Windward Group
strategic consulting to multi-channel brands
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Rebecca L. Jewett, Managing Partner

Rebecca Jewett
Becky is a founding principal of Windward Group, a national consulting partnership specializing in strategic issues for multi-channel organizations.

As President of Norm Thompson Outfitters, Inc., a $200 million company, comprised of three brands: Norm Thompson, Solutions and Sahalie (Early Winters), she doubled the size of the business, with Solutions growing more than four-fold. During her tenure the company built a sophisticated customer database & a robust Internet business, developed critical marketing competencies and became a thought leader in corporate sustainability.

She served as President of Chadwick’s of Boston, the original off-price fashion catalog. She repositioned the company and grew its net sales from $78 million to $450 million in five years. She has also held positions of Senior Vice President-Marketing for The Talbots, Inc. and Vice President-Marketing for The Swiss Colony, Inc. 

She was the 2004 Chairman of the Board of Directors of the Direct Marketing Association and a current member of the Board. As Chair, she catalyzed change, revitalizing the Board. She initiated the development of a strategic

plan, organized the review of the major revenue stream (Annual Conference) and transitioned new leadership, commissioning the Search Committee of which she was member and which hired the current CEO.

She is past Chairman of the Board of Directors of the United Way of Columbia Willamette and is former President of the Board of Trustees of Oregon Ballet Theatre.

She holds an MBA from Harvard University Graduate School of Business Administration, a M.Ed. from Lesley College and is an alumna of Wellesley College, where she was a Wellesley Scholar.

With Bobby Orr and Herbert Douglas, she raised over a million dollars for the Cardinal Cushing School and Training Center, a residential school helping severely disabled children prepare for a functional adult life. The School honored her as 1994 Springtime Humanitarian. Catalog Success Magazine named her Cataloger of the Year in 2002.

She is a member of the Board of Directors of the Vermont Country Store.

John S. Craig, Partner

John Craig
A founding partner of Windward Group, John has 25 years of experience in Direct Marketing. He began his career at Sara Lee Direct, a division of Sara Lee Corporation, where he oversaw the launch of two women’s apparel catalogs: One Hanes Place and Just my Size. Under John’s leadership the business grew to over $200 million and the Customer database to over 7 million names.

He pioneered E-Commerce at Sara Lee, building an E-Mail database of over 1 million names and driving a third of the sales to the web. While at Sara Lee John assisted in direct marketing for other premiere Sara Lee brands: Coach Leatherwear, Fuller Brush and Wolfermans.

Most recently John was Vice President of Marketing for Kaplan Early Learning Company, a retailer of educational materials to the Early Childhood Education Market. At Kaplan, John led business innovation, building a Marketing Database, launching a new website that increased revenues 300% and implementing innovative sales and marketing collaborations.

Having overseen strategy development and implementation of marketing databases at both Sara Lee and Kaplan, John has specific expertise in customer acquisition, database management, calculation and application of lifetime value and maximizing house file yield through intelligent statistical modeling.

He has served as Board Chair for Samaritan Ministries, a soup kitchen and homeless shelter, Hosanna House, a substance abuse recovery program, and as a board member for Industries for the Blind. He has led numerous relief teams to Haiti to provide medical care, dental care and construction workers in the poorest country in the Western Hemisphere.

He holds an MBA from the Kenan Flagler School of Business Administration at the University of North Carolina at Chapel Hill, an MS in Education from Indiana University and a BA in Journalism from the University of North Carolina at Chapel Hill.

John also serves as an adjunct marketing professor at Wake Forest University.

Steven J. Montaperto, Partner

Steven J. Montaperto

Steve is a partner at the Windward Group, a national consulting organization specializing in multi-channel retail companies.  He has held executive and general management positions in early stage growth companies as well as in mature businesses during his career in the direct marketing industry.

At J. Crew, he was responsible for developing the systems and processes that guided the business from early stage testing through $100 million in revenue.  At Tweeds, the first venture capital financed catalog company, he led the strategic planning process and built the infrastructure that resulted in a startup business growing to $70 million in sales over four years.

More recently Steve served as General Manager of Fingerhut’s Woman’s Apparel Group, where he repositioned three businesses, Bedford Fair, Lew Magram and Brownstone Studios, which were acquired in bankruptcy.  Under his leadership, the group grew to $150 million in sales and generated record profits.

Steve has been active in the Direct Marketing Association and is a former Chairman of the Catalog Council.  He holds an MBA from the University of Connecticut and a BA from Manhattanville College.