Bold Penguin Welcomes Chief Financial Officer to Executive Team

Seasoned Financial Executive Dan Gifford Joins Bold Penguin as CFO


COLUMBUS,OHIO, Aug. 6, 2020 – Bold Penguin, a rapidly growing commercial insurance technology provider, today announces Dan Gifford as its chief financial officer. Gifford comes to Bold Penguin with 30 years of experience in both public and private companies such as KPMG, Nationwide, Progressive Medical and DASCO Home Medical Equipment and has led three successful ownership events.

“I couldn’t be more thrilled to welcome Dan to Bold Penguin. His wealth of knowledge and experience support our objectives to financially and strategically scale the business in a highly regulated and competitive environment,” said Ilya Bodner, founder and CEO of Bold Penguin. “As our organization grows, so does our executive leadership team, and it’s exciting to bring on high caliber, results-oriented professionals like Dan.”

Gifford now leads the financial operations, interfacing internally and with investor relations teams,and will report directly to Bodner. He will help lead Bold Penguin’s focus on forecasting, unit economics and long-range strategic initiatives. The company’s size has more than doubled year-over-year since inception, and in 2019 the business hit a milestone of 1 million small business quote experiences through its Exchange. This year, Bold Penguin projects it will more than double its size, all while maintaining a better gross margin and adding two more of the top 10 insurance P&C carriers as terminal users.

Gifford comes with background working for entrepreneurial organizations and comes to Bold Penguin from DASCO Home Medical Equipment, where he served as CFO. During his career, Gifford has also held a number of positions for public and private companies including leading the due diligence teams through several transactions. More specifically, he worked at KPMG auditing insurance and financial services companies, Nationwide Insurance where he was instrumental in a diligence process and while at Progressive Medical he led the organization through significant sales transactions. 

“Bold Penguin was a natural fit based on my resume and professional background, but I was really attracted to this role because of the team’s energy. Everyone I met with had such focus and drive, and I wanted to be part of it,” said Gifford. “I look forward to building out along-term forecast and bringing a dedicated focus to the CFO role. My experience taking private companies to the next level in terms of financial reporting and driving confidence with key stakeholders will help build on the existing solid foundation.”

He succeeds Seth Metcalf who will remain at Bold Penguin in the role as General Counsel. Metcalf joined Bold Penguin four years ago after serving as Deputy Treasurer for the State of Ohio.

About Bold Penguin

Bold Penguin is where technology enhances the human touch in commercial insurance.With a heavy focus on agents, Bold Penguin upgrades the user experience for businesses, creates an easy tool for agents, and offers a streamlined process of underwriting for carriers. Bold Penguin was founded in 2016 by a group of entrepreneurs who spent their early days working with Allstate, Nationwide and Progressive alongside regional carriers and established insurance agencies. For more details, please visit

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