In this episode, we had the pleasure of speaking to Bobby Cooper, who specializes in building high-growth tech startups. With nearly 15 years of experience in customer-facing roles, Booby has held leadership positions at Tapcart, Weave, and InsideSales.com - consistently driving success and growth through innovative customer success strategies.
Bobby has redesigned the delivery of the customer success experience, focusing on a more results-driven onboarding process and a data-driven customer success approach.
Bobby shares his unique take on a common CS belief, learnings and observations from his CS journey, advice for aspiring CS leaders, and perspectives for the future.
That relationships matter the most in Customer Success.
Of course, relationships are important – but too many companies place too much emphasis on the relationship between the CSM and the customer. The focus should be on the relationship between the customer and the company (product), not just the CSM.
When a customer buys a product, they are signing up for the product and the results it promises to deliver, not necessarily to build a relationship.
Plus, CSMs have different personalities, skills, and lengths of tenure at the company. This can result in favoritism, leading to some customers being left behind while only the noisy ones get attention. It also means too much emotion in our calculations of what it takes to save a customer, leading to inconsistent customer experiences.
The key is to control the relationship through data and standardized processes. The CSM's role remains the same—they provide the human element to drive that experience. However, the data and AI layer help them know who to talk to, and what they need to do – at the right time.
I have a background in sales and entrepreneurship, having started several small businesses and having worked as a sales leader for many years.
I met the CFO of InsideSales.com, and he mentioned they were looking for sales leaders to help guide customers through the adoption process of their software and to maximize customer results. This role eventually turned into the customer success team.
I used my sales skills to teach customers how to sell better using our product. I realized that sales wasn't just about the initial transaction any more but about building long-term relationships through successful outcomes. I fell in love with the retention and renewal model in SaaS, understanding that this revenue was more important than net new bookings.
Obsess about the customer's results.
I retained many customers through personal relationships, but I also had customers churn despite a great relationship. Results matter.
If you don't know what your customer's results are, figure out how they measure the ROI of your product. Ask them, "What makes this product valuable to you? How do you measure the ROI on it?" Then, obsess about that.
Key metric is Net Revenue Retention.
But there’s another less-discussed reason.
In an ideal world, companies wouldn’t need to invest in customer success. You’d have a perfect product that’s easy to use and manage, with clear, impactful results. Sales and marketing teams would pitch the value proposition perfectly, so only the right customers buy your products. And you’d have perfect customers who prioritize using your product to solve their problems. But in the VC-backed SaaS world, that’s not the reality.
Companies release minimally viable products to prove market fit before heavily investing in development. This means customers often buy products that aren’t fully ready to do the job.
CS teams fill the gaps in this model. They ensure the product is used correctly and is a priority for the customer.
For example, one of my favorite customers had a mobile app for sales. We knew that sending one push notification a month could generate about $500,000 in sales, but sending one a week could generate $1.2 to $1.5 million. When I asked why they didn’t send weekly notifications, their response was genuine: they were managing multiple responsibilities, and push notifications weren’t a top priority.
This shows that customers can forget to use your product or prioritize it. The CSM's job is to remind customers of the product and the problems it solves. At our company, we use customer health scores and monitor usage to reach out to customers when their engagement drops, reminding them of the optimal usage strategies.
AI is reshaping every aspect of SaaS companies, from internal operations to customer experience and overall scalability. Everyone is trying to discover how to use it effectively, and while there's no definitive handbook on scaling with AI yet, it should be a top priority for CS leaders.
Dozens of companies are creating AI-driven solutions to address micro problems and use cases. I recently saw a demo of AI agents acting as CSMs. They looked, talked, and had personalities like humans, telling jokes and interacting well.
I don't think that's the immediate problem we need to solve. Customers aren't ready for it yet, and there's a lot of skepticism.
I believe AI should be leveraged first for business operations and not for critical customer interactions. We should prove AI's value by improving operational efficiencies and empowering CSMs to have more meaningful human interactions. AI can help solve the inconsistency in customer experiences by summarizing context, providing data to CSMs, etc. – ensuring a more consistent experience regardless of who the customer interacts with.
I recall a quote I saw on LinkedIn: "I don't want AI to do my artwork and write my poetry so I have more time to do my dishes and fold my laundry. I want AI to do my dishes and fold my laundry so I have more time to do my artwork and write my poetry." This sums up how I view AI.
Definitely. AI’s role is to give more information, context, and power to humans so they can have more impactful interactions with customers.
I recently talked to a company using AI to cut down on note-taking during customer journey handoffs. This means sales reps don't have to spend as much time documenting every detail, and on-boarders don't start their day sorting through potentially flawed notes.
AI can help teams seamlessly share knowledge, reduce frustration, and make everyone look smarter by ensuring they understand the customer journey context, even if they weren't part of every step.
