Our client: An exclusive knowledge-sharing resource for C-suite leaders in high-growth companies. Over the years, it has evolved into a trusted platform where executives connect to find support, information, and advice to make better decisions.

For its first 8 years in business, the company existed as a primarily in-person endeavor. With the outbreak of the COVID-19 pandemic, however, the CEO and team had to pivot their business approach quickly to continue serving their loyal member base remotely in uncertain times.

Recognizing the need to bring on a strategic partner to help navigate and implement the organizational changes brought on by COVID, the CEO sought a Chief of Staff who could help strategize and execute the company’s transition.

“I needed a strong…strategist - an organized, operations-style person,” said the CEO. “Ultimately, the business didn’t need help commercially; it needed help operating.”

A friend introduced the CEO to Keziah Wonstolen, who was in the early stages of building Vannin Chief of Staff. She thoroughly broke down the role of a Chief of Staff for the CEO, highlighting what a CoS could do for the company from both a macro and micro perspective. She also demonstrated the potential benefits of hiring a fractional team member.

“Keziah was my entry into fractional work,” said the CEO. “I had this ‘aha moment.’ I realized this model could work for us and drive a lot of business, giving us access to talent I wrongly assumed a smaller business like Venwise wouldn’t have access to.”

Together, the CEO and Wonstolen crafted a fractional model that allowed Wonstolen to provide high-level support to Venwise in a cost-effective manner. Their partnership began with a thorough assessment of the company’s current operations, challenges, and future goals.

“At the time, we were building for an unknown future. We had to ask questions like: how malleable does this plan need to be? How can we drive value in this new world for our customers?” said the CEO. “I needed someone to brainstorm with me, conduct whiteboard sessions, then immediately make a project plan to guide us through that transition. That’s exactly what Keziah did.”

Core Operations

Wonstolen’s first task was to delve into core operations management, taking over the reins of day-to-day logistics and restructuring the finance team. She quickly became the de facto COO, providing leadership and guidance to the junior team while streamlining processes for greater efficiency.

“My team is amazing, but at the time they were largely junior staff,” said the CEO. “Because of [Keziah’s] experience, she pushed us into new territory operationally.”

Reinvention

As the company embarked on its journey of reinvention, Wonstolen served as the CEO’s sounding board for key ideas and initiatives. Drawing on her previous experiences, she brought new perspectives and insights to the table, helping to shape the company’s strategic direction.

From executing key initiatives to brainstorming new ideas, Wonstolen played a pivotal role in driving the company forward during this phase.

Special Projects

Additionally, Wonstolen took on several special projects aimed at refining Venwise’s operations and positioning the company for future growth.

She helped map out the rhythm of business, refining sprint planning protocols and guiding the team through those sprints. Her ability to balance day-to-day operations with long-term goal mapping proved invaluable in guiding the company through its transformation.

In spite of pandemic restrictions, the company continued to grow - which the CEO says would never have happened without their partnership with Vannin Chief of Staff. Wonstolen’s role became indispensable to the team’s success - and a seamless extension of the CEO’s reach.

“What’s interesting about Chief of Staff roles is that they’re a Swiss army knife,” said the CEO. “Some days it’s one thing, some days it’s another, and you need someone you can throw at all those problems. You need to trust that person, and trust that they’ll operate the way you would have operated or solved the problem.”

Knowing Wonstolen was carefully orchestrating the rhythm of business and keeping all projects on track, the CEO could focus on big-picture questions for the company. In other words, her expertise in operations and strategy enabled the CEO to work on the business rather than in the business - an invaluable gift for a busy operator.

When it came time to end their engagement, the company used Vannin Chief of Staff’s deep bench of talent to find their next CoS - someone possessing equal amounts of experience and rigor.

Now, Kaitlyn Boileau leads the charge as the company’s fractional Chief of Staff. With her at the helm, the company is embarking on new ventures, including international expansion, integration of AI, and professionalization of processes. Boileau also serves an integral role in the hiring process, recently finding a stellar replacement for the company’s finance partner.

Ultimately, the engagement with Vannin Chief of Staff has empowered the CEO to operate in their areas of strength, driving measurable impact and paving the way for a bright future for the company.

“That’s the biggest value add there is,” he said.