While most of my advice is geared toward teachers, I’ve started to get a steady trickle of requests from transitioning administrators. I’m hearing things like…
- Are there are any EdTech roles particularly well suited for former principals?
- How do I transition from district leadership to EdTech?
- What should a school leader’s resumé look like?
Since I taught for a grand total of two years and don’t know what it’s like to be an administrator, I interviewed two of my incredible colleagues to broaden my perspective. First, Rita Wright shares her journey from Deputy Superintendent to National Academic Advisor, and then Ross Jeske shares how he transitioned from an Assistant Principal to a Sales Development Representative!
If you’re a transitioning teacher, keep reading anyway — Rita & Ross have tons of valuable insight about finding your passion, handling rejection, and putting your best foot forward during any job search.
Rita Wright: From Deputy Superintendent to National Academic Advisor
Rita Wright spent 13 years as a classroom teacher and 15 more as an administrator, guiding curriculum, instruction, and educational technology in both large and small districts. A long-time user of Renaissance solutions, she joined the company nine years ago and now directs a team of National Academic Advisors.
Why did you become a district administrator, and why did you ultimately decide to transition into EdTech?
Leaving the classroom is not easy for anyone who is called to make a difference! For me, becoming an administrator was about maximizing my sphere of influence. I knew I was helping the kids in my classroom, but I could help even more kids by helping teachers. In addition, my colleagues frequently encouraged me to pursue leadership positions.
When I did become an admin, I missed the classroom but loved shaping the bigger picture and feeling like I had an impact on curriculum decisions. I’m also a data geek — I enjoyed diving into the numbers as both a teacher and an administrator!
I worked for the same district for 20 years and left when I knew my job there was done. But when I left education altogether, I had been in that district for just 7 months! It was a last minute decision with multiple factors. I knew I loved being second in command at a district, but I didn’t want to move into a superintendent’s seat; as a superintendent, you can lose touch with the education side and become a policy maker who deals mostly with school boards. Even so, I knew I wasn’t done with my career and I wanted a new challenge. Renaissance had been recruiting me for several years so I finally gave it a shot. The stars aligned!
What do you do as a National Academic Advisor? Who is well-suited for that role?
I tell people, “I’m an expert from out of town.” I come with education knowledge and product knowledge since I was a user and customer for many years. I speak the district’s language, so I can translate between the salesperson and the educators and hear the “questions behind the questions.”
When I talk to administrators, they like that I’ve been in their shoes. Perhaps a district wants to use our assessment tools but isn’t sure how to set the right benchmarks for student mastery. I can have that conversation with them before the sale to help them feel confident in the tool they’re about to purchase.
My role exists at other companies, but might be called something else, like “Consultant” or “Solution Expert.” On the other hand, you might see a “Consultant” job that is really about Professional Development/Training or Project Management. In those roles, you take a customer from purchase through implementation — it’s another good place for educators to land!
What qualities make someone successful as a consultant or academic advisor?
You have to be quick on your feet, and able to respond quickly. That comes from depth of knowledge and confidence in your products, but it also comes from actually listening to what customers say and responding to that. Those are hard skills to teach but they’re very critical.
You need presentation skills, too. Administrators might not have created their own slide decks in five years. You can’t get away with that in this job. You have to go back to your roots and start from scratch; you don’t have a secretary anymore!
When you’re interviewing candidates for the National Academic Advisor Position at Renaissance, what positive and negative things stand out to you?
Change is good, but it’s a red flag for me when people have hopped around to different schools and districts every year. Some stability is important to see. Obviously there are exceptions, like if you served in the military or had a spouse in the military.
The more relevant your experience is, the more likely it is that you’ll get to the next round. When applying for a role like National Academic Advisor that requires at least a decade of education experience, you likely need more than a one-page resumé to give sufficient detail. If you’ve had a multi-decade career, go back as far as you need to to show that you have deep expertise; show me that you started as a teacher and how long you taught, and prove to me that you have the necessary background knowledge to do the job.
