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Podcast

Dear Anna: How Do I Sell to the Next Generation?

Combining sales and marketing with technology will give contractors a leg up against competitors

By Chris Gray, Jill Bloom, Group Publisher, Roofing Contractor, Anna Anderson
AnnaPodcast_sell_next_generation.jpg
March 17, 2025

In today’s digital world, Gen X and millennial customers are demanding a robust buying experience that includes facets like price transparency, image generation and education on what they’re purchasing. How, then, can contractors take advantage of this trend?

In this episode of “Dear Anna,” the question is posed to Anna Anderson, CEO of marketing company Art Unlimited, who explains how contractors should unify sales and marketing with technology to sell to the next generation of homeowners.

Roofing Contractor presents The Best of Success Podcast Show

Dear Anna: How Do I Sell to the Next Generation?

In this episode of “Dear Anna,” Anna Anderson, CEO of Art Unlimited, explains how contractors should unify sales and marketing with technology to sell to the next generation.

Your browser does not support the audio element.

It starts, she says, with contractors letting go of the idea that they have to disseminate information to customers through in-person consultations or in-house demos. These old-school methods may be tried and true but when it comes to selling to younger generations, Anderson says it’s about a more user-friendly and hands-off experience.

Through technology powered by artificial intelligence, contractors can create marketing and sales experiences that include everything from intractable presentations to price transparency.

“What we also see is the consumer is able to experience what I would call a ‘frictionless experience’ with your brand,” she said. “And that frictionless experience is something that we're seeing this newfound younger millennial and Gen Xer begin to say, ‘Hey, I have the purchasing power that I want to have this different experience than my parents had, than my grandparents had.’”

Whether it’s building an “autonomous agent” that can sell on your company’s behalf or what technology is available to optimize marketing, Anderson is here to answer your questions. For more details about merging technology with sales and marketing, listen to the full podcast here.

KEYWORDS: AI (artificial intelligence) Art Unlimited Dear Anna marketing millennials podcast sales

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Chrisgray

Chris Gray is the former editor of Roofing Contractor and Roofing Supply Pro. He has worked in the fields of journalism and copywriting for nearly 20 years, ranging from local print newspapers to the multi-media promotion of international artists.

Reach him at 248-244-6498 or grayc@bnpmedia.com.

Jill bloom

Jill Bloom is the innovative Group Publisher of Roofing Contractor, Walls & Ceilings, Building Enclosure, Roofing Supply Pro, and the highly regarded Best of Success event. With a deep commitment to advancing the roofing, construction, and building enclosure industries, Jill oversees a robust portfolio of publications, podcasts, and events that empower professionals with knowledge, inspiration, and connections.

Her brands deliver exceptional value across multiple platforms, including:

  • Techos y Más, the Spanish-language newsletter of Roofing Contractor.
  • Safety Advisor, a newsletter focused on critical resources for jobsite safety.
  • Thermal Talk, a newsletter focused on insights and news for the insulation contractor.
  • eRock, a leading newsletter for drywall contractors.
  • The Enclosure Experts podcast, offering architects deep insights into building enclosure technologies.
  • If Walls Could Talk, a podcast dedicated to exploring trends and innovations for the wall and ceiling contractor.
  • The Best of Success Podcast, providing thought leadership and practical advice for roofing professionals.

Jill’s passion for professional development and fostering industry connections is exemplified by the Best of Success event, a premier gathering of contractors, suppliers, and thought leaders for unmatched education and networking.

Anna anderson art unlimited

Anna Chapman Anderson, CEO of Art Unlimited, has grown up working in the marketing industry. As a second generation owner, Anna is leading Art Unlimited within multiple industries and specialties. She speaks on national stages across the United States and works alongside business owners helping them obtain success. She is a recipient of the Joel Labovitz Entrepreneurial Success Award. Anna is an active member in Roofing Technology Think Tank (RT3), National Women in Roofing (NWiR), and Business Network International (BNI).

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