After Spending a Lifetime Watching Loved Ones Work Jobs Well Below Their Potential, She Took Matters Into Her Own Hands; Interview with Rachel Serwetz

SuperCharger Ventures
4 min readJun 2, 2021
Photo edit by: SuperCharger Ventures

This interview is part of the EdTech Female Founder (#EFF) story series brought to you by SuperCharger Ventures.

What inspired you to start your EdTech Founder journey?

CEO and Founder Rachel Serwetz, an ICF-certified coach, has experienced firsthand the lack of effective support for career exploration and job search at several points of her professional journey. On her own, she learned everything about how to land a great job, leading her to secure a role at Goldman Sachs. Over the next few years, she was referred to hundreds of professionals who similarly needed career support, she saw patterns in the issues they faced, and she came up with a unique career exploration process.

After spending a lifetime watching loved ones work jobs well below their potential, and after six years of searching for her own career clarity, Rachel crystallized that her passion was helping others find theirs. Rachel knows what it feels like to love your job and also to hate your job, and worse, to feel in between. She believes that everyone deserves effective guidance to make thoughtful career choices at every step along their path.

Now, WOKEN scalably supports clients to find their ideal job direction in just a few months

Describe your company in one sentence.

WOKEN is a career exploration and job search platform including both live career coaching and a web-based platform to guide professionals through a step-by-step process of learning and reflection to clarify their ideal career path and efficiently land a role they will love.

What has been the most difficult moment as a founder and how did you overcome it?

Bootstrapping in general is tough — it requires more patience, scrappiness, and resilience than usual. Early startup pitch competitions were hard for several reasons (partially worthwhile because we earned some money, and it forced us to maintain momentum and prove traction, but was difficult feeling a constant sense of subjective judgment). Also, the first time I had to fire someone was very rough. However, it taught me the importance of implementing and discussing role expectations and culture fit; it’s never too early to talk about those topics, and it’s often missed and underrated in the very early startup days yet it is immensely impactful on outcomes. I honestly needed to talk to my therapist to get through this one!

What can the EdTech industry do to improve the gender gap?

This feels like a really big problem to solve in just a questionnaire :) If you mean the gender pay gap, versus women serving in and being promoted into leadership roles, I think a few critical steps include a) salary transparency b) objective performance assessments c) inclusivity training.

Can you tell us about a role model of yours?

Jeff Taylor, Ray Dalio, Adam Grant, Steve Jobs, RBG, my parents

Can you share an example of when you had to pivot?

We were developing our first custom-coded software and I realized our designer wasn’t experienced enough in SaaS Product design. Another founder helped me zoom out to realize this and I had to stop investing our resources into the development of that product (we had a long roadmap ready to continue developing, but without a solid design foundation of the tool, pausing made the most sense). I had to make the call to pause and figure out a new team and approach moving forward. We ended up redesigning and redeveloping the entire thing, in an 8 month journey (plus the time it took to find and hire the new team). It’s hard to pause, pivot, re-hire, and rebuild something completely, but it would have been worse to continue investing in a product that wouldn’t serve a strong foundation for the future.

What will you consider as success in 5 years from now?

Having a full-time team of ~100, helping thousands of clients per month, influencing clients’ improved career outcomes including increased career clarity, efficient job searching, and more informed career pathing, improving the capabilities, power and value of our software, implement our software in various relevant B2B settings to help ensure professionals have career support early and systematically, and to be ready to start to think about brick and mortar spaces.

Anything else You’d like to share?

We leveraged tools in a very scrappy way to create our MVP. In essence, clients paid for agoogle sheets MVP that looked and felt like a web platform. So, don’t be afraid to start small and scrappily to prove your concept and test demand.

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