If you make the effort to pull out the things that match the job description, that makes a big difference. Your experience is absolutely transferable, but if a Sales-focused person is hiring you, they can’t read between those lines on the resumé. Say that you “implemented 5 new programs to get buy-in from teachers” instead of that you “bought new textbooks each year” — you’re not lying, but you’re framing your skills so that someone outside of education can understand their relevance.
Do you have other advice for administrators seeking something new?
I remember when the Regional Manager was reaching out to me, they offered me a Sales position first. I said, “But I’ve never sold in my life!” She responded like this: “Rita you sell every day. I’ve seen you sell a new policy, I’ve seen you sell textbooks, I’ve seen you sell new curricular solutions.” Carrying that further, teachers are selling the value of education to their students. So don’t sell yourself short!
In addition, you can’t just jump because you’re unhappy where you are. You have to follow your passion and look at where you’re actually going to be happy. Anyone with the heart and mind of an educator has to really believe in the company they work for — otherwise, you won’t feel great about where you land.
Ross Jeske: From Assistant Principal to Sales Development Representative
Ross Jeske worked as a teacher, Dean of Students, and Assistant Principal before transitioning into Sales earlier this year.
What was most challenging about your transition from school leadership to Sales?
It was hard to overcome that initial fear of rejection and the inevitable canned replies you get, like…”we appreciate your interest and while your professional experiences are impressive, we have decided to go in a different direction.”
For those that stepped into their very own classroom straight out of college and then made their way up the ranks within the same school district, that rejection can be crippling. You can easily start believing that you’ve pigeon-holed yourself and your skills won’t transfer to something new.
Dealing with rejection is so hard! What tips or strategies helped you get in the door with companies who might have otherwise overlooked your skills?
Resilience and a really strong introductory email/cover letter! I used the cover letter as my chance to control the narrative. Instead of letting hiring managers see my experiences as potential weaknesses, I pulled essential functions of the role from the job advertisement and showed how they aligned with those of an educator. In Sales, for example, I’d obtained a ton of experience listening to my students’ pain points and finding different pathways to address those concerns on the fly; this would be crucial in the role of an SDR on the phone with a frustrated teacher.
I also stayed on top of job board updates, felt comfortable casting a wide net, and made sure to be prompt and courteous with any correspondence I sent. While the first Renaissance position I applied for didn’t work out, I believe my conversation with that talent acquisition leader helped me get the SDR job 6 months later. You never know what notes will be entered about their experience with you and how that may open up another opportunity down the road, so strive to be understanding, courteous, and responsive even if you don’t hit the home run on your first try.
What initially drew you to Sales?
I grew up with three brothers and had an innate love of competitive sports through high school and into college. I have always strived to be the best in whatever role I was in. In the world of education, this resulted in high-scoring evaluations as a teacher and accolades as an administrator, but I always felt like something was missing. I could find intrinsic motivators to continue to work hard, but I knew there were others around me making the same pay as I was (if not more because of years of experience) and doing half the job.
In Sales, my work ethic and performance could speak for itself and would be rewarded with higher compensation. This would ultimately put me in a better financial situation to support my family.
Did you ever worry about feeling over-qualified for your new Sales position or have concerns about starting over given all the leadership you had attained in a school setting?
A resounding yes to this question. There were almost always two little voices sitting on each of my shoulders as I evaluated job openings. One saying, “you are above that role” and another saying, “you can pave a new path and once you get your foot in the door, and you will rise to the top just as you’ve done before.”
I think listening to both voices was important for me. It allowed me to rule out some positions if the salary would not have been what I needed; I was determined to find a role that would be competitive with what I was already making, but had a way higher ceiling for advancement than what was ahead of me as a Principal. Sales offered exactly that!
Any advice for school admins who want to try something new?
Embrace the philosophy of “Expect nothing & accept everything.” This helped me overcome the initial rejections and learn to trust that the right position and right group of people/hiring manager would see my past experiences and skills as strengths that I could bring to a new role. These are the people you want to work for anyway!