At Insightful, the collaboration between Sales and Customer Success goes beyond day-to-day operations - it is a strategic partnership built on continuous learning, mutual understanding, and aligned business goals.
Regular cross-functional workshops are designed to empower teams with the tools and skills needed to drive customer satisfaction, meet key business goals, and support ongoing professional development. These sessions also strengthen collaboration between Sales and Customer Success by deepening mutual understanding and refining processes - like adopting the MEDDICC framework - to better identify opportunities and close deals with confidence.
Through these workshops and a shared commitment to professional development, both teams are not only improving internal processes but also elevating the overall customer experience.
To dive deeper into the impact of these workshops and collaborative efforts, we spoke with our Customer Success and Sales leadership team - Jack, Jana, Leo, and Marko. Here are their crucial takeaways.
Jack (Head of Customer Success): We put on workshops with three goals in mind: give our team the necessary tools to ensure our customers are getting the best service possible, ensure we are better prepared to meet our KPIs around retention, growth, and customer satisfaction, and offer opportunities for professional development that will help our team be their best in the roles they are in today, and prepare them for opportunities that will arise for them professionally in the future.
Leo (VP of Sales): These workshops not only nurture critical skills in both Account Executives and Customer Success Managers, but also deepen our collaboration, and understanding of each other’s roles, perspectives and nuances. And for sales it is also about refining discovery practices and embracing MEDDICC as a methodology which we are implementing.
Sometimes, we might not fully grasp the business case or the critical metrics that drive a customer's success, and that is where MEDDICC comes in. It reminds us of the key areas to focus on and the impact-based questions we need to ask. It helps us identify risk early, guide deals further down the funnel, and ultimately, close with confidence.
We then looked further and asked: How would you describe the current state of collaboration between Sales and Customer Success? What is working well and where do you see room for improvement?
Jack: Collaboration between our two teams has always been relatively solid, simply due to the nature of our respective roles. I see Sales and Customer Success essentially being two sides of the same coin. With Leo stepping in as our VP of Sales, we have seen a big uplift in that collaboration - he has been leading cross-functional trainings, and we have worked closely together on aligning our processes so that our teams are speaking the same language.
The immediate opportunity here is deepening our partnership when Sales identifies new opportunities within our existing customer base. That way, we ensure our customers always have access to the best resources for the particular phase of the customer journey they are on at any given time.
Marko (Sales Manager): Collaboration between the two teams is already at a high level, but we are always looking to refine it. One area I see we could improve is the transitioning phase for a client - from Sales to Customer Success. Clearer ownership of responsibilities in those early steps would make the hand-off smoother and ensure both teams stay aligned.
Why do you believe effective collaboration between Sales and Customer Success is crucial for the overall success? How do you see these workshops contributing to improved alignment and performance between the two teams?
Leo: I appreciated getting a unique perspective from our CSMs during these workshops. Seeing how they research for calls, approach personas, and think through the customer lens gave us new insights. It is not just about how Account Executives think - it is about understanding each other’s methods so we can build a more cohesive customer experience.
Jana (Customer Success Team Lead): Both teams are among the first point of contact to the customer and therefore, a seamless handoff between Sales and Customer Success is crucial. That is why sharing enough information between the two teams is important.
Beyond workshops, what other initiatives are in place or planned to further strengthen collaboration between Sales and Customer Success? How are you helping team members continue developing new skills and mutual understanding?
Jack: One area I would like to focus on this year for my team is strengthening their data analysis and KPI tracking skills. While the data we consider, and KPIs we work towards in Customer Success differ from those in Sales, this skillset is absolutely transferable and worthwhile for both of our teams to develop.
Leo: As we identify areas of opportunity, we are committed to creating additional workshops or sessions tailored to those needs. Jack and I have been discussing how we can focus more on account planning, account mapping, and building strong relationships from the start.
The workshops are more than just training - they are a space to connect, align, and refine the way we work together. Through them, stronger communication, shared processes, and a culture of curiosity, both teams are focused on building the skills and alignment needed to create a seamless, impactful customer journey.
This partnership isn’t a one-time initiative but a long-term investment in our customers’ success.
