I was wrapping up a phone call with an insurance company customer. We were discussing an expansion deal being worked on by his procurement department for my company’s employee performance management platform. As I started to say my goodbyes, he interrupted me to say, “Your vision. Your solution and team. Everything’s great. I can’t praise you enough. But you need to know, we are a difficult customer.”
I was wrapping up a phone call with an insurance company customer. We were discussing an expansion deal being worked on by his procurement department for my company’s employee performance management platform. As I started to say my goodbyes, he interrupted me to say, “Your vision. Your solution and team. Everything’s great. I can’t praise you enough. But you need to know, we are a difficult customer.”
That was an amazing way to end a positive, productive conversation. But it got me thinking about Coach Sterimbaum. He was my volleyball coach. Gave the toughest challenges. The hardest practices. Really pushed me and my teammates. He was…difficult. But I made it to the youth national team. And, to this day, I draw on the tough love he gave me.
I also realized each one of the half dozen or so customers I had just offered as references to an investor could be described as difficult. In slightly different ways. Customers at a big brand mobile phone sales company, a large BPO, a global telco, another insurance group, and a couple of others are each like Coach Sterimbaum.
I want difficult customers. And you should too. Let me explain.
They know success
Difficult customers aren’t mean. They’re don’t enjoy harassing your customer success team. Quite the opposite. They have a clear vision with an even clearer view of what success looks like. And, they’ll be demanding to achieve it…without compromise. On your or their part.
I’m sure you’ve been in situations where success hasn’t been defined and, yet, work is underway. But since difficult customers know what success is, or needs to be, it’s totally understood by everyone involved. You’ll know what you’re driving toward and why.
They’re difficult with everyone
Difficult customers are difficult with everyone. Especially within their own organizations. And you’ll want that. Because their difficult-ness will unclog bottlenecks and ensure things move forward. They won’t hesitate to enlist leadership. Gain IT’s support. Really do whatever’s needed, with whomever, to get the needed focus for a successful deployment.
They’ll make you ready for the next challenge
And like Coach Sterimbaum, difficult customers will push you past what you think you’re capable of doing. They’ll push you beyond your current level of service. Force more from your processes. Insist on greater product functionality. They’ll push. And push some more. Ultimately, it’ll be for your own good.
Another common characteristic of difficult customers is they’re early adopters. The value of their help in creating a better product that really fits with the wants and needs of the market can’t be calculated. Along with that, the rigors they put you through means you and your team will be able to serve every other customer better. For example, the normal repetition of process management when done for a difficult customer will make your organization the business equivalent of a super-sharp drill team.
Let me add, a difficult customer doesn’t want you or your team to simply accommodate them. They’re about reaching a goal. And are often driven to do so. If you believe success can be met taking a different path – one that keeps your product core unchanged – tell them. Then get there.
Madeleine Freind is a senior Customer Success leader with deep experience building and scaling SaaS and managed services businesses. At Centrical, she leads the Customer Success teams across North and South America, partnering with clients to drive measurable business impact through the platform.
Before joining Centrical, Madeleine was Head of Customer Success at Quantifind, an AI-powered analytics company, where she led strategic relationships with brands like Hershey’s, KFC, J.P. Morgan Chase, and Dunkin’ Brands. Her ability to translate complex data into clear, actionable solutions consistently helped customers achieve their goals.
Earlier in her career, Madeleine spent over a decade on the agency side, managing CRM and digital marketing programs for Fortune 500 companies through smart, data-driven strategies.
Michael Ciancio serves as the Chief Marketing Officer (CMO) at Centrical, bringing decades of experience in marketing and go-to-market strategy. In this role, he leads the company’s global marketing efforts to drive brand growth and market expansion.
Prior to joining Centrical, Michael held marketing leadership positions at notable technology companies, including IntelePeer, Infor, and Vonage. Throughout his career, he has successfully guided teams in scaling products, strengthening brands, and significantly expanding market presence.
Michael’s expertise lies in scaling high-growth software companies, particularly in AI, performance management, and employee engagement solutions for customer experience teams. His strategic vision and leadership continue to be instrumental in advancing Centrical’s mission to transform how organizations engage and motivate their frontline teams.
Michael holds a Bachelor’s Degree in Economics from Gettysburg College and a Master of Business Administration (MBA) in Marketing from Montclair State University.
Natalie Roth brings over 15 years of experience in brand and product marketing for SaaS solutions. Before joining Centrical, she was Senior Product Marketing Manager at Frontline Education, where she led go-to-market strategies for enterprise K-12 solutions and played a key role in integrating and positioning products following multiple acquisitions.
Previously, Natalie served as Director of Marketing at Accelify Solutions, where she drove marketing strategy, new product launches, and customer communications. She played a pivotal role in business growth, expanding market presence, and deepening client engagement, contributing to the company’s success and eventual acquisition by Frontline Education.
Natalie holds a BA in Creative Writing and Digital Media from New York University, graduating magna cum laude.
Linat Polak Mart has more than 15 years of expertise in managing product strategy and operations in high-volume organizations.Previously, she held the role of Head of Product Experience and Communications for LivePerson, a leading Conversational AI platform, where she played crucial part in delivering significant product innovation and customer growth. Prior to her time at LivePerson, she held multiple senior product roles at NICE, a leading enterprise customer experience (CX) software provider, including Director of Product Portfolio and Director of Product Management.
