Interview: My Career Journey

Since graduating from University in 2003 as a teacher, my career has taken many interesting and unexpected turns. Though this blog focuses mostly on life coaching, the majority of my professional life is spent at tech company Automattic as a senior manager (“Lead of Leads”) in customer support with

I was recently interviewed as part of an internal series on career development, and it was fun to reflect back on what brought me here. My current role is truly a synthesis of so many different experiences and is where I get to put most of my coaching skills into practice.

If you’re a multi-passionate person, your career journey is far from linear, or you’re simply curious how someone goes from high school teacher, to Thai massage therapist, to tech company manager, then this one’s for you.

The Path to Automattic

How did you find your way to where you are today? Share a little about your professional journey.

As a yoga teacher and wellness coach, I created a WordPress website for my business, and was a regular blogger. A friend of mine started working for Automattic as an engineer, and told me about the Happiness Engineer position. At the time, after 8 years of the ups and downs of solopreneurship, I was seeking the stability of employment and the role sounded like a perfect fit!

The team lead position intrigued me right away as I enjoy leadership, mentoring, and coaching, so I started on the leadership path here fairly quickly. Within my first year, I led what was then the G-Suite guild, completed the leadership cultivation program, and became a Happiness team lead with About a year into that journey, I completed a six month rotation with HappEx as the first lead of the Happiness Onboarding program (now HappOn), and when I came back into, I stepped into a Lead of Leads position, which is where I am now. 

How (or why) did you approach each step in your career? Is there a perspective that helped you transition into each new role? 

For the most part, each step in my career journey felt like a natural transition, following whatever inspired me at the time. Sometimes circumstances forced my hand more quickly, such as being laid off from a position as a program coordinator at a nonprofit in 2008 during the economic crash. Since being at Automattic, I follow my curiosity and step up to the plate whenever I feel I have something valuable to offer. This includes teaching several wellness workshops since being here, both on Zoom and in person at the Grand Meetup. I greatly appreciate the openness and receptivity this company has to ideas and allowing people to explore and express their passion. 

What do you wish you would have known when starting out in your career?

That your career path doesn’t have to be a straight line with one clear goal. Instead, you can allow the journey to unfold. I think what’s most important is being as fully present as possible, and doing your best work. Keep identifying areas where you can serve, and the rest unfolds quite beautifully. If an opportunity doesn’t work out, another one will present itself at the right time. 

Also, the best thing you can do when you’re looking for a new job or a career change is talk to everyone you possibly can about it. The more people who are aware the better. It helps you expand your network and opens up possibilities you may not otherwise have considered. 

Which tools or resources would you suggest to someone interested in the same career as yours (books, professional groups, work process, mentoring, courses…)?

Working with a coach during times of transition, or when you’re ready to grow, is always valuable and something I believe anyone can benefit from. A couple books that helped me identify my strengths and therefore determine where best to place my energy: 

Now, Discover Your Strengths, Marcus Buckingham and Donald O. Clifton

The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level, Gay Hendricks

Is there anyone who has inspired or supported your journey?

Many people have, especially the mentors and coaches I’ve worked with, from my yoga teachers, to my coaches, and my leads here at Automattic. I think mentorship is a key element to meaningful growth and advancement. 

Navigating Automattic 

What is your current role at Automattic? How would  you describe what you do to someone who is unfamiliar with this work?

I’m a Lead of Leads in Happiness, which is essentially a Senior Manager in Customer Support. My primary role is to mentor team leads with performance management, nurture their growth as leads, and to ensure high quality support in our division. 

Before working at Automattic, what was the most unusual or interesting job  you ever had? 

One of my favorite previous jobs was as a Thai massage therapist. I trained in California and Thailand, and had a small private practice in my home in Los Angeles. I really enjoyed those sessions with clients. It’s wonderful to do work where the entire aim is to help someone relax and feel great. There’s a lot of stress in this world, and it’s a privilege to help relieve some of it. 

What is your favorite part about working at Automattic?

Working with incredibly kind, intelligent, and talented people all over the world. My 1:1s with my team of leads are consistently uplifting and inspiring. 

What drew you to Automattic originally? And how has Automattic changed since?

What drew me to Automattic was my experience with WordPress, my passion for high quality customer service, and the flexibility of working from anywhere. All of those original aspects are still present, and since being here I’ve grown tremendously both personally and professionally. 

How has Automattic helped you in your career development?

The leadership opportunities I’ve had here have helped me increase my confidence as well as my ability to collaborate. Probably the biggest benefit of all is that I am much more likely to ask for help than when I first started at Automattic, and I believe that’s actually one of the key reasons that I’ve had several exciting roles since I started. I’m not afraid to put up my hand to lead projects even if I don’t know exactly the best way to approach them. I trust that the resources are out there, and I ask a lot of questions. This helps me connect with people and build valuable relationships. Collaboration also tends to ensure success in a way that working alone doesn’t. 

Which part of your job or working at Automattic are you most passionate about? 

Coaching my group of leads. I love helping people think strategically and find their own creative solutions. It’s also wonderful to nurture confidence and growth, and help my leads do the same for their team members. 

How would you describe Automattic’s approach to career development to someone interested in working here?

When you do good work and show initiative, opportunities for growth and development abound. As long as you’re curious and you’re looking for ways that you can contribute positively to the company, the pathways are there. 

Where to next? 

How do you continue to grow and develop within your role? 

I now get to collaborate with different colleagues than when I was a team lead, which means new opportunities for learning and growth. I will start working with a coach again before the end of the year, which I believe is one of the most valuable benefits that Automattic offers. I also seek out opportunities for learning as often as possible, such as attending conferences, People Labs, talks, and signing up for workshops. 

Do you know where you’d like to see your role or skills progress in the next 2-3 years? If so, how do you plan to pursue your growth? 

Coaching is a passion of mine, and I completed a Life Coach certification program last year. I recently delivered a talk at a leadership conference on Cultivating Independence Through Coaching. I know that whatever I do, I want coaching to be a large aspect of the role and will continue to pursue opportunities that allow me to serve in that way. 

3 responses to “Interview: My Career Journey”

  1. Your journey is very inspiring, Sasha! Being open to possibilities should be the most important aspect of anyone’s career.

    1. Hi Mushrit so nice to see you here! Thanks for reading my post. I’m glad you found it inspiring.

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