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Like a Boss from the Portland Press Herald

Portland Press Herald

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Like a Boss from the Portland Press Herald

Like a Boss from the Portland Press Herald

Portland Press Herald

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About Us

The Portland Press Herald presents, Like A Boss, the live Q&A business event series. Our CEO and Publisher, Lisa DeSisto, will meet one-on-one with local CEOs and business leaders for a behind the scenes look at their career paths, the ups and downs of running their businesses and the trends shaping them. Join us to hear insightful, first-hand accounts of the realities of running a business.

Latest Episodes

Like a Boss Now - Kristen Miale, President of Good Shepherd Food Bank

Like A Boss Now is a series of live webinar interviews where you can hear insightful, first-hand accounts of the realities of running a business. Portland Press Herald CEO and Publisher Lisa DeSisto will interview Maine CEOs for insights on how they are managing, adapting, and problem solving in these ever-changing times. As a lifelong advocate for ending food insecurity, Kristen Miale, president of Good Shepherd Food Bank, has worked tirelessly to grow organizational partnerships throughout the state of Maine. She and her team of 80 work with a network of more than 400 nonprofit organizations to distribute 25 million meals a year, making Good Shepherd Food Bank Maine’s largest hunger relief organization.

38 minAPR 25
Comments
Like a Boss Now - Kristen Miale, President of Good Shepherd Food Bank

Like a Boss: Tony Shurman - President and CEO of Jasper Wyman & Son

Portland Press Herald Publisher and CEO Lisa DeSisto interviews Tony Shurman at the Portland House of Music in Portland Maine on February 28, 2020. Shurman is President and CEO of Jasper Wyman & Son (“Wyman’s”) the second largest brand in the retail frozen fruit category in the U.S. with its most notable product being wild blueberries. Founded in 1874, Wyman’s is a family-owned business headquartered in Down East Maine with an ongoing commitment to environmental stewardship, corporate social responsibility and product innovation. Prior to joining Wyman’s in 2017, Tony ran the Post Foods breakfast cereal business which includes brands such as Honey Bunches of Oats, Grape Nuts, Pebbles, and Post Shredded Wheat. Earlier in his career he worked in brand management roles in the gum/mint’s category as well as in consumer healthcare. He has experience working across geographies including Japan, Europe, and the U.S. Tony lives with his wife and two sons in Yarmouth, Maine

58 minFEB 29
Comments
Like a Boss: Tony Shurman - President and CEO of Jasper Wyman & Son

Gifford's Ice Cream CEO Lindsay Skilling

Lindsay Skilling is the CEO of Gifford’s Famous Ice Cream in Skowhegan, Maine. Gifford’s is a fifth-generation owned family business with roots back to the late 1800s. Today, Gifford’s sells almost 2 million gallons of ice cream, frozen yogurt, sherbet and sorbet each year and serves more than one million cones each summer from 5 family-owned and operated stands in Maine. You can find over 100 flavors in stores, restaurants and universities from Maine to Virginia to Nevada.

43 min2019 OCT 29
Comments
Gifford's Ice Cream CEO Lindsay Skilling

Like A Boss - Shawn Cunningham COO of Blue Tarp Financial

Press Herald CEO and publisher Lisa DeSisto sat down to interview BlueTarp Financial COO Shawn Cunningham Friday morning for our ‘Like a Boss’ series of interviews with local CEOs and business leaders. The series offers a behind-the-scenes look at their career paths, the ups and downs of running their businesses and the trends shaping them. BlueTarp Financial is a B2B credit management company in downtown Portland employing over 160 people. Founded in 1999, BlueTarp started with a credit program for building material suppliers, delivering cash flow up front so that they can invest in their business and grow sales while minimizing risk.

49 min2019 SEP 30
Comments
Like A Boss - Shawn Cunningham COO of Blue Tarp Financial

Like a Boss - Michelle Hood - Northern Light Health

Like A Boss is a live Q&A business event where you can hearinsightful, first-hand accounts of the realities of running a business. Our CEO and Publisher Lisa DeSisto interviews local CEOs and business leaders for a behind the scenes look at their career paths, the ups and downs of running their businesses and the trends shaping them. About Michelle Hood Michelle Hood is the president and CEO at Northern Light Health in Brewer, Maine. She came to Northern Light Health in 2006 after she served as president and CEO of the Sisters of Charity of Leavenworth Health System, Montana Region, as well as president and CEO of its flagship hospital, St. Vincent Healthcare. As president and CEO of Northern Light Health, she focuses on health care policy and design models at the state and national levels, positioning the system to be successful in a rapidly changing healthcare environment.

