Sarah Jenkins and the trouble with too many tools

Sarah Jenkins had a familiar complaint about running an online business: there were too many things to connect. A page lived in one place, an email campaign in another, and the business owner was expected to make the introductions. Software promised to save time. Quite a lot of that time could disappear into making the software cooperate.

Jenkins experienced that problem as a seller. She would later help run a company offering a solution. Genesis Digital, which she co-founded, became the business behind Kartra, WebinarJam and EverWebinar. In 2019 she became its CEO. In April 2024 she handed that job to Darren Hakeman and continued on the Board of Managers.

Between those titles sits a working life concerned with the unglamorous parts of entrepreneurship. Finding a customer. Sending the right message. Collecting payment. Making sure the person who bought something can actually get it. A grand idea is pleasant company. It is less helpful when the checkout refuses to speak to the mailing list.

The customer’s side of the screen

The connection between Jenkins’s own experience and her products is unusually direct. She has described starting with little money, reinvesting as she went, and feeling frustrated by the collection of tools needed to sell her products. Separate subscriptions brought separate complications. Kartra was the attempt to put the necessary functions into a connected system.

Consider the sequence from a buyer’s side. Someone discovers a business, watches a presentation, decides to pay, and expects access to a product or membership. The seller must keep that sequence moving. Each stage may be simple enough on its own. The difficulty comes when information has to travel between them.

That is the territory Jenkins’s company chose. WebinarJam handles live presentations. EverWebinar supports automated webinars. Kartra brings marketing and commerce functions together. The products address different parts of the same working day, from getting attention to serving the person who has paid.

Genesis Digital’s early history follows that practical progression. The company was founded in 2013; its first iteration of WebinarJam launched in 2014. EverWebinar followed in 2015, and Kartra was publicly released in 2018. The team used its own products, including Kartra for business operations and WebinarJam for customer questions and demonstrations.

For Jenkins, this made the customer more than an imagined figure in a marketing plan. She had occupied that seat. Her product argument begins with the expense and inconvenience she had already encountered. It is an accessible explanation for a software company: the people selling the remedy had spent time wrestling with the problem.

Her attention to friction could extend to quite small requests. She recalled being pleased when feedback on a webinar feature included a desire for dark mode. After the work of development, a complaint about the color scheme could feel reassuringly manageable. Sometimes the customer’s next wish is simply easier on the eyes.

A business education outside the classroom

Jenkins’s route into leadership included homeschooling, early selling and work inside the business. She grew up near Detroit. At 12, she tried to attract babysitting customers by distributing flyers with a free first hour. The offer was small; the idea behind it was recognizably commercial. Give someone a reason to try the service.

Later came experience in online marketing and a role close to the company’s numbers. Her career record includes bookkeeping at Genesis Digital before she became CEO. It is a useful detail beside the more visible founder title. A company’s ambitions look rather different when they have to fit inside accounts.

She took the chief executive role in 2019 without a college or business degree. Her responsibilities included finance, daily operations, management and company culture. There was plenty to learn, and she has described seeking help from people whose knowledge complemented her own.

In 2020, Genesis Digital ranked 1,854 on the Inc. 5000, reporting 228.74 percent growth over the ranking’s measurement period. The milestone belonged to a company with more than 100 people working around the world. Jenkins was leading an organization whose daily reality had moved a considerable distance from its kitchen-table beginnings.

There is a temptation to make an unconventional education explain everything that follows. Jenkins’s career deserves a more practical reading. She accumulated experience, took on responsibilities and learned from other people. The early flyer and the later accounts both involved attending to what a business needs before it can do the exciting part.

A company without a corridor

The organization she led was fully remote. Geography therefore changed the ordinary mechanics of management. A question could not always be answered by walking to someone’s desk. A written request had to carry enough information, and enough of the right tone, to stand on its own.

Jenkins has discussed the effort involved in making that tone clear. She also puts integrity high on her list when choosing people to work with. “Integrity is number one,” she has said. Technical ability matters; so does the conduct of the person exercising it.

Her approach to leadership also draws on being a mother of five. She has publicly linked her management philosophy with parenting, emphasizing a workplace in which people feel valued and able to contribute. In her writing about families and businesses, she has explored vulnerability, transparency and empathy as qualities with a place in working relationships.

Those words acquire practical weight in a distributed company. Employees have to ask questions, disclose difficulties and trust that an unfamiliar tone in a message does not necessarily signal a crisis. A remote team still has relationships. They simply require attention without the assistance of a shared kettle.

“My biggest takeaway is to be open and coachable.”

Sarah Jenkins, on media training

Jenkins has applied the learning argument to herself. Describing media coaching, she acknowledged trying exercises outside her comfort zone and becoming more receptive to advice. The detail is appealing because it is ordinary. Experience at running a company does not automatically make a person practiced at every new situation.

The same distinction helps explain her leadership story. Having responsibility does not require pretending to possess every skill. It requires making decisions about where other people’s experience can improve the work. Her public thanks to colleagues suggest she understands a company as a shared undertaking.

The microphone changes hands

In May 2023, Jenkins and AJ Roberts launched Paid To Create. The opening episode made her the guest, with Roberts asking the questions. It was a tidy introduction to a show about entrepreneurship: let one of the hosts explain the working life she was bringing to the conversation.

When she announced the podcast, Jenkins emphasized integrity, quality and female leadership. She addressed women starting companies and people balancing new businesses with family responsibilities. The invitation was rooted in experience rather than a promise that everyone could follow an identical route.

The show’s subsequent subjects were similarly close to the business owner’s desk: marketing messages, advertising, customer relationships and managing teams. A November 2024 question-and-answer episode covered trust, advertisements and remote management. A January 2025 installment considered marketing and branding predictions for the year ahead.

The microphone gave Jenkins another way to work on the problems her software addressed. A platform can provide the mechanism for reaching customers. A conversation can help a business owner decide what to say, what to offer, or which question to ask next. Both depend on understanding the person doing the work.

Leaving the chair, keeping a seat

The next formal change came on April 2, 2024, when Darren Hakeman succeeded Jenkins as CEO. He had served as president since March 2022. Jenkins remained on the Board of Managers, retaining a place in the company’s governance as operating leadership passed to him.

Hakeman’s introduction included a thank-you for her years of guidance and continuing support. Genesis Digital then described a business with more than 25,000 customers. That figure belongs to the handover period; it marks the scale of the operation at that point in her career.

Earlier that year, Jenkins had described an ambition for AI to help users choose effective marketing funnels. It was a proposed direction, with the same practical concern underneath: a seller still has to decide how to use the tools. Giving someone a platform leaves room for another kind of help.

The professional connections continued beyond the announcement. In May 2025, executive chairman Vik Verma shared photographs from a San Diego meeting with Jenkins and general counsel Grant Teeple. He identified her as a co-founder and board member, and included fellow co-founder Hector Yague and Hakeman in his account of the company’s leadership.

It is a quieter scene than a product launch: colleagues meeting, a photograph near the water, work continuing under a changed arrangement. Yet it belongs in the story. A founder’s relationship with a company can outlast the job of running its daily operations.

Jenkins’s career has moved from selling and bookkeeping to executive decisions, podcast conversations and board responsibilities. The thread is the business owner with something to offer and a list of practical jobs standing between the offer and a sale. She knows that list from experience. There is usually another item on it.