims

Headed corporate claims audit program for Consumer Lines P&C programs globally, including Auto, Homeowners, Yacht/Boat, Plus programs, Casualty, and others. Managed on-site benchmark reviews in many countries as well as continuous file audit program. Managed process for both line of business manager Open File Reviews and independent Closed File Reviews completed by auditors reporting to me. Completed national level compliance reviews to ensure adherence to US/local regulatory requirements as well as AIG internal standards. Served as Subject Matter Expert for numerous technical projects. Headed innovation team to find process improvements and identified millions of dollars in savings for AIG. Worked closely with local and global line of business heads and global training heads to identify opportunities and drive performance. Consistently recognized as a top performer by members of my department as well as external stakeholders.


Sep 2016 - Sep 2017

The Dallas Morning News

Community Voices Columnist

Served as a writer for the Dallas Morning News op-ed section, specializing in writing on topics affecting day to day life in the North Texas community


Dec 2011 - Dec 2014

Progressive Insurance

Casualty Claims Manager

Managed claims adjusters responsible for investigating and adjudicating 3rd party bodily injury claims on behalf of personal lines and commercial lines insureds. Completed real-time claims reviews for intervention and quality assurance. Actively on-boarded and trained new adjusters. Conducted interviews and made hiring decisions for new employees as well as promotions. Worked with peers and managers on special projects and consulted on process improvements. Participated in pilot programs to improve efficiency and quality. Coordinated ongoing charitable effort for North Texas area.


Aug 2005 - Dec 2011

Progressive Insurance

Claims Adjuster

Bodily Injury Adjuster - Responsible for investigating, negotiating, and settling 3rd party bodily injury claims. Also responsible for adjudicating property damage claims, investigating coverage, liability, and fraud Commercial Auto Adjuster - Responsible for investigating and adjudicating claims involving commercial insureds. Identified potentially vicariously responsible parties in order to protect commercial customers. Investigated and interpreted complex commercial policy language Fire/Theft Adjuster - Responsible for investigating fire and theft claims. Completed in-person meetings and interviews with involved parties. Completed scene canvases. Conducted in-depth investigations to identify potentially suspicious factors and frauds. Inspected stolen/burned vehicles to identify physical evidence Property Damage Appraiser - Completed inspections of personal and commercial vehicles in order to assess and pay for property damage incurred. Negotiated with repair facilities to reach agreed price and repair times. Managed customer expectations and rental vehicles. Completed all supplemental estimates.

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