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Podcast

Dear Anna: How Do I Never Lose a Customer Again?

Learn tips and strategies on winning over customers and making them lifelong clients

By Chris Gray, Jill Bloom, Group Publisher, Roofing Contractor, Anna Anderson
Anna-Anderson-headshot-podcast-title-slide
Image by Roofing Contractor
October 29, 2025

In the hustle to secure the next project or a new customer, roofing contractors may lose sight of the gold mine they’re sitting on to gain more jobs.

It’s a point Art Unlimited CEO and marketing expert Anna Anderson has shared before, but it’s perhaps even more relevant today as businesses struggle against rising costs and economic uncertainty. That’s when they should turn to their existing customer database.

Roofing Contractor presents The Best of Success Podcast Show

Dear Anna: How Do I Never Lose a Customer Again?

With the price of everything rising, it’s more important than ever for roofing contractors to gain new customers. But winning them over should be more than simply locking in a new project. Art Unlimited CEO Anna Anderson explains how roofing contractors can convert customers into lifelong clients with tips from the book "Never Lose a Customer Again."

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“How are we reconnecting? How are we ensuring that there's delight not only in the first project that you're able to accomplish for them? And yet, what is that next project? And how can you make sure that relationship continues to grow and thrive?” Anderson said.

Not only are existing customers a key source of revenue, but cultivating new customers into lifelong clients instead of constantly chasing new ones is a surefire way to guarantee business.

With that in mind, Anderson chats with RC Publisher Jill Bloom about “Never Lose a Customer Again” by award-winning speaker and business consultant Joey Coleman. The book’s subtitle says it all: “Turn Any Sale Into Lifelong Loyalty in 100 Days.” It goes into what the process looks like of winning over customers in that short period of time, broken down into eight different phases, like “Assess,” “Affirm,” and “Acclimate.”

“What we see is, if you do not create a great customer experience in that first 100 days, statistically, 60 to 70% of customers will defect,” Anderson said. “So you need to make sure you’re on top of that customer experience and communication in that 100-day mark.”

Listen to the full podcast for more details about the eight phases of winning over a customer and Anderson’s insights into how to apply this as a roofing contractor. For more podcasts like this, check out our “Dear Anna” series.

KEYWORDS: Art Unlimited CRM software customer service Dear Anna lead generation marketing podcast strategy

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Chrisgray

Chris Gray is the 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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