How I Went From Teaching to Customer Success After Six Years in Education

I made the jump. 🤸‍♀️

Quit my job after 6 years in education. Knew it was time for a change.

Changing careers comes with a lot of emotions. It can be scary and exhilarating all at the same time.

You don't want to be like me. At first, I applied to lots of different jobs randomly without having a plan. Can you guess what happened?

Yupppppp. Lots of applications and lots of ghosting. 😂

Without a plan, I quickly became overwhelmed. I was trying to do everything all at once, which was stalling my progress.

Eventually through trial and error, I learned what works and landed a job as a Customer Success Coach.

All while starting from zero. With no LinkedIn connections and SaaS experience.

If you’re where I was at eight months ago, this article is for you.

Because without a plan and strategy, it’ll be TOUGH to navigate the transition.

Here’s how to do it right.

🔥Gain clarity on your strengths and what you want. It’ll save you a ton of time.

Do a brain dump.

Find a quiet place and set a timer for five minutes.

List all the things you loved about your previous career.

Write whatever comes to mind. This will help you think about the things you loved to do and what skills you acquired.

From this list, identify your strengths. Think about what you’re good at and what you enjoy doing.

Then, make a list of your non-negotiables. For example:

• I need x salary.
• I need x benefits.
• I need more flexibility.

When this is clear, you can start thinking about new careers.

Thinking back to my previous experience in education, I knew I enjoyed building relationships and guiding others toward success. I also learned how to creatively communicate concepts in a concise way.

These are some of the skills I identified that I use in Customer Success today.

🔥Research new careers and target 1-2 roles.

Start learning about different careers. The best way to do this is to absorb lots of information.

• Read books.
• Use the internet.
• Attend webinars.
• Listen to podcasts.
• Ask people questions who have experience in the industry.

Find a job that will utilize your strengths.

There is A LOT of free information around. Go find it.

My suggestion is to target 1-2 roles. You can’t go deep in your research if you’re targeting more.

After you've decided on a few potential roles, do a deep dive. Take the time to learn everything you can about the job.

After I chose Customer Success, these resources helped me:

• Gain Grown and Retain Office Hours.
• Reading Customer Success Books like Onboarding Matters by Donna Weber.
• Following Customer Success professionals on Linkedin.
• Attending Client Success & SuccessHacker’s webinars.

Having an extensive understanding of the role will help you crush the interview. But to increase your chances of getting the interview you need to...

🔥Tell a story highlighting your strengths and passions. People love stories.

Your LinkedIn profile should act as your resume.

People view it when you network with them and engage with their posts.

Make it POP. Make it YOU.

My LinkedIn tagline for example describes the qualities about me I want people to know (dynamic, relentless, creative, and curious).

My cover photo reinforces my tagline by highlighting the same three qualities.

My LinkedIn intro

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It pops because it’s bold and concise.

A lot of people connect with me because of my Linkedin profile. They’re curious and want to know more. People have commented on my cover photo, tagline, and also my about section, which brings me to my next point:

Write an engaging about section.

Use this section to tell your story and pique people’s interests.

The first few lines of my LinkedIn summary act as the “hook”, driving people to click to “see more”.

But don’t stop there!

They should be compelled to read every line.

By the end of your about section, they should understand your story but want to know more. Use this part of your profile to pique people’s interests.

If you’re doing it right, they’ll want to connect with you on a zoom call.

Posting content will also help you stand out. I posted about things I was learning, previous experiences I had, connections I made, and podcasts I was on. This all helped get eyes on my profile and showed I was eager to learn and hungry to make the transition.

People wanted to help me because I was doing the work. A lot of networking connections started from curiosity about my profile and vice versa.

People wanted to hear my story, which led to several new relationships.

🔥Build purposeful connections. You can learn a lot from these conversations.

Networking on LinkedIn played a very important role in my job search. Early on, I had an epiphany. In all of my previous jobs, I had connections within the organization before applying and interviewing.

I knew nobody in the SaaS world so I knew I needed to get ACTIVE on LinkedIn and build connections.

I engaged with others content daily and hopped on 30+ zoom calls with people in SaaS and Customer Success. This helped me meet lots of different people. The conversations I had helped me deeply understand the industry.

Prior to these conversations, I was reading books, attending webinars, listening to podcasts, and reading articles. All of this learning helped facilitate these networking conversations.

I prepared for each meeting and asked a ton of purposeful questions. On these zoom calls, I started making connections to my previous role as a special education teacher. This helped me tell my story and highlight my skills in interviews.

These conversations were the GAME CHANGER. 🙌

I gained confidence and was able to tell a compelling story in my interview. This helped me land my role in Customer Success without any business experience.

🔥Be bold. Be different. Be yourself. It leads to opportunity.

All my hard work and persistence paid off when the Director of Customer Success at Dooly posted on LinkedIn about the Sales to Customer Success handover. I was still learning about the importance of this handover and commented on her post.

I moved the conversation to a direct message and asked her a question referencing her post. From there, I purposely used audio and video messages to communicate so she could get a sense of my personality and curiosity.

Eventually, she mentioned the Customer Success Coach job opening at Dooly, which I didn’t know about prior to the conversation. I asked her if she could tell me more about the role in a zoom conversation. She gave me her calendar and that happened to be the start of my interview process.

Networking helped me book my interview, but I earned that job through my willingness to be different and my hunger to learn.

There are no shortcuts here. It takes time and effort to be prepared when your break comes.

I did not follow the “standard” way to get a job in SaaS and this led to my first SaaS opportunity.