Challenge
Sendlane is a design-forward marketing automation platform for eCommerce businesses. They provide email and SMS messaging with sophisticated real-time analytics, deep data integrations, and A/B testing optimization tools. Sendlane was founded by three successful digital marketers, agency owners, and eCommerce entrepreneurs who wanted to build a better email marketing platform, as nothing available met their needs. They foresaw a shift in eCommerce from larger, more established brands, to individuals starting their own small business. They needed easy-to-use tools to help them maximize revenue without needing an experienced designer or marketer. Their strategy focused on sophisticated automations, "done for you" templates, and AI-driven segmentation and scheduling to ease the burden for entrepreneurs who wanted to focus on their core competency instead of marketing. Challenges Product-Market Fit After some strong initial traction, Sendlane found itself in a common failure pattern. They were struggling with retention and adoption of their new advanced features. Their growth was anemic, LTV was low, and support cost was high. They had reached the chasm of Product-Market Fit. At this point, the co-founder and Chief Product Officer hired me to be his executive coach and product strategy consultant. My first order of business was to understand their customers and why they were churning. It turned out, Sendlane’s customers were not experienced digital marketers. They were entrepreneurs trying to build an eCommerce business. They weren’t savvy enough to build a successful email marketing campaign, so the advanced features were lost on them. What they needed was to be trained on how to build a digital marketing foundation. Delegation The CPO had fallen into another common trap, where he had failed to delegate as the company grew, and had become a critical bottleneck in the product development process. He had the product vision in his mind, but was unable to articulate it to the team in sufficient technical detail for them to execute. He became the go-to person for everything, a critical bottleneck. He couldn’t get down to the level of detail required to drive a product of this scale, so there was serious requirements churn. He also suffered from extreme burnout. Co-Founder Conflict All of this stress and struggle with growth created a rift between the co-founders. With different goals and vision for the company, they undermined one another. The misalignment between areas of the business created gridlock. There was an inevitable split and fire sale of the company.
Solution
Product-Market Fit The first order of business was to talk to customers and understand their challenges with the platform. I coached the CPO on how to stand up a program to gather customer feedback and perform interviews. We quickly discovered that customers didn't care about advanced features, because they didn't understand how to use the platform. We needed to invest in training and customer success. We began by doing a case study with their most successful customers. We learned what made them successful, everything from the content of an email, to structure, scheduling, voice, and segmentation. We created an online training course, eCommerce Email Academy, to teach these methods to the novice digital marketers. We invested in highly trained, white-glove, 24/7 customer support to help customers maximize their success with the platform. Delegation With every client I coach, there is always a challenge with delegation. Executives at rapid growth companies always hold on to work for too long, because they believe they can do it best, and struggle with teaching others how to do it well. We began with Calendar Control, where we audited the CPO’s calendar and: Cancelled or delegated low-value tactical meetings Carved out regular time for high-value strategic work Themed days to minimize context switching Implemented a tool to only allow certain types of meetings to be scheduled at certain times We then performed a Skill Mapping exercise, where we mapped the skill and focus of the executive against the needs of the business. We identified areas for growth and areas for delegation. In the Areas for Growth, we developed a 3, 6, and 12-month plan for his personal development. We began with simply blocking out time for each activity, so that he was focusing his time in proportion to the value. We then developed a set of SMART Goals for each item, and tracked his progress and KPIs over time. In the Areas for Delegation, we created a Process Inventory, then one-by-one delegated small pieces of the puzzle, until entire workflows were delegated. To ensure a successful handoff, we established metrics and reporting so that he would know that the process was being executed well. We created a Hiring Strategy for the new product team, and brought in experienced product managers, analysts, UX researchers, and designers. We created tight feedback loops between customer success, product, and development, so that the needs of the customers were being effectively realized in the product. All of this required months of deep leadership coaching and training for the CPO, which was the main focus of our engagement. Co-Founder Conflict To overcome the tension and deep-seeded resentment, we first had to dig into root causes. It turned out that the founders had a fundamentally different level of risk tolerance, and different level of belief in the future success of the company. First and foremost, we created a set of shared Principles, Values, and a Code of Conduct so that each executive behaved in a respectful and empathetic manner. We structured a partial buyout to mitigate risk for one (more cash, less equity), and provide upside to the other (less cash, more equity).
Results
Our results were transformative. Through better engagement with customers and a more effective product team, the company more than tripled engagement and retention. In 2018, 3 Billion emails were sent, but in 2020, 10.4 Billion emails were sent, and customers generated over $150M in revenue. We built a small but mighty product team, allowing the CPO to focus on strategy and innovation, resulting in better overall adoption and engagement of new features. The development team reported more clarity of direction, a better understanding of the product, and lower stress. We successfully diffused tension between the founders, resulting in better alignment across the company, and avoiding a catastrophic split. The relationships still aren’t perfect, but it’s manageable. Overall, this was one of the most challenging, multi-faceted, and rewarding coaching engagements of my career.
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