Caroline Jennings expected to work in science or therapy after studying psychology and neuroscience. She later moved into user experience design, then found an unexpected business opportunity while helping her father with his dental practice’s online presence.
In this Founder Factor episode, Jennings moves from the host’s chair to the guest’s. She describes the early days of Word of Web, learning business fundamentals as she went, finding clients despite anxiety about selling, and building a team that could deliver without every task depending on her. The conversation also explores how her definition of success changed once she achieved the flexibility she originally wanted.
What you'll learn.
- A small project for someone you know can reveal demand, but running the business still requires deliberate learning.
- Write down the service process so knowledge can move beyond the founder.
- A consistent team can make delegation and quality more dependable than assembling every project from scratch.
- Clear client expectations and asking for help can support a more sustainable working life.
A family conversation reveals an unmet need.
Jennings began her career in user experience design and worked as a product director at a health technology company. During that period, her father mentioned that fewer new patients were coming into his dental practice. When she asked about the website, she learned that he did not have one.
He had relied on word of mouth. Her response about the importance of the web supplied the name for the business she would later build. She made his website as a side project, enjoyed the work, and asked friends and relatives whether they needed help too.
She recalls making about five websites without charging during that first year. Those projects gave her experience and helped her recognize a need. They also show how the business developed through a sequence of practical opportunities, rather than a fully formed plan to become an entrepreneur.
An intended six-month experiment becomes full-time work.
Jennings left her job in January 2020. Her original plan was to run Word of Web for several months while applying for another position, then move to New York City. The pandemic changed that plan.
She saw businesses struggling with inadequate websites and a growing need for online sales. The work began to feel like something she should continue. What had looked like a temporary step became the business she committed to developing.
Her account avoids the idea of one perfect launch moment. She made a decision with the information she had, then changed direction as circumstances and customer needs became clearer.
Learn the business tasks one question at a time.
Jennings says she did not know how to handle many of the practical requirements of starting a business. She researched unfamiliar topics and built a growing checklist, including business registration and insurance questions. Each answer revealed another item to investigate.
She estimates that it took about six months to feel that the basic foundation was in place. The process suited a habit she had developed earlier: teaching herself new skills, including user experience design through an online course.
Finding customers required a different kind of learning. She visited local businesses, tracked new business registrations, and introduced herself in person. The first visit made her so nervous that she called her mother for encouragement before going inside. She says that business later became a customer. Word of mouth remained an important source of work, even for a company named around the web.
Decide whether the business should depend on you.
At first, Jennings priced work much like a freelancer, estimating hours and multiplying them by a rate. As demand grew, she began to distinguish between selling her own time and building an organization that could exist beyond her.
That shift required processes, documentation, and a different view of responsibility. She wanted the knowledge about how to deliver a project to live somewhere other than her head.
Her priorities also widened. Personal flexibility had been attractive at the start. With a remote team and ongoing client relationships, she began thinking more about the lives the business helped support. In the interview, she describes responsibility for colleagues’ pay, working arrangements, and enjoyment of their work as central concerns.
Build trust in a team through real responsibility.
Jennings’s first contractor hire came when she had more projects than she could handle. She describes the decision as a response to overload, with less planning than she would recommend in hindsight. Handing over work was difficult because the business felt personal.
The designer did excellent work, which helped her see that delegation could improve the result. She then experimented with selecting a different mix of contractors for each project.
Over time, she found that approach inefficient and harder to manage consistently. A core team gave her more confidence in the quality of the work and in who could take responsibility for it. Her account suggests that delegation improves when the founder can rely on established working relationships and a shared process.
Turn a service into a clear sequence of commitments.
Jennings uses the phrase productizing a service to describe making the buying and delivery process more consistent. In practical terms, the client knows what the engagement includes, how it starts, and which deliverables to expect.
At the time of the interview, Word of Web began projects with a two-week blueprint phase at a set price. A two-hour conversation covered the client’s goals, budget, and business, followed by planning deliverables that guided the website work. She compares this to an architect preparing a plan before construction.
The example shows how a service can become easier to explain without making every client’s website identical. The repeatable part is the sequence of decisions and deliverables. Jennings says the team had spent several years developing that structure and was then focused on reaching more of the clients it worked with well.
Set boundaries and use a working rhythm that fits.
Having a team helped Jennings create some separation from the business. Knowing colleagues could handle the work made taking time away feel possible. She also became clearer with clients about when calls would happen, rather than assuming she needed to be available at every hour.
She describes recent burnout, so the conversation does not present those changes as a permanent solution to every pressure. Part of the adjustment was recognizing when she needed rest and when a day required a less demanding type of work.
Her task system separates easier administrative work from harder work that needs more energy. Strict calendar blocking had been less useful: when incoming email or a task took longer than expected, the schedule itself created anxiety. She still wanted structure, but preferred checking how her time matched her priorities across a week. The useful lesson is to evaluate a method by whether it helps the person doing the work.
Let your reasons for doing the work develop.
Jennings describes reaching the flexibility she wanted and then asking what she wanted to do with it. Her answer increasingly involved other people: supporting her team, helping clients, and contributing to causes she cared about.
Mental health work was especially meaningful to her. She mentions projects involving a crisis-line website and a mental health platform for veterans. Those examples connect her earlier interests in psychology with the work her business could take on.
Her advice to another prospective founder is to begin with a practical action rather than wait for certainty. Planning matters, but she says waiting for an unmistakable sign can delay all progress.
Asked for the founder factor, she chooses knowing when to ask for help. That may mean calling a friend, seeking advice from a mentor, or getting personal support. She sees caring for her own well-being as connected to her ability to run the company. The role does not require solving every problem alone.
Word of Web grew through customer work, self-directed learning, and repeated changes to how Jennings saw her role. A project for her father became a business, and the business became a shared responsibility with a team.
For someone making the same transition, her experience points to practical work: define the service, document how it is delivered, give capable people responsibility, and keep revisiting what a successful business should make possible in your life.
