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The Deft Team

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The Deft Team

Deft Claims was formed in early 2018 from the mindset of creating a solution to the near gridlocked claims dispute resolution process in the aftermath of Hurricane Irma. Jeremiah and his team recognized that there is a more efficient way to handle complex claims. One which gives some leverage back to the carrier while at the same time fulfilling the carrier’s promise to those they insure as our mission reflects.

Jeremiah Kiefer

President | Executive General Adjuster

After stints in academia and general contracting, Jeremiah entered the claims handling arena during the chaotic 2005 hurricane season. He quickly found in claims handling a perfect match for his core skill set and enjoyed the freedom to excel independently. Having handled nearly 10,000 assignments across much of the property claims spectrum over his 16-year career as independent field adjuster, his ambitions broadened in 2017 which led to his founding Deft Claims. By the end of 2018, Deft Consultants and Deft Tech were added to round out The Deft Group’s triumvirate.

Beyond his ownership role, Jeremiah continues to lead The Deft Group from the front. In addition to overseeing operations and administration, he personally handles the most complex of assignments in the capacity of Executive General Adjuster or Lead Consultant. With one eye always on the future, and alongside Deft’s ever-expanding team, Jeremiah embraces the role of a pioneer mapping a course to the next generation of claims handling.


Jessica Weko

VP of Administration

After earning a Bachelor of Science in Hospitality and Tourism Management from Purdue University and managing high volume restaurants for 13 years, 7 of which as a General Manager overseeing $6.5 million in sales, Jessica sought out a new challenge in a new industry.  This search led her to The Deft Group and its companies.  Since joining The Deft Group in early 2018, Jessica has found an outlet for her entrepreneurial spirit while being a crucial part of Deft’s overall business development by implement processes and procedures.  Her ambitions and abilities as Deft’s business manager have led to her recent promotion to Vice President of Administration.  The value Jessica adds to Deft Claims and its sister companies cannot be over-stated.

Matthew Overstreet

Senior General Adjuster | Consultant | Umpire-Appraiser

Matthew started his insurance career in 2011 with Allstate’s National Catastrophe Team as a property claims adjuster. He immediately distinguished himself and rose quickly through the ranks. Over the 6 years which followed, he held many roles at Allstate including Vendor Oversight, Catastrophe Team Lead, National Catastrophe Team Trainer, Quality Develop Technician and Claim Service Leader.

In 2017 Matthew saw the opportunity to open his own business, drawing from the skills he gained at Allstate to again distinguish himself from his peers as an independent General Adjuster. He excelled in the commercial and high net worth claims handling space which brought he and other members of The Deft Team together. This alignment eventually led to Matthew joining forces with Deft Claims where he currently occupies the seat of “Senior General Adjuster".

Michael Dillon Boleware

General Adjuster

Dillon started his insurance career in 2011 with Quick Cat Claims where he assisted the president and claims manager with daily tasks such as adjuster relations, claim intake and roster management. He shortly thereafter, and with the help of his mentors, carved out his own place in the industry handling daily property and liability claims for several independent adjusting firms. In 2015 Dillon took on a position with York managing and training adjusters nationwide.

After nearly a decade of well-balanced industry experience, Dillon joined the Deft team in 2019 in the capacity of General Adjuster and with the ambition of becoming its Claims Manager. He has since embraced the opportunity to be a key facilitator for the rapid growth of Deft and has solidified his position as the leader of its claims division. Dillon stands alongside our executive team as we innovate how commercial and high net worth claims are handled in an environment where adaptation and break-neck speed is paramount.

Stephen Medeiros

General Adjuster | Consultant | Umpire-Appraiser

While working across a wide spectrum of the claims handling arena, Stephen’s passion has been and remains dispute resolution. Early on in his 16-year career, he found himself in a position to develop the appraisal procedures for a major US property carrier. This experience, and a dedication to continually expanding his knowledge base and credentials, has allowed Stephen to flourish in the appraisal and mediation space and leave him well positioned to be a leader in dispute resolution for decades to come.

Stephen joined the Deft Team in 2019 after being approached by its executive team to lead it Appraisal Division. His and Deft’s ambitions and motivations aligned to an extent where a union between his Texas and Florida centric appraisal network and Deft’s growing national brand quickly surfaced as an inevitability.

Darin Bradley

General Adjuster | Technology Specialist

Darin began his professional career working with Apple’s iOS division and Intuit’s TurboTax division respectively. His strengths as a manager were quickly recognized by his seniors who in turn put him in charge of as many as 30 agents before the age of 23. His work on the Intuit account for Concentrix led to his taking on additional responsibilities as an instructor of as many as 30 recruits. Over the course of the following several years, Darin continued to develop serving as leader for Claremont Food’s production team, creating a new position for himself as a technical production lead, blending his strengths as a leader with his skills as a maintenance technician resulting in the doubling of the program’s production rates within his first week.

While pursuing a future in automotive management in 2017, Darin was presented an opportunity to handle property claims in the aftermath of Hurricane Irma. He made a very ambitious decision to pursue this opportunity which has served him well. Darin’s talents quickly showed during this first deployment catching the eye several in our industry working with and around him in the field. In early 2018 after deployments associated with Hurricane Irma had concluded, Jeremiah reached out to Darin to discuss his interest in joining the Deft team as a technology advisor and field adjuster. This union has proved beneficial to both parties as Darin continues to make himself an indispensable resource for The Deft Group. He is truly a jack of all trades.