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Embark on a journey through customer success with Dana Booker, Senior Strategic Customer Success Manager at LearnUpon. Dana shares valuable insights on mastering customer churn, employing curiosity and empathy in CSM, and building cross-functional success. Learn innovative strategies for managing churned accounts with palliative care, ensuring positive experiences and potential return opportunities. Explore the pivotal role of curiosity and empathy in fostering stronger customer relationships, and understand how cross-functional collaborations elevate customer success at LearnUpon.

  • If a customer is churning, they should still receive your highest level of service. Palliative care for accounts that will move along should include opportunities to share feedback and to take advantage of new features, just as for your incumbents. There is always a possibility the customer will be back one day, and even if they do not return, your excellent service through their migration off your platform will help to ensure that when your company’s name is mentioned, they will only have positive things to say. Additionally, if your stakeholders from the churned account move to a new organization down the line, they are more likely to refer their new organization to your company.
  • The best CSMs are those who are able to be curious and empathetic when handling customer accounts. Curiosity will enable you to become closer to your customers, to understand their objectives and desired results, and to proactively and prescriptively offer solutions before they are even needed. Empathy takes this a step further, where you can see things from the customer’s perspective and truly understand the challenges they face and what success looks like to their organization. Being empathetic and curious will lead to stronger, more successful engagements with customers.
  • The best CSMs build robust and trusting cross-functional relationships with the internal teams they work with. By understanding the goals and challenges for other organizations such as Sales, Product, Legal, Support and Marketing, a CSM can help bring the best of their company to their customers. Taking this a step further, the best CSMs invest in learning how to speak the language of other departments to facilitate easier communication and to achieve faster results. The closer you are to the other internal teams at your organization, the easier it will be to bring value to those organizations and to your external customers.

About Dana Booker

As a Strategic Customer Success Leader at LearnUpon, I leverage my JD degree, my affective empathy, and my passion for diversity, equity, inclusion, and belonging (DEIB) to help our largest clients and partners achieve their learning and business goals. I have over two years of experience in customer success, operations, and social networking, and I am a certified Freshbooks consultant and a proficient speaker of English and Spanish.


I love my job because I get to work with a talented and supportive team that trusts me to lead and innovate. I also enjoy learning and growing every day, and applying my creativity and curiosity to solve problems and create value for our customers. One of my proudest achievements at LearnUpon was creating our first-ever DEIB OKRs in 2022, and hosting quarterly internal diversity info-shares. I am also an AI artist, and I use artificial intelligence to increase representation by creating unique and expressive artworks that reflect my vision and personality.

About Company


LearnUpon was founded on a belief: learning should be simple, and its impact should be big. And today, we’re helping 1,300+ businesses around the world do just that. By championing simple, learner-centric experiences and results-focused support, LearnUpon gives your teams the tools to deliver learning that impacts what matters – performance, retention, and growth.


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