59 min2019 MAY 18
Comments
Like a Boss - Michelle Hood - Northern Light Health

Like A Boss: Deanna Sherman, president and CEO of Dead River Co

Portland Press Herald CEO and publisher Lisa DeSisto sat down with Deanna Sherman, president and CEO of Dead River Co., on Friday, Oct. 26, to chat about her work in the energy industry. Sherman oversees one of the largest energy companies in Northern New England. Founded in 1909, Dead River Co. is family-owned with over 1,000 employees serving customers in Maine, New Hampshire, Vermont and northern Massachusetts. Sherman joined the company in 1986 and has worked in leadership roles including district manager, regional manager and vice president of the Energy Division. She became Dead River’s president and CEO in 2016. Sherman is active in the community through her present and past board involvement with United Way of Greater Portland, Educate Maine, Junior Achievement of Maine, the Maine Energy Marketers Association and the University of Southern Maine Foundation. Like A Boss is a live Q&A business event where you can hear insightful, first-hand accounts of the realities of runnin...

60 min2018 OCT 31
Comments
Like A Boss: Deanna Sherman, president and CEO of Dead River Co

Like A Boss - USM President Glenn Cummings

On Friday, Sept. 7, 2018, publisher Lisa DeSisto sat down with Cummings, who began his academic career in Gorham as a high school history teacher and department head. He served as a faculty member at the Southern Maine Community College and was a long-serving member of the USM faculty. Prior to becoming president of USM, Cummings served as interim president of the University of Maine at Augusta. In 2010, he served former Pres. Barack Obama as deputy assistant secretary for the U.S. Department of Education and took over as president and executive director of the Good Will-Hinckley organization. Cummings is also a former Speaker of the Maine House of Representatives, Majority Leader, and chairman of the state’s Joint Committee of Education and Cultural Affairs.

57 min2018 SEP 10
Comments
Like A Boss - USM President Glenn Cummings

Like A Boss: Andrew E. Silsby, President and C.E.O. of Kennebec Savings Bank

Portland Press Herald Publisher Lisa DeSisto talks with Andrew Silsby about his career at Kennebec Savings Bank, which he joined in 1993. Silsby discusses why email isn't the best medium for solving problems, the bank's move into Freeport, and just how far ahead he likes to be with new technology. This interview was recorded July 27, 2017 in Augusta.

54 min2017 OCT 26
Comments
Like A Boss: Andrew E. Silsby, President and C.E.O. of Kennebec Savings Bank

Like A Boss: Chuck Hays - Maine General Medical Center

Portland Press Herald Publisher and CEO Lisa DeSisto chats with Chuck Hays, whose career took him from Massachusetts Maritime Academy, to marine nuclear engineering, to the helm of Maine General Medical Center. Hays talks about the role of MGMC in the community, and their objective, "... to be the leading community health care system in Maine, recognized for clinical excellence, customer satisfaction, financial stability and impact on community health."

41 min2017 AUG 4
Comments
Like A Boss: Chuck Hays - Maine General Medical Center

Laurie Lachance - President of Thomas College

Portland Press Herald President and C.E.O. Lisa Desisto talks with Laurie Lachance, the first female President of Thomas College, about how she came to that job and what Thomas College means to its students and the business community in Maine.

26 min2017 JUL 25
Comments
Laurie Lachance - President of Thomas College

Latest Episodes

Like a Boss Now - Kristen Miale, President of Good Shepherd Food Bank

Like A Boss Now is a series of live webinar interviews where you can hear insightful, first-hand accounts of the realities of running a business. Portland Press Herald CEO and Publisher Lisa DeSisto will interview Maine CEOs for insights on how they are managing, adapting, and problem solving in these ever-changing times. As a lifelong advocate for ending food insecurity, Kristen Miale, president of Good Shepherd Food Bank, has worked tirelessly to grow organizational partnerships throughout the state of Maine. She and her team of 80 work with a network of more than 400 nonprofit organizations to distribute 25 million meals a year, making Good Shepherd Food Bank Maine’s largest hunger relief organization.

38 minAPR 25
Comments
Like a Boss Now - Kristen Miale, President of Good Shepherd Food Bank

Like a Boss: Tony Shurman - President and CEO of Jasper Wyman & Son

Portland Press Herald Publisher and CEO Lisa DeSisto interviews Tony Shurman at the Portland House of Music in Portland Maine on February 28, 2020. Shurman is President and CEO of Jasper Wyman & Son (“Wyman’s”) the second largest brand in the retail frozen fruit category in the U.S. with its most notable product being wild blueberries. Founded in 1874, Wyman’s is a family-owned business headquartered in Down East Maine with an ongoing commitment to environmental stewardship, corporate social responsibility and product innovation. Prior to joining Wyman’s in 2017, Tony ran the Post Foods breakfast cereal business which includes brands such as Honey Bunches of Oats, Grape Nuts, Pebbles, and Post Shredded Wheat. Earlier in his career he worked in brand management roles in the gum/mint’s category as well as in consumer healthcare. He has experience working across geographies including Japan, Europe, and the U.S. Tony lives with his wife and two sons in Yarmouth, Maine

58 minFEB 29
Comments
Like a Boss: Tony Shurman - President and CEO of Jasper Wyman & Son

Gifford's Ice Cream CEO Lindsay Skilling

Lindsay Skilling is the CEO of Gifford’s Famous Ice Cream in Skowhegan, Maine. Gifford’s is a fifth-generation owned family business with roots back to the late 1800s. Today, Gifford’s sells almost 2 million gallons of ice cream, frozen yogurt, sherbet and sorbet each year and serves more than one million cones each summer from 5 family-owned and operated stands in Maine. You can find over 100 flavors in stores, restaurants and universities from Maine to Virginia to Nevada.

