Cailyn Benson
Dedicated professional nanny with a passion for creating nurturing, engaging environments where children can grow with confidence and curiosity.
About Cailyn
I was born and raised in Portland, Oregon, a place that shaped my love for nature, creativity, and community. Growing up here instilled in me a deep appreciation for curiosity, connection, and the importance of nurturing children as whole individuals.
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My first instinct is always to stay calm and present. Children often borrow the emotional energy of the adult around them, so I focus on being a steady presence. Instead of reacting quickly to the behavior, I try to understand what’s underneath it.
When children feel safe and understood, they’re much more able to regulate and move forward. I guide them through their feelings while still holding clear and consistent boundaries. Over time, this helps children learn that emotions are safe to express and that they are capable of working through them.
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For me, a meaningful day balances rhythm with curiosity. Having a gentle structure helps children feel grounded, but within that structure I love allowing space for exploration.
Many days include outdoor adventures, library visits, art projects, baking, reading, or simply noticing small things in the world around us. Some of the best moments come from slowing down and following a child’s curiosity.
Children don’t always need constant entertainment. Often they just need time, attention, and the freedom to imagine and explore.
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I see myself as both a nurturing caregiver and a supportive member of the household team. My goal is always to align with the parents’ values and create consistency for the children.
Clear communication and mutual respect are very important to me. When the adults in a child’s life work together with trust and shared understanding, children feel safe and supported.
I take pride in being someone families can rely on, someone who brings calm, thoughtfulness, and genuine care into the home each day.
Approach to Care
Experience
Infant through teenage care
Multi-child & flexible scheduling experience
Household management & travel support
Developmentally aligned activities & routines
CPR, First Aid, & water safety certified
What Families Have To Say
“We absolutely LOVE Cailyn! She consistently goes above and beyond for our family. Our son is always thrilled to see her — his face lights up every time she walks through the door!”
“She has a warm, empathetic energy and is a natural with kids. Our little one took to her right away. She even helped us get started with solids!”
“She works independently, autonomously, and upholds the highest standards of care… She has never missed a day of work, shows up on time, and is always so flexible with our crazy schedules.”
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It is with complete confidence and wholehearted enthusiasm that I recommend Cailyn as a nanny and caregiver. She has been nothing short of extraordinary for our family, and there isn’t a single piece of feedback I could give that isn’t positive.
From the very beginning, Cailyn was punctual, proactive, and remarkably respectful of our household values and routines. She took the time to ask detailed questions about how we operate—everything from parenting philosophies to where we keep our spoons—and she adapted seamlessly. She welcomed feedback with such grace, though truthfully, we never needed to offer much. She required no coaching, no redirection—she simply understood and aligned with our needs and values from day one.
As a family who values a constructivist and emotionally attuned parenting approach, we were astounded by Cailyn’s natural alignment with our methods. As a therapist myself, I was consistently in awe of her emotional intelligence, her thoughtful communication style, and her ability to navigate difficult conversations with maturity and ease. She didn’t just support our children—she supported us as parents, helping us work together more cohesively and compassionately.
Cailyn was deeply attuned to our children’s needs, adapting gracefully to every developmental shift and transition. She cared for our older child during the exhausting post-school hours, managing transitions, meltdowns, and overstimulation with patience and presence. She also supported our younger child through infancy, sleep training, nap transitions, teething—you name it. She kept us informed with respectful observations while giving us the space to explore and lead with our own instincts.
Beyond daily care, Cailyn was incredibly proactive: planning enriching activities around Portland, managing school lunch prep, rotating and consigning outgrown clothes, tidying and organizing toys, handling laundry, and always cleaning up after meals or family messes (even the ones we hadn’t gotten around to ourselves). She gave us ample notice for planned time off, was dependable in every way, and consistently showed up with warmth, intention, and love.
One of the most remarkable things about having Cailyn in our lives was the deep sense of peace she brought us as parents. We never once questioned our children’s wellbeing or safety when they were with her. Both my husband and I would often comment on how, when Cailyn was with our kids, we didn’t even think about them—not out of neglect, but because we trusted her that completely. There was an ease and nervous system calm she brought into our home that is truly rare. Knowing our children were in her care allowed us to focus on our work, our relationship, and our day-to-day life with full confidence and peace of mind.
Cailyn became an integral part of our family—so much so that we seriously explored the possibility of bringing her with us when we moved internationally. While we ultimately made a different decision due to logistical and financial factors, we remain deeply connected to her and hope to keep her in our lives for years to come. She is an exceptional caregiver, someone we trusted completely, and someone our children absolutely adored.
Simply put: hire her. Your home, your children, and your entire family system will be better for it. Warmly,
Stassi and Kevin
Parents of Emersyn (3 years) and Lively (17 months) Nastassia Betcher, Licensed Therapist
Kevin Boyle, MA
Let’s Work Together
I’d love to hear from families seeking thoughtful, dedicated childcare. Please use the form below to reach out with any questions or opportunities. I aim to respond promptly and look forward to connecting.
