Guild Careers: Lisa Richardson

Meet Lisa Richardson!

As part of National Career Development Month, we are highlighting some employees at Guild who have transitioned into different roles during their time with us. Check out their Q&As to see what they have to say about their career paths at Guild. Interested in joining our team? Visit

Current role

  • Manager, Communications & Strategic Initiatives

Other roles held at Guild

  • Student Success Advisor
  • Internal Communications Manager 

Tell us about your career journey and what led you to Guild.

Prior to joining Guild, I spent 10 years working in public education as a teacher and the last six of those as a Middle School Principal.

When I decided that I wanted to transition out of my role as a school leader, I stayed in my current role for a year and spent time reflecting on my strengths and personal values.

I learned about Guild through research on companies in the Denver area who were working toward inspiring missions. I attended an event featuring different speakers discussing the “Future of Education” and was pretty skeptical as I first learned about the work that Guild was doing. I asked some pretty direct questions, did my research, and was hooked on learning more about Guild. I had found where I wanted to work, but was still uncertain about the path to get there.

I have always been a firm believer in understanding the day-to-day experience of working in a company as a key driver for impacting change as a leader. I also have a deep love and passion for supporting students. When I saw the Student Success Advisor role, I was confident that it would be a great opportunity to focus on learning more about a new company and industry while also energizing myself by doing work that I felt deeply passionate about.

I was fortunate that news about the opportunity to work at Guild and my acceptance into my graduate degree program came within the same hour, allowing me to join the Guild team and pursue my plan.

What was the path like to transition into a different role at Guild?

In the same way that I spent a lot of time planning my transition to Guild, I spent a lot of time in my first few months at Guild observing and learning about different parts of the company, from attending demo sessions, company meetings, lunches and breakfasts with leaders, and more.

Attending these events allowed me to be thoughtful about identifying what interested me and where I could also add value. I began asking questions that helped me meet new people and identify what might be a good fit — but maybe more importantly, I began to identify what would not be a good fit.

When the position for Internal Communications opened up, I saw a lot of skills in the description that aligned with my past experiences and opportunities that would allow me to use my strengths. I felt confident that it would be an opportunity to grow.

Throughout the process, I was able to be open and transparent with my manager. They were encouraging of this exploration while also allowing me to navigate the journey in my own time.

How has your past work experience helped you in your new role?

As a school principal, there are many skills that you are required to master. What people may not consider about the role of a school leader is the number of business skills and leadership experience that comes along with the job — from being a direct people manager and a developer of leaders to communicating across multiple stakeholders (student, families, staff, cross-functional leaders, school boards, etc.), to being an operations expert and trainer, to hiring and recruiting talent and managing their performance, to creating, forecasting and managing a budget. I saw these skills and  experiences reflected in many roles and opportunities; however, it was important to identify which parts of my previous job were the most energizing to me in order to narrow my focus.

Specifically, within the role of internal communications, I was drawn to the idea that I would be able to leverage one of my favorite parts of school leadership — bringing people together through a compelling narrative and a strategic vision.

What are some lessons you learned along the way?

Just as important as being clear on what roles you may be able to do — it’s okay to be clear on what roles aren’t the right fit. Even if you have the skills and experience, it’s okay to not pursue a path if it’s something you aren’t passionate about. This isn’t always easy to recognize in the moment.

Consider every meeting and interaction as an opportunity for professional development and growth.

Every transition comes with a learning curve. Starting a new role can be just as challenging as navigating your career transition.

  • Be comfortable asking questions and asking for help.
  • Take the time to get to know people and understand their perspective and needs in connection to the work you are doing.
  • Be prepared to face some of the same challenges – a new role doesn’t always make things easier.
  • If there isn’t a clear roadmap for what to do in the role, begin to make one. Use the information you have gathered and your past experiences to make suggestions and decisions. Don’t forget that you are in the role for a reason.

What advice would you have for others who want to transition into another role?

  • Be really good at the role you are in. Even if it’s not what you want to do forever, it’s important to demonstrate your capacity. Consider how what you are learning in your current role may connect to other parts of the business. This perspective is important.
  • Look around you: Who do you want to learn from? What do they do?
  • Seek external support – a coach can be very helpful as a neutral voice in helping you identify your values, skills, and strengths. Our friends, family, and managers can be great – but it’s also hard for them to be totally neutral. An additional outlet to process and to help you define your goals is invaluable.
  • Growth is not always linear.
Written by Guild Education
Leave a comment 2 Comments

Leave a Reply

Your email address will not be published. Required fields are marked *