Richard Convery: From Executive Assistant to Customer Success Leader A Journey of Success

As a Customer Success Manager, Customer Success Leader, and now the founder of the onboarding platform Ascendr, my career journey has been filled with exciting experiences and opportunities. In this article, I will share how I stumbled upon the world of Customer Success, rose to leadership positions, and eventually found my calling in creating my own platform.

Falling into Software

Fifteen years ago, I had the chance to work with Rachel Elnaugh, one of the entrepreneurs from the popular TV show Dragons Den who used to own Red Letter Days. I had always aspired to be an entrepreneur myself, so I sent out my CV to various celebrity entrepreneurs. Surprisingly, Rachel offered me a position as her Executive Assistant, and I eagerly accepted the opportunity.

During my time with Rachel, I discovered that she was using an ERP (Enterprise Resource Planning) platform. This sparked my interest, and I began building a relationship with the software team. This is how I unintentionally stumbled into the world of software and technology.

Exploring Various Roles

Since entering the software industry, I have had the privilege of working in diverse roles, gaining valuable experience along the way. I have dabbled in Support, Business Analysis, Systems Analysis, Implementations, and Onboarding. As time passed, I progressively moved into more challenging positions, such as team lead and manager.

To enhance my technical skills and understanding, I spent a couple of years on Codecademy, where I taught myself various programming languages. This not only piqued my interest but also enabled me to engage in more meaningful conversations with customers, especially those from technical backgrounds. Having a grasp of the technical aspects of a product is crucial when dealing with customers who possess a certain level of technical expertise.

The Emergence of Customer Success

Customer Success as a concept is relatively new, having gained prominence only in recent years. I vividly recall going for a job interview when the interviewer mentioned the term “Customer Success” as a potential job title for me. This was about seven or eight years ago, and I had never heard of it before. It sounded strange at first, but I soon realised it was a legitimate role in the business world.

What intrigued me most about Customer Success was its multidimensional nature. It serves as the central point for various aspects of business operations. A successful Customer Success Manager requires excellent project management skills, sales acumen, and the ability to effectively communicate with development teams. It is a role that allows for versatility, encompassing a diverse range of responsibilities and opportunities.

The Joys of Customer Success

One of the most fulfilling aspects of being in Customer Success is the variety that comes with the job. You can engage in a wide array of tasks, all while maintaining a focus on customer satisfaction. Additionally, being customer-facing opens the door to numerous exciting opportunities, such as visiting customer sites around the world. Personally, I have been fortunate enough to travel extensively for work, and it has added a unique dimension to my career.

Another highlight of Customer Success is the opportunity to build meaningful relationships with customers. By understanding their needs and goals, I can provide them with the necessary support and guidance to achieve success with our product. Building these relationships allows for a deeper connection with customers and fosters loyalty and long-term partnerships.

The Birth of Ascendr

Throughout my journey in Customer Success, I realised that the onboarding process is often overlooked, despite its critical role in customer satisfaction and retention. This realisation led me to create Ascendr, an onboarding platform that streamlines and enhances the onboarding experience for customers. With Ascendr, companies can ensure that customers have a smooth and successful onboarding journey, setting the stage for long-term success.

The platform offers a range of features and functionalities designed to optimise the onboarding process. It provides step-by-step guidance, interactive tutorials, and personalised support to help customers navigate their initial interactions with a product or service. By investing in a robust onboarding experience, companies can significantly improve customer satisfaction, reduce churn rates, and drive revenue growth.


My career in Customer Success has been a journey of discovery, growth, and innovation. From falling into software through a chance encounter to founding my own onboarding platform, I have experienced firsthand the evolving landscape of Customer Success. I have embraced the challenges and joys of the role, building strong relationships with customers and witnessing their success.

As the founder of Ascendr, I am committed to revolutionising the onboarding experience and helping companies unlock the true potential of their customers. By prioritising stellar onboarding, businesses can foster customer loyalty, drive positive word-of-mouth, and ultimately achieve long-term growth and success. Together, let’s embark on a journey of customer success and build thriving partnerships.

Ready to take the next step? Sign up with Ascendr today and let us help you create an exceptional onboarding experience for your customers.

Richard is a visionary leader with a proven track record of driving customer success and driving organisational growth. With over 15 years of experience in the industry, he has developed a unique skill set in strategy development, cross-functional team management, and business transformation. His ability to develop and implement innovative solutions while fostering a positive team culture has earned him a reputation as a thought leader in the field.

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