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Kiley Coffey,
Associate, Investor Relations

Kiley is an Investor Relations Associate who joined the WindSail team in January 2022.  Prior to joining WindSail, Kiley worked as a senior associate focusing on new business development in the wealth management group at BNY Mellon.  Prior to that, Kiley interned at UBS in their UHNW private wealth group.

Kiley received a B.A. from Trinity College in Hartford, CT.  She currently serves as co-chair of the Horizons for Homeless Children P.L.A.Y. Network Leadership Committee and lives in Boston, MA.


Ian Bowles
Michael Rand
Matthew O'Rourke
Andrew Chang
Team Overview


Jessica Hart

Ian Bowles

Michael Rand

Managing Director

Managing Director

Matthew O'Rourke


Andrew Chang

Vice President

Jessica Hart


Ian Bowles, Co-Founder & Managing Director

Ian is co-founder and Managing Director of WindSail Capital Group. He brings over 30 years of experience in the energy and environmental sectors. Prior to WindSail, he served as Massachusetts Secretary of Energy and Environmental Affairs, where he oversaw a landmark restructuring of utility and environmental regulation which included making MA a top ranked state in energy efficiency, renewable energy and greenhouse gas emissions reductions. He was also chairman of the MA Water Resources Authority and the founding chairman of the MA Clean Energy Center. Earlier in his career, he served on the National Security Council staff of President Bill Clinton and was a Vice President at Conservation International where he played a key role in creation of the four million acre Central Suriname Nature Reserve.

Ian is a board member at Longroad Energy and formerly a board member at the New England Clean Energy Council and the Museum of Science. He is an advisor to several other leading clean energy companies. Ian received his A.B. from Harvard College and a Masters degree from Oxford University. A native of Woods Hole, MA, he currently lives in Dover with his wife and two children.

Michael Rand, Co-Founder & Managing Director

Michael is co-founder and Managing Director of WindSail Capital Group. Michael brings to WindSail over 25 years of experience in private equity investing, structured finance and corporate finance. Prior to founding WindSail, Michael spent 11 years as a private equity professional, most recently as a Managing Director of GB Merchant Partners, a division of Gordon Brothers Group. Previously, Michael served as a Principal at Palladin Capital Group, a New York based middle market private equity firm. Prior to joining Palladin, Michael was a member of the Leveraged Finance/Merchant Banking Division of CIBC World Markets.

Michael received a B.S. from Georgetown University and an MBA from New York University's Stern School of Business. He currently serves as the Chairman of Coaching4Change and lives in Wellesley, MA with his wife and three children.

Jessica Hart, Principal


Jessica is a Principal who joined the WindSail team in 2018. Jessica oversees all financial, compliance, and administrative functions for the firm. Prior to joining WindSail, Jessica worked at Station Houston, an accelerator for early stage technology companies, where she led day to day operations. Prior to joining Station Houston, Jessica was Director of Business Development and Marketing at Main Street Capital, where she led deal sourcing and marketing efforts for the lower middle market investment group. Prior to joining Main Street Capital, Jessica was Vice President of Finance and Administration for Clarium Capital Management, a San Francisco based hedge fund. Previously, Jessica was a staff accountant at Spencer Capital Management, a New York based hedge fund.

Jessica received a B.S. from the University of Montana and an MBA from
the McCombs School of Business at the University of Texas. She
currently lives in Concord, MA with her husband and two children.

Matthew O'Rourke, Managing Director

Matt is a Principal who joined the WindSail team in 2015.  Matt has over 10 years of broad industry experience as an investor and lender and has directly managed over $450 million in assets.  Prior to joining WindSail, Matt was a Vice President, Senior Portfolio Manager and founding team member at Salus Capital Partners, a $1.4-billion credit fund.  At Salus, Matt was responsible for underwriting, structuring and managing a diverse portfolio of credit facilities to lower middle market businesses across the U.S. and Canada.  Prior to joining Salus Capital, Matt was an Assistant Vice President at People’s United Bank, a $44-billion commercial bank where he sourced, underwrote and managed a portfolio of middle market commercial loans. Matt began his career at People’s United Bank as a credit analyst where he underwent an eighteen-month credit training and rotational program within the bank.


Matt is an active member of the startup community and is also involved in various trade organizations. Matt received a B.S. in Business Administration cum laude from Bryant University. He currently lives in Newton, MA with his wife and two children.

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Andrew Chang, Vice President

Andrew is a Vice President who joined the WindSail team in January 2021. Prior to joining WindSail, Andrew worked as an analyst in M&A advisory with King & Spalding and in investment banking with Wells Fargo Securities. Prior to that, Andrew spent a summer analyst term with the Debt Capital Markets group at Wells Fargo Securities.

Andrew received a B.A. from Amherst College. He currently lives in Boston, MA.

Kiley Coffey
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