Cloverleaf: Offering Customized Coaching Tools In A $4+ Billion Market

By Amit Chowdhry • Jan 1, 2024

Cloverleaf is a technology platform that is bringing automated team coaching to the entire enterprise through real-time, customized coaching in the tools employees use every day (calendar, email, and Slack / Microsoft Teams). The result is better collaboration, improved employee relationships, and a more engaged workforce. Pulse 2.0 interviewed Cloverleaf CEO Darrin Murriner to learn more about the company.

Darrin Murriner

Along with serving as the co-founder and CEO, Murriner is also the author of Corporate Bravery, a book focused on helping leaders avoid fear-based decision-making.

Formation Of Cloverleaf

How did the idea for Cloverleaf come together? Murriner shared:

“I settled into a career path in college and spent 15 years in various large companies, climbing the corporate ladder. I had always noticed that my need to build existed even inside these large organizations, but I wouldn’t have called myself an entrepreneur.”

“I eventually got the courage to step out of the corporate career path and bet on myself. I decided I wanted to build something from the ground up but didn’t quite know what that would be. As I was deciding to leave the corporate world behind I started writing a book entitled Corporate Bravery that took some of the key lessons I learned in my career about building strong cultures. This turned out to be a great way to organize my thoughts about what would eventually become Cloverleaf.”

Favorite Memory

What has been Murriner’s favorite memory working for the company so far? Murriner reflected:

“There are so many to choose from, but a few stand out. 2023 has been a great year for Cloverleaf and that has been punctuated by being named to the Inc 5000 of the fastest growing private companies – #486 to be exact. We have also become partners of companies such as Workday and Gallup, which has helped validate all the hard work our team has put in the past few years.”

Core Products

What are Cloverleaf’s core products and features? Murriner explained:

“Cloverleaf is unique in a few ways. The first is that we are a single platform and interface for accessing behavioral assessments in a Netflix-style subscription model. Secondly, Cloverleaf uses that behavioral data to provide customized coaching in the tools that employees use every day such as email, calendar, and Microsoft Teams or Slack.”

“Finally, we serve that coaching up in a team context so the individual user doesn’t just get coaching on themselves but on the people they interact with on a daily basis. The result is more self-awareness, better work relationships, improved communication, more effective collaboration, and ultimately improved team performance.”

Challenges Faced

Has Murriner faced any bottlenecks in his sector of work recently? Murriner acknowledged:

“Because we are a software company, we have avoided any issues that other industries have faced with supply chain disruptions and the like. We are only limited by our own creativity and ability to execute. As such a lot of our internal effort is focused on learning and collaborating as quickly and effectively as possible. We invest heavily in our culture and social connections to ensure we are iterating on and solving problems as quickly as possible.”

Evolution Of Cloverleaf’s Technology

How has the company’s technology evolved since launching? Murriner noted:

“Our product has evolved a ton because we are regularly incorporating new technologies. A great example of this is the explosion in the availability of accessible Artificial Intelligence (AI) tools. We have been able to incorporate AI in a responsible way that protects user privacy and transparency while increasing the usefulness of our automated coaching to users by making it more relevant and accessible.”

Significant Milestones

What have been some of Cloverleaf’s most significant milestones? Murriner cited:

“We have crossed quite a few milestones in the past few years. I distinctly remember passing the first million dollars in revenue – only 9% of businesses reach that threshold. I was also excited when we passed five years in business – nearly half of businesses reached that milestone. And raising a successful Series A round of funding was also another great validation point – less than 25% of startups reach that milestone.”

Customer Success Stories

After asking Murriner about customer success stories, he highlighted:

“We do regular customer interviews to make sure we are building products and features that help solve problems that our customers face every day. Recently, one of our user experience designers spoke with a customer who had the following story. This person described themselves as extremely Type A and very detail-oriented but shared that they struggle with ‘soft skills,’ especially reading social cues or body language that most people pick up on immediately. This person mentioned that sometimes people misinterpret their directness as rudeness or coldness. Cloverleaf has helped them learn how to better communicate with teammates effectively, determine which colleagues would prefer to have more interpersonal chat before work, or get more ‘soft’ touches before hard subjects.”

“Cloverleaf has already become an integral part of their daily routine — the first thing this person does every morning is open their daily coaching email to start the day. It has been so helpful having dashboards so they can learn about new colleagues before they meet for the first time and be prepared to know how to best relate and communicate with them.”

Total Addressable Market

What total addressable market (TAM) size is the company pursuing? Murriner assessed:

“We sit at an interesting intersection between the behavioral assessment market, which by some estimates is as large as $4 billion, and the business coaching market which is $13 billion annually. While we sit inside of both of these markets we are also expanding the overall size of that market. As an example, today, coaching is mostly only accessible to the top 2-5% of employees.”

“It is typically reserved for the most senior leaders in the organization. However, front-line employees and new managers or supervisors can benefit the company the most by gaining access to coaching. In the same way wearables helped expand the overall size of the fitness market, we are helping expand the overall size of the coaching market.”

Differentiation From The Competition

What differentiates the company from its competition? Murriner affirmed:

“Cloverleaf is the first technology with a focus on the common behavioral challenges in the workplace. Most employees and leaders have come to accept that not liking your coworkers or dealing with that difficult manager is just a fact of life. The reality is most of the difficult interpersonal challenges you face in the workplace is the result of a clear misunderstanding. We all work differently, and what we need to be successful with the work we have been hired to do is different from the other people around us. How we communicate and are motivated is vastly different from person to person.”

“There is nothing wrong with these differences, but having a clear awareness of these differences and how to navigate them effectively is critical to business success. Cloverleaf teaches self-awareness and emotional intelligence and there are very few solutions on the market that can do that.”

Future Goals

What are some of the company’s future goals? Murriner pointed out:

“When confronted with this question, I often hear other business owners just say more. ‘We want to increase x by y, and we want to reach another million or billion people.’ Just reaching the next incremental numerical milestone isn’t super rewarding. Instead, my cofounder and I have just been focused on building a great product and a great culture. Our mission is to unleash people to do their best work, and we believe we can accomplish that when every team is a thriving team. That is the ultimate measure of success for Cloverleaf.”

Additional Thoughts

Any other topics to discuss? Murriner concluded:

“I’d love to touch upon the significance of prioritizing a human-centered leadership approach in today’s fast-paced corporate environment. I believe the best way to improve performance and effectiveness is by better understanding human behavior and dynamics. At Cloverleaf, we deeply believe in putting the human at the center of everything we do. It’s the people within every organization and their unique characteristics that truly matter. Our commitment to empowering and understanding individuals is foundational to our success and will continue to guide our product in the future.”

Want To Buy Darrin Murriner’s Book? You can find it below:

Disclosure: Pulse 2.0 may receive a commission for the purchase of Murriner’s book via Amazon.