When it comes to saying ‘yes’ to a job — sometimes it’s better to follow your gut!

Last fall, during the early stages of a job search, while still living in India — I came across an article by a woman who was scammed by a Silicon Valley startup. It was in a Medium email blast. I read it. I may have even smirked thinking, “that would never be me!” Penny saw red flags early on and jumped in. Why?!?!

Fast forward 10 months.

There are two articles that have been swirling and circulating in my social networks these days — an older HBR article on Why so many incompetent men become leaders? and a more recent one on how VCs talk about men and women differently. At the same time, I find myself in the company of amazing women who are in the midst of career transitions, many leaving difficult bosses to start companies and forge a path forward as entrepreneurs. I can’t help but reflect and share my own journey in a system that rewards people, even when they repeatedly make poor organizational decisions. And in sharing this, I’m taking a huge risk — a woman of color, calling out peers, publicly.

In Dec 2016, I moved back from India having worked for an incredibly dynamic leader <Shaheen Mistri>, to take on a role at a small ed-tech start-up in Chicago. The startup had a lab-school attached in an attractive location with great student outcomes — a reliable and necessary R&D partner. The founder’s charisma, energy, desire to collaborate, and a chance to build something amazing sealed the deal. I was coming off of a year-long high, having built/launched firki.co, traveling to nearly a dozen states in India, meeting hundreds of teachers and school leaders, and a phenomenal global fellowship at Teach for All. The joys of building something and seeing people benefit from it is magical. I wanted another round.

So mid-December 2016, I went to our Chicago office for an orientation session and to witness final student presentations at the lab school. The onboarding/orientation was non-existent and spending time with students <always great> left me with new questions about the role of the school in the organization. 8 months later, during my final days of working here, I find myself wondering why I ignored all the early red flags.

  • The role was ill-defined and open-ended, but I’d have the opportunity to help define the future of the company
  • Products were only being developed as/when new business emerged
  • There was no strategic or business plan, revenue projections, go-to-market strategy — actually, no strategy or plan to drive any part of the company
  • Founder had recently moved to rural Michigan, along with 5-month-old twins and a toddler
  • 3% equity [which felt high, even for a relatively young startup]
  • The founder was excited to tap into my professional networks but could offer little information about his own

When your boss loves all your ideas! By January, the excitement of a new job concealed the ick-feelings, and I chalked initial frustrations to growing pains that come with any new job. I found my new boss’s energy magnetic, enjoyed our conversations and was being asked for input on everything from product design/development to business development, marketing and communications, and implementation strategy. When I encountered a topic I couldn’t fully speak to, I found myself immersed in research and in conversations with people who could offer real insight. Because my boss quickly integrated new vocabulary into his language, I believed he knew what he was asking for! A few months down the road, I realized that his asking for suggestions didn’t come from a place of collaboration or thought-partnership, it came from a place of not knowing himself!

But requests for information are ignored! By February, I started noticing a pattern. If I saw a gap and worked to fill it, it was admired, applauded and generally encouraged. Don’t know how to cost a course build? No pricing strategy or matrix? Let’s build one! I had support from our CTO on many of these projects, but the founder rarely pulled up his sleeves to get the work done. The other scarier pattern — ignored requests for information. PnL statements, market-research reports, product development plan, sales reports. Because they didn’t exist, they weren’t shared. And if you asked too often, you were ignored. Which takes us back to — when your boss is too open to your ideas!

Conferences are a great way to gauge what’s going on! March had us at SXSWEdu — 3 days of meeting entrepreneurs, thought leaders, educators! For weeks prior to the conference, I asked my boss to go through the catalog and make a plan to meet folks on our ‘hit list’. But the first day of the conference had arrived, and he had no plans <except 1 dinner>. Being fairly type-A, I set up a few meetings, circled sessions I wanted to attend and had a happy hour on the books every evening. Over the course of the 3 days, we were not together very often. When your boss comes to an event unplanned, it raises some red flags. And when he’s unimpressed by all the people around him, you should run for the hills!

But March proved to be even more exciting when at a board meeting, he shared bad revenue projections. He was showing the board numbers that were 10x what they should’ve been. By the end of the month, the board started to wake up to a few realities that I had flagged a few months prior.

  • There was no product, only great content that still needed to be ‘productized’ <website claims over 100 courses]
  • No plan to productize, or even an inkling as to the product-market fit
  • Less than ideal relationships with existing clients, with two who routinely paid late, and only one relationship had a contract laying out the scope of work
  • The founder’s twin babies got lots of screen time during work calls

Design sessions, but no one is talking. By mid-April, we had started to develop 2 prototypes. Communication, a serious org-wide challenge. Prior to the sole design session, I gathered samples of curriculum products in the market, created a report on the challenges/opportunities related to project-based learning, looked at platform offerings. The founder and content developers had looked at these samples for the very first time. The very first time. It’s safe to say if your boss hasn’t scoped out the competition, he’s not in the game!!

It took 3 full months for me to sow the idea of creating a teacher friendly product- one with rubrics, guides, implementation supports, and in a format that is manipulatable and on a platform that is not proprietary! On the eve of the ASU-GSV conference, we worked through the weekend to ensure pitch decks, product roadmap, costs, and prototypes were in order. With little support from the founder.

With prototypes and a pitch deck <first ever to be created in the company’s history>, he headed to the ASU-GSV conference in May. This was supposed to be the make-or-break event. He needed to come back with viable leads or we would start winding down operations. We heard about 30+ conversations he’d had in 3 days, his exhaustion. In a 1–1 conversation upon return, I noticed new vocabulary and a real “fuck it” attitude. Our team lacked ‘management depth’. We didn’t have a team that could scale the vision. We knew too little about the market. We = everyone except him.

Over the past 2 months, I have been unhappy, upset, outraged. I know that a woman or person of color in this situation would’ve been shown the door — a long time ago. I have seen first hand, white-male privilege, and incompetence. Two months later, the organization has finally imploded. There are no viable leads, a lethargic product roadmap, and dwindling revenue. A slew of recent activities raise ethical/moral/legal concern. A skeletal team will remain in place to see through existing contracts [should clients’ sign].

What’s next?

I don’t know exactly where I will be a month from today. In this moment, I don’t know what the future holds.

What I do know, is that despite the challenges, I learned an awful lot about what it takes to build beautiful, usable, effective curriculum products. My excel skills improved — I built a basic but functional cost calculator. I made more pitch decks in the past 3 months than I have in the last 3 years. I got a crash course on pre-sales processes <thank you IBM>. I met some smart, courageous, funny, game-changing leaders. I also got to know the two women who brought me to this organization in ways I didn’t anticipate — being welcomed into their homes, fed, driven. I know they care deeply about this work. Their vision to bring real-world learning into classrooms is simple but miraculous. But now, more than ever before, I know, that it’s important to listen to your gut.

Dreamer, Do-er, Dissent-er // All things women and girls, equity and innovation Co-Founder @futurefor_us & Moving Beyond

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store