Linat holds an MBA from Tel Aviv University and a BA in Computer Science from Reichman University (IDC Herzliya). She graduated magna cum laude from both institutions.
“CX leaders should stop isolating contact centers from other departments. Customer experience is increasingly cross-functional. In 2025, integrating CX insights across the organization will be critical to delivering seamless and cohesive experiences.”
Tompkins comes to Centrical with more than 25 years of experience in software and hardware sales. Prior to joining his role as Chief Revenue Officer at Centrical, he was CEO at Workspot. He held the position of Chief Revenue Officer at IGEL as well as senior sales leadership positions with Red Hat, Hewlett Packard (now Hewlett Packard Enterprise), and Citrix.
Tompkins holds an MBA in Business Administration and Management from the University of Virginia, Darden Graduate School of Business Administration and served in the US Navy as a Nuclear Propulsion Technician.
“Knowledge Management: It is not exactly underrated but it will be bigger than what it is in 2025. Vendors are likely to boost R&D investment in knowledge management for contact centers in 2025.”
“Human-centered AI, where AI is used not just to automate and drop money to the bottom line, but used to service up insights to support team members and delight customers. I see generative AI with conversational context and tonal analysis as pretty critical here.”
“The future? Goodness, there’s so much, but I really believe 2025 is the year of community. We’re not just taking tickets anymore—folks we’re drawing people in, getting proactive, and co-creating with customers. Community will become a normal service channel, with customer service workers facilitating and adding value.”
“The myth that technology/AI is a quickly implemented CX superpower. Companies will realize that we can’t harness a lot of these gains without quality data that is clean and well-organized.”
“By 2025 the buzzword omnichannel may be on its’ last leg. Customers want their issues resolved quickly and accurately and they would prefer not to need to contact us in multiple channels that we can see at one time.”
“For 2025, the main trend I’m watching is ‘AI agents’—bots powered by AI that are becoming more autonomous. Unlike basic responses, these AI agents can handle end-to-end customer interactions, reducing the need for human intervention. Expect significant developments from vendors.”
“Stop talking about AI. It’s like talking about the internet being a thing. It’s here. The better focus is start thinking about how AI enhances the lives of your team. So stop talking about AI and start doing something about it.”
“AI and CX will drive hyper-personalization, using consumer data to segment customers, deliver key messages, and provide fast, accurate responses. Technologies like chatbots and predictive analytics will close the gap between brands and consumers.”
“The blending of CX and EX will accelerate. The days of reducing friction for customers at the expense of employees are over. Indeed, because AI-enabled customer experiences often require AI usage by customer-facing employees, leaders will have to ensure a frictionless work experience to drive AI adoption and deliver value.”
Read Stephanie’s full interview
One myth that will be debunked in 2025?: “Customers are on the edge of their seat waiting to hear what you have to say. We need to learn about what’s important to customers by asking more questions.”
Gal founded Centrical (previously GamEffective) in 2013, with the vision of helping companies empower their employees’ performance, making them the center of business success.Prior to that he was CEO of Gilon-Synergy Business Insight, a national leader in Business Intelligence. In 2010, Gilon-Synergy was acquired by Ness Technologies (NASDAQ:NSTC) and Gal went on to serve as Senior VP at Ness, and was member of its executive management.
Prior to that he was VP customer relations and operations at Deloitte Consulting. He also worked at EDS and Bashan. He holds a MBA degree in Marketing and Information Technologies from the Tel Aviv University.
Daphne has over 15 years of experience in Customer Relations and Retention in both B2B and B2C environments. Her area of expertise is leading customer success, consulting and global professional services teams within public and private sector companies. She is focused on leading teams to grow the partnership with our clients.
Prior to Centrical, Daphne worked software and service companies in the online marketing and gaming industry.
Daphne holds MA in Statistics – Specialization in Operations Research and a MBA degree, both from the Hebrew University of Jerusalem.
Ella Davidson is responsible for managing Centrical’s employee relations worldwide, including organizational development, talent management, benefits and recruitment. Ella has more than 18 years of human resources management experience. Prior to joining Centrical she was vice president of human resources at myThings and OpTier – leading SW companies, and consulted numerous entrepreneurs and startups in the Israeli hi-tech industry and Israel and in the US.Ella holds a B.A in Psychology from the Hebrew University and MSc in Organizational Behavior from Recanati Business School at Tel Aviv University.
Ariel has over 16 years’ experience in a wide variety of R&D leadership roles. He is highly experienced at building R&D teams from the ground up, driving high levels of accountability and ownership and setting up automation infrastructures. For the past 10 years Ariel has managed both in-house and offshore development teams at companies ranging from startups to enterprise organizations.
Prior to joining Centrical, Ariel served as VP of R&D at Worthy.com where his team dramatically improved product stability, quality and execution. Before that, he was VP R&D at Applicaster where he led infrastructure changes from project to product. Ariel has also held various R&D positions at Retalix (later acquired by NCR).
Ariel holds B.sc in Computer science & Math, and MBA degree in Information Technologies, both from Bar Ilan University
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