Taking That Conversation Led to Opportunity for Two Teachers Turned Calendly Team Members

Kristyn Bryan and Ashley Macken were once teachers in another life. Little did they know that the skills they learned while teaching would set them up to take on new opportunities in the tech industry. Learn about each of their journeys from classroom to corporate.

Kristyn Bryan has changed careers multiple times. In college, she studied English Literature only to find herself beginning her career as an event planner. “I just didn’t feel fulfilled in my job so I made the decision to go back to school to study education and ended up teaching elementary and middle school students. While I enjoyed teaching I also had a strong passion and interest in technology. So, guess what? I went back to school again! This time I went to study web development and studied to be a Full Stack Engineer.” 

During her time as a coder, Bryan found it to be isolating and missed the human element she had when teaching. Unbeknownst to her, an opportunity awaited that would allow her to bring her passion for teaching and software engineering together. 

“In 2017, I received a random InMail through LinkedIn and it was for a unique teaching opportunity. I wasn’t particularly interested but I responded only to learn that this individual lived in a building right next to mine! He offered me an opportunity that allowed me to teach high school students how to code through an organization called Kode with Klossy.” Through that opportunity, Bryan’s eyes were opened to endless possibilities as she realized she didn’t have to just teach or just be a web developer. There was a world where she could do both. 

Now, as one of Calendly’s Developer Support Specialists, Bryan helps customers with technical problems centered around integrating Calendly in their day-to-day systems. She also is able to foster her love of teaching by working part-time with Upperline Code & SEO Scholars where she has built coding curriculum and taught web development to help close the academic and opportunity gap for motivated high school students. As she reflects on her career pivots she gives advice to others looking to make a career change. “Answering that InMail helped me to find these opportunities that help enrich my life and blend both my passions in a way I didn’t think was possible.”

Fellow teacher turned Calendly team member, Ashley Macken, shares Bryan’s passion for teaching and has a unique story of her own on how she ended up at Calendly. “I knew I wanted to be a teacher so all of my education was centered around that. I ended up teaching elementary school for over a decade. In 2013, I won Teacher of the Year and was recognized as one of the top 20 teachers in the state. That really gave me visibility into exploring other areas of teaching such as administration, curriculum building and more. My teaching career ended up going into curriculum design and I started to see similarities in my skill set to jobs in the corporate setting.” 

Macken began networking and researching possible job opportunities that her skill set could easily transfer to and she ended up landing a job at E*Trade as a Training Manager in 2019. After a merger and acquisition and a pandemic that continues today, Macken was ready for a change. “I took on a new hobby during the pandemic, tennis, and my tennis partner happened to work at Calendly. We had a conversation one day when we were discussing learning and facilitating and she was like, ‘You know? You really could be a great fit for this opportunity on our Sales Enablement team at Calendly.’” And the rest is history.

Macken joined Calendly as our Sales Enablement Manager for Customer Success in 2021 and has enjoyed every minute of it. Seems easy right? But Macken assures people it does take work to change careers, it doesn’t just happen. “Teachers have a huge skill set that is untapped. I’ve found that there are so many ways for you to pivot as a teacher with the skills you develop in the classroom. Don’t let impostor syndrome prevent you from having conversations. Also, saying yes to every conversation [can be a lot of work] but, every conversation is a win because it helps you practice for those conversations that are of value.”

It is never too late to change jobs or even careers. Whether it is finding a new passion or bringing passions together, be open to that InMail or that conversation with a tennis partner. You never know when opportunity may strike.