Fashionably Late is proud to release our Female Founder Series. Each week in April, Fashionably Late will feature a different female founder. From the tech space to the wellness industry, our four business leaders are eager to share their journey, advice, and fun personal tidbits. This week we have Caroline McCaffery, Co-Founder & CEO Her story is one about following your passions, using them to drive your professional trajectory, and trusting yourself to transform your career at any point. Driven by her desire to constantly learn and solve problems, Caroline has met job, career, and industry shifts with an openness integral for her success of founding her own company. Her adaptability and excitement for online privacy, her company’s sector, will empower you to take the risks necessary for finding professional fulfillment.
Starting her career when the .com bubble burst, Caroline has always been intrigued by and worked in the tech space. A lawyer by training, Caroline’s first role as an attorney was at Gunderson Dettmer, a firm that works with startups in the tech and life sciences spaces. As a Corporate Securities Attorney, she aided startups with financing, often debt and equity, as well as mergers and acquisitions. Spending almost ten years with the firm, Caroline was able to get a lot of experience working with startups.
Excited and challenged by supporting startups, in 2011, Caroline transitioned into her first in-house role. Still eager to work in tech, she joined the marketing and advertising automation company, Sailthru. She notes that she started this position at a transition moment in the internet space, as big data emerged as the leading technology. As Sailthru processed online users’ data, Caroline recognized a problem: how could users ensure how/if their digital information would be protected? Following her budding curiosity in data while still staying in her industry of expertise (tech), Caroline shifted her focus as an attorney to commercial and privacy.
These new interests in data security and privacy led her to seek another general counsel role at another tech start-up, Clarifai. She entered the AI facial recognition company in its early stages. She found her role morphing outside its job description, as she also supported the company’s strategy and operations. By leveraging what she learned about startups while at a firm and as Sailthru’s privacy-focused general counsel, as well as embracing her intuition and openness, Caroline became the VP of Business Affairs while retaining her General Counsel title.
Continuing to focus on privacy law while tackling unfamiliar strategy-based challenges as VP of Business Affairs gave her “a taste of the entrepreneurial side of [her]self.” As the “type of person who loves to constantly learn new things,” she recognized that new challenges and new opportunities to develop solutions fuel her drive.
In addition to expanding her hard skills while at Clarifai, Caroline also gained a much deeper understanding of AI and cybersecurity, contributing to her growing passion for technology and data privacy. From there, she developed a hunger to create tech to ameliorate issues affecting users’ online protections. After meeting George Rosamond, her future co-founder and CTO, a conversation about anonymity online evolved into a problem they were determined to solve. The security questionnaires that companies send to potential vendors who process online information can 1000+ questions long, plaguing vendors. These are sent pre-sale and in some cases the vendor will spend hours to complete the questionnaire without even landing a sale!
Since she and George clearly identified the challenge they wanted to solve and through discussions, discovered potential software solutions, it seemed as if the natural next step would be to start their B2B SAAS company, ClearOPS. They even had large goals for ClearOPS working as a “wheel in the spokes” type of mode, in which their services can connect other businesses and ultimately improve privacy communications. George was ready to commit full-time to transition their idea into an executed product. But starting a business is never linear. For Caroline, first came her “professional identity crisis.”
Caroline wavered between staying at the job she loved, finding a new GC role, or following her dream to start ClearOPS. She asked, “Am I a lawyer? Am I capable of being a COO? .Or am I a founder?” As a lawyer, she is trained to circumvent risks. Pursuing a career marked by innumerous risks seemed like the choice to avoid. Even when she conducted extensive research to evaluate if there was a market for their security/privacy product- there was- she was still uncertain. Until one day at breakfast, she got the push needed to “take a leap of faith” to begin identifying as a founder.
Listen to Caroline’s journey of founding and becoming ClearOPS CEO and you will realize that you do not have to be just one career label, as she constantly adapted to execute whatever work she wanted to get done. You will be motivated by how she and George completely pivoted their initial model after taking potential investors’ “fair critical feedback.” Despite ClearOPS losing its biggest deal during the pandemic, as CEO, Caroline again adjusted to the circumstance, conducting business so that their company finished the year with a product on the market and multiple customers. ClearOPS’ founding story is one of balancing the line between following your passions and adapting to meet the needs of your business, ever-evolving market, and customers’ needs. Both Caroline and ClearOPS continue to meet goals, providing the team confidence that ClearOPS will be a central player in the growing privacy tech space.
A recurring theme in Caroline’s narrative is that a passion for learning, then trying new things offers fulfillment and fuels success.
Topics covered in this episode:
- Why it is in a startup’s best interest to be proactive and hire a lawyer early
- Insight into evolutions within the internet space, including the emergence of big data and privacy
- A lawyer’s take on overcoming and managing risk
- The different lessons learned from working at a firm, as an in-house GC, and as a founder
- The importance of leaning on your support network and only taking “fair critical feedback”
- Why execution is more imperative than conjuring an idea
Links:
https://www.clearops.io/