""I kind of hid her. People didn't know about her. [But] they noticed a change. I started to get feedback essentially saying, 'Whoa. Courtney's shown up to meetings on time and she seems a little more relaxed.'""
— Courtney Kingston, Founder and CEO
The Challenge
As Founder and CEO of Kingston Family Vineyards, Courtney Kingston managed the importing, sales, and marketing for her family's multigenerational wine business — all while raising three daughters alongside her equally busy entrepreneur husband. With a 100-year-old farm and a vision that looked decades — generations — ahead, Courtney felt the weight of being indispensable everywhere at once.
The cracks began to show. She was missing pediatrician appointments, putting off tasks that truly mattered, and couldn't keep her head above water. Her brother's pointed observation stung:
"You can't be a CEO and not read all your emails."But Courtney resisted, convinced she couldn't justify the cost of help.
When she brought her struggles to her female leadership group at Stanford — women she had shared professional and personal challenges with for eight years — they echoed the same message. Still, she pushed back:
"No, I can't afford that. I don't need that."She was certain her email needed to stay in her own voice and that spending on herself didn't feel right for a business still reinvesting every dollar into its next phase. It was only when the group held her accountable — insisting she commit to at least six months — that Courtney finally opened the door to getting help.
The Solution
Through BELAY, Courtney was paired with Virtual Assistant Erica for 45 hours a month. From the start, the relationship felt natural. Erica had experience with family businesses, spoke Spanish, and shared a similar life stage and personality. Courtney — a self-described Type-2 Enneagram who values connection and transparency — felt at ease almost immediately.
The partnership began with email management, though Courtney had lingering reservations about someone else speaking in her voice. Over time, Erica earned her full confidence. As Erica explains:
"When I learned Courtney's voice, it became even easier. I knew [when to use] my voice and [when to use] her voice."
From there, the scope expanded — from email to calendar management and well beyond. Erica learned to build breathing room into Courtney's schedule, protecting time between meetings and carving out space for personal needs. Courtney credited BELAY's onboarding advice as the foundation of their success:
"I remember the number-one piece of advice was [about] the importance of trust. If I don't fully trust, then Erica can't do all the things I really need her to do."
""My job is to meet the client where they are. What Courtney and I have in common is that we have the three kiddos and we all have a flurry of activities and things going on. So I think I'm able to really understand where she's coming from.""
— Courtney Kingston, Founder and CEOThe Impact
The results were visible before Courtney even announced she had help. She initially kept the partnership quiet — but colleagues noticed the change on their own.
"I started to get feedback essentially saying, 'Whoa. Courtney's shown up to meetings on time and she seems a little more relaxed.'"
Erica's support went well beyond logistics. She began proactively anticipating Courtney's needs — including holding back a weekend email to give her space to process before hitting send. The gesture stopped Courtney in her tracks:
"That stopped me in my tracks. Erica not only knew my strengths, but she could even anticipate my blind spots!"
With her calendar managed and her inbox under control, Courtney gained something she hadn't had in years: room to breathe. She could be more present for her family, protect time for herself, and lead her business with greater clarity. The partnership that began as a reluctant six-month experiment became an indispensable part of how she leads. As Courtney simply put it:
"It's just trusting in each other. It's as simple as that."