43 min2019 OCT 29
Comments
Gifford's Ice Cream CEO Lindsay Skilling

Like A Boss - Shawn Cunningham COO of Blue Tarp Financial

Press Herald CEO and publisher Lisa DeSisto sat down to interview BlueTarp Financial COO Shawn Cunningham Friday morning for our ‘Like a Boss’ series of interviews with local CEOs and business leaders. The series offers a behind-the-scenes look at their career paths, the ups and downs of running their businesses and the trends shaping them. BlueTarp Financial is a B2B credit management company in downtown Portland employing over 160 people. Founded in 1999, BlueTarp started with a credit program for building material suppliers, delivering cash flow up front so that they can invest in their business and grow sales while minimizing risk.

49 min2019 SEP 30
Comments
Like A Boss - Shawn Cunningham COO of Blue Tarp Financial

Like a Boss - Michelle Hood - Northern Light Health

Like A Boss is a live Q&A business event where you can hearinsightful, first-hand accounts of the realities of running a business. Our CEO and Publisher Lisa DeSisto interviews local CEOs and business leaders for a behind the scenes look at their career paths, the ups and downs of running their businesses and the trends shaping them. About Michelle Hood Michelle Hood is the president and CEO at Northern Light Health in Brewer, Maine. She came to Northern Light Health in 2006 after she served as president and CEO of the Sisters of Charity of Leavenworth Health System, Montana Region, as well as president and CEO of its flagship hospital, St. Vincent Healthcare. As president and CEO of Northern Light Health, she focuses on health care policy and design models at the state and national levels, positioning the system to be successful in a rapidly changing healthcare environment.

59 min2019 MAY 18
Comments
Like a Boss - Michelle Hood - Northern Light Health

Like A Boss: Deanna Sherman, president and CEO of Dead River Co

Portland Press Herald CEO and publisher Lisa DeSisto sat down with Deanna Sherman, president and CEO of Dead River Co., on Friday, Oct. 26, to chat about her work in the energy industry. Sherman oversees one of the largest energy companies in Northern New England. Founded in 1909, Dead River Co. is family-owned with over 1,000 employees serving customers in Maine, New Hampshire, Vermont and northern Massachusetts. Sherman joined the company in 1986 and has worked in leadership roles including district manager, regional manager and vice president of the Energy Division. She became Dead River’s president and CEO in 2016. Sherman is active in the community through her present and past board involvement with United Way of Greater Portland, Educate Maine, Junior Achievement of Maine, the Maine Energy Marketers Association and the University of Southern Maine Foundation. Like A Boss is a live Q&A business event where you can hear insightful, first-hand accounts of the realities of runnin...

60 min2018 OCT 31
Comments
Like A Boss: Deanna Sherman, president and CEO of Dead River Co

Like A Boss - USM President Glenn Cummings

On Friday, Sept. 7, 2018, publisher Lisa DeSisto sat down with Cummings, who began his academic career in Gorham as a high school history teacher and department head. He served as a faculty member at the Southern Maine Community College and was a long-serving member of the USM faculty. Prior to becoming president of USM, Cummings served as interim president of the University of Maine at Augusta. In 2010, he served former Pres. Barack Obama as deputy assistant secretary for the U.S. Department of Education and took over as president and executive director of the Good Will-Hinckley organization. Cummings is also a former Speaker of the Maine House of Representatives, Majority Leader, and chairman of the state’s Joint Committee of Education and Cultural Affairs.

57 min2018 SEP 10
Comments
Like A Boss - USM President Glenn Cummings

Like A Boss: Andrew E. Silsby, President and C.E.O. of Kennebec Savings Bank

Portland Press Herald Publisher Lisa DeSisto talks with Andrew Silsby about his career at Kennebec Savings Bank, which he joined in 1993. Silsby discusses why email isn't the best medium for solving problems, the bank's move into Freeport, and just how far ahead he likes to be with new technology. This interview was recorded July 27, 2017 in Augusta.

54 min2017 OCT 26
Comments
Like A Boss: Andrew E. Silsby, President and C.E.O. of Kennebec Savings Bank

Like A Boss: Chuck Hays - Maine General Medical Center

Portland Press Herald Publisher and CEO Lisa DeSisto chats with Chuck Hays, whose career took him from Massachusetts Maritime Academy, to marine nuclear engineering, to the helm of Maine General Medical Center. Hays talks about the role of MGMC in the community, and their objective, "... to be the leading community health care system in Maine, recognized for clinical excellence, customer satisfaction, financial stability and impact on community health."

41 min2017 AUG 4
Comments
Like A Boss: Chuck Hays - Maine General Medical Center

Laurie Lachance - President of Thomas College

Portland Press Herald President and C.E.O. Lisa Desisto talks with Laurie Lachance, the first female President of Thomas College, about how she came to that job and what Thomas College means to its students and the business community in Maine.

26 min2017 JUL 25
Comments
Laurie Lachance - President of Thomas College
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