Covered Insurance Solutions Expands Leadership Team

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CRO and COO Bring Revenue and Operational Scaling Experience as Covered Expands into Mortgage Servicing, Lending, and Real Estate Channels

Covered Insurance Solutions, Inc. (Covered), an independent digital insurance marketplace, is excited to announce the recent appointments of Robert S. Brennan as Chief Revenue Officer and Mickey Freeman as Chief Operating Officer. Brennan and Freeman join the leadership team at a crucial time, as the insurtech scaleup gains traction in providing a faster, simpler, and more personalized way to provide property and casualty insurance products to consumers.

Brennan previously joined Covered’s Advisory Board in June 2019. He has been instrumental in advising the company on its channel partner strategy and product development efforts. Prior to joining Covered as CRO, he served as EVP of Corporate Strategy & Business Development at mortgage servicer Specialized Loan Servicing (SLS), a subsidiary of Australian-based Computershare. At SLS, Brennan led sales teams and partnership efforts in developing and nurturing relationships with banks, hedge funds, private equity firms, independent mortgage banks, and asset managers. At Covered, Brennan will focus on strategic partnerships, cross-channel distribution, market development, and commercial marketing.

Freeman brings 25 years of general management, operations, and marketing experience in technology-driven companies, social enterprises, and national nonprofits. Prior to Covered, Mickey served as President and Co-Founder of Education Funding Partners, a leading social Certified Benefit Corporation and digital marketing company connecting consumer brands with public schools. He previously served as President of Outward Bound Wilderness, COO of Outward Bound USA, and President of Schoolpop, a market-making digital fundraising platform. A graduate of Harvard Business School, Freeman began his career at Sprint Corporation. At Covered, Freeman will focus on operations, strategy, corporate development, and omni-channel marketing.

The expansion of Covered’s leadership team mirrors the expansion of the company’s offerings. Covered now partners with leading mortgage lending, servicing, and real estate providers to offer integrated solutions that help streamline the process of home-buying and annual insurance renewal. Covered’s solutions are designed to help partners reduce inefficiency and strengthen relationships while driving value for the end consumer.

“As our business model grew from startup to scaleup, we sought executive sales and operations talent that has ‘been there, done that’,” said Covered Co-Founder and CEO Ross Diedrich. “Rob’s strategic partnership experience and ability to create win-win partnerships in the mortgage servicing and lending channels was immediately apparent. Mickey’s extensive multi-sector, enterprise-driven experience in rapid-growth environments is being applied to grow revenues and results without sacrificing quality and customer enthusiasm. We’re excited to see what 2019 will bring with our expanded leadership team.”

About Covered Insurance Solutions, Inc.
Covered is the smarter, easier, and faster way to buy homeowners insurance. We’re an independent, consumer-first insurance agency focused on making insurance easy to understand and painless to purchase. Our integrated online marketplace combines intuitive technology with a human touch to help consumers quote, compare, and purchase the right coverage at the best price in minutes. We partner with mortgage lending, servicing, and real estate providers to make the home-buying process seamless. Covered is innovating insurance: We’re a Housingwire 2018 HW Tech100™ winner and one of Kairos’ “50 World-Changing Startups to Watch in 2019.” Learn more at and follow us on Facebook, Twitter, and LinkedIn.

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Christopher Diedrich

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