About Ashley
Ashley Tocco is an accomplished executive with over a decade of leadership experience, specializing in scaling and optimizing businesses. With a diverse background across operations, customer support, product management, HR, engineering, and sales, Ashley brings a comprehensive understanding of how to drive business growth and operational efficiency.
Ashley began her leadership career in 2011 and rose to prominence in 2018 when she joined Clipboard Health as employee number 3 and the company’s first executive. During her time there, she played a key role in growing the company by 20X in revenue, scaling from 3 to 250 employees in just two years, and achieving profitability within the first year. Ashley’s leadership set the path for Clipboard Health to reach unicorn status, valued at over $1 billion in 2022. As General Manager, she built and optimized teams from the ground up, establishing operational systems that set the foundation for long-term success.
After her success at Clipboard Health, Ashley served as VP of Operations at Karat, where she oversaw the development of critical operational functions, including customer support, risk management, and people operations. She was also instrumental in launching new ventures in taxes and booking, further strengthening her expertise in scaling complex operations, aiding in the raise of over 100M in funding.
In addition to her professional achievements, Ashley has built a successful real estate portfolio with Monarch Investment Group, focusing on commercial properties in San Diego. In 2023, she expanded into the short-term rental market with her first property in Texas.
Ashley is currently focused on acquiring a high-potential business that aligns with her expertise in operational optimization and growth. While she has a strong interest in the med spa industry, she is open to exploring profitable business opportunities across various sectors where she can leverage her skills to drive sustainable growth.
The Journey
Ashley’s journey into business acquisition wasn’t a straight path—it was shaped by the lessons learned from overcoming challenges, embracing change, and seizing opportunities along the way.
Her career began with a strong foundation in leadership, but it wasn’t until she joined Clipboard Health in 2018 that her vision for scaling businesses truly took shape. At that moment, she saw firsthand how a small, driven team could grow rapidly, but also how crucial it was to adapt to fast-paced, evolving demands. Early on, Ashley discovered that leadership wasn’t just about making decisions—it was about creating systems that would allow businesses to thrive long after those decisions were made.
The experience of helping scale Clipboard Health taught her the importance of patience, flexibility, and strategy. While the growth was exciting, it wasn’t without its obstacles. From managing a rapidly expanding team to refining operational processes, each hurdle helped Ashley develop a deep understanding of how businesses need to be structured to sustain growth and profitability. She realized that success wasn’t just about numbers—it was about creating a culture of continuous improvement and adaptability.
After seeing the transformative power of scaling operations and building high-performing teams, Ashley’s interest in real estate investing naturally followed. Alongside her husband, she dove into commercial real estate and eventually took on her first short-term rental property. These ventures deepened her appreciation for identifying growth potential, whether it was a building or a business. Both experiences have shaped her belief that with the right systems, strategic guidance, and a focus on long-term value, any business can be elevated.
Now, Ashley is channeling those experiences into her next big venture—business acquisition. She’s not just looking to acquire; she’s looking to grow, optimize, and create lasting impact. It’s about bringing the same principles of operational excellence and strategic leadership to businesses in need of direction and growth. Whether it’s a med spa or another profitable venture, Ashley’s approach is rooted in a deep understanding of the power of systems, innovation, and vision.
For Ashley, the journey isn’t just about expanding a portfolio—it’s about finding businesses with the potential to be more than they are today and working to turn that potential into reality.
Business Specifications
“I’m interested in acquiring profitable businesses with a history of steady growth and a solid foundation. Ideally, these businesses have already established themselves but still have significant room for expansion. My focus is on opportunities where I can apply my experience to streamline operations, drive further growth, and create long-term value.”