“Flexibility Is Key” for This Working Mom and Lead Recruiter—Here’s Why

How do you make time for it all? As a lead recruiter at Upside and a busy mom of two, Crista Osher understands the challenges of juggling a career and parenthood. One of her keys to work-life harmony is the autonomy she has at Upside.

“Balance means having the flexibility to do your work whenever and however you need,” she tells Fairygodboss. “I’m present during key meetings and always complete my work on time; if I need to take my child to the doctor or pick them up from school, that’s OK. My leadership and manager trust me to get things done. This flexibility allows me to maintain a balance that, as a working mom, I wouldn’t be able to achieve otherwise.”

In addition to Upside’s flexible work environment, the company’s unlimited PTO has been particularly helpful when unexpected childcare issues arise. “I remember a previous job where I had to use precious vacation time when my child was sick, but at Upside, I don’t have to worry about that.” 

Alongside her work and family time, Osher knows how important it is to carve out space for self-care. When asked about her favorite ways to unwind, she says, “Yoga, long walks, working out, and watching mindless TV shows are my go-to stress relievers.” 

Here, we caught up with Osher to learn more about her daily routine, why she appreciates the company’s extensive benefits for parents, and her tips for integrating work and parenting.

First, can you tell us a bit about your job at Upside? What’s your current role, and how long have you been in this role?

I’m a lead recruiter at Upside and have been with the company for two and a half years. My role focuses on full-cycle recruiting, which means I bring top talent to our organization. We have a small, dynamic team, and as a result, each of us has a broad scope of responsibilities and an opportunity to make an impact. I am also involved with recruitment marketing and employer branding initiatives. 

Paint a picture of a typical day—what’s the first thing you do when you wake up and the last thing you do before you go to sleep?

The first thing I do when I wake up is check Slack. Since I work remotely for a geographically dispersed company, I check in early to confirm things are flowing smoothly, especially with our headquarters based on the East Coast. After that, I dive into getting my two kids—ages six and eight—out the door for school. The silver lining is that my afternoons are quiet, allowing me to focus. The last thing I do before bed is restorative yoga or watch one of my favorite TV shows while walking on the treadmill.

Attaining work-life integration can’t be done solo. What people, resources, and tools do you rely on to get it all done?

I appreciate the trust and flexibility my role offers. While we have four vibrant offices, we work to cultivate a flexible culture that has created a wonderful, seamless work-life balance for both in-office and remote team members like me. I also rely heavily on my husband to help balance childcare responsibilities.

What’s one misconception you think exists around work-life integration today?

One common misconception is that people who maintain a good work-life balance aren’t high performers or hard workers. A strong work-life blend keeps me from burning out and increases my engagement and productivity.

Let’s talk about your company’s culture. What’s your favorite aspect of it, and how does Upside help you achieve balance?

What I love most about our company is the incredible impact we all have. We’re in that perfect sweet spot where we’re large enough to offer stability, resources, and growth opportunities but small enough that everyone’s contribution truly matters without much red tape or hierarchy. One of the standout aspects of our culture is our commitment to transparency and open communication. Leadership is always clear about where the company is headed and encourages us to ask questions and provide feedback, creating an environment where everyone feels involved and empowered.

Additionally, the company strongly emphasizes learning and growth—whether through professional development opportunities or by encouraging us to take the time to learn new things. That mindset of continuous improvement keeps me motivated and engaged; I’m enabled to balance my career aspirations with my role as a parent.

What kinds of boundaries have you established to separate work and family time?

I minimize work on weekends. If something urgent comes up, I’ll hop on after my kids go to bed during the work week if needed, but weekends are reserved for family time. Weekdays can be hectic with school and activities, but weekends are sacred.

What type of programs does Upside offer to new and expectant parents? 

Upside offers tons of programs and partnerships to help support new and expectant parents  and is continuously evaluating and enhancing our benefits to better support working parents:

• Carrot Fertility: Access to doulas, midwives, and OB-GYN consultations, pregnancy-related counseling and education, and postpartum recovery and lactation support

• Modern Health platform: Resources and community support groups for new parents transitioning to working parenthood

• Paid parental leave: Competitive paid leave for new parents, allowing time to recover and bond with their child

• Lactation support: Access to private nursing rooms and breast milk shipping services for traveling employees

• Childcare assistance: Dependent Care FSA to help cover childcare costs

• Flexible work options: Hybrid and remote work opportunities to help balance work and family life

• Comprehensive healthcare coverage: Covers maternity care, prenatal and postpartum support, lactation consulting, and mental health resources for new and expecting parents covered under Upside’s medical plan

What are you especially good at as a mom? What about at work?

My superpower, both as a mom and at work, is empathy. I approach both my children and my work with care and understanding, always striving to help others grow and thrive. I empathize with my kids as they navigate their growth and support them in becoming kind, thoughtful people. This same empathy fuels my work, ensuring I stay connected and engaged with my team and candidates.

What’s your No. 1 tip for new parents navigating the delicate balance of working and parenting?

Give yourself grace. Things won’t always go as planned, and that’s okay! Enjoy the journey and focus on what you can control. It’s tough to juggle everything, but remember that you’re doing an amazing job, and your children will see you as their superhero.

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