I Spent 17 Years in Tech: My Career Is a Dumpster Fire

ranee
12 min readOct 7, 2022

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“Dumpster fire” is an informal term to describe a catastrophically bad situation, like my career.

This post is dedicated to everyone who is silently suffering from workplace mistreatment or burnout, and may take comfort that they are not alone in feeling the way they do. And for those who may feel trapped in their position due to family and financial obligations, know that I understand how it is to be emotionally depleted, inhibiting one to make even the slightest of changes. It is my hope that everyone allows themselves some room to reflect in their values and priorities, engage in acts of self-care, big and small, and evaluate future opportunities with increased scrutiny.

I was asked about my Twitter account in an interview today, and it compelled me to share this story. Which I didn’t take offense to at all. In fact, I loved that they asked me. I appreciate it when someone genuinely takes the time to ask and learn, rather than cast judgment. Much of what I say through social media lives without context, which I am, for the most part, fine with. I don’t feel the need to expand on most of what I say since my network is mostly for marketers by marketers. Which is why, up until now, I typically assumed, IYKYK.

Why do I say the things that I do, the way that I do? It’s because not enough people are in a position to voice their opinions and call out poor decisions and bad behavior — in fear of retaliation and losing their jobs.

So I do it.

When people look at my resume and academic pedigree, they typically make the assumption I’ve had a pretty good career with impressive achievements — which I have. That’s what a resume does anyways, it shows off the best bits. My close friends though, watched me go to Hell and back. As a woman executive in tech, my career has been a rollercoaster— mostly petting zoos disguised as rocketships — where you leave the barn with either shit on your hands, Covid or worse — and manage to continue smiling. I’ve been a people manager my entire career, which has been a learning curve of its own — filled with hard lessons learned and lifelong friendships. I’ve been through my fair share of startup successes and failures — where the up was way up, and the downs spiraled into a deep dark abyss I never want to talk about or revisit again.

In truth, my social media presence is merely one lens of my entire career, hopefully my story will contextualize my experiences to better understand my point of view. My fellow women and dear marketers, I know you know ☺

My Top 10 Career Lessons & Advice I Would Give My Younger Self

When a business decision seems “funny” to you, that’s your gut screaming. It’s a red flag. Trust your gut. A “funny” business decision typically signals there’s more where that shit came from.

People make poor business decisions all the time, myself included — understanding why, though, and the context, is important in learning whether you’re on a team that makes smart or poor decisions.

I once worked at a startup that had no process to shipping products. At first, I thought it was part of their organizational growing pains. They just closed a later-stage round of funding, and typically companies at this phase of growth go through lots of operational transformation and change management. It’s chaos. Where there’s mess, apparently there’s me!

As I conducted a deeper gap-needs analysis, I learned that product development was stunted and stalled because the product vision itself was based on the whim of the CEO. This debilitated the CPO from introducing any process to product development, since it would likely be changed based on the CEO’s opinions. This manifested into further organizational problems:

  • product managers couldn’t do their jobs, leading to high churn
  • lack of alignment on product launch and go-to-market strategy
  • shifting release timelines made it difficult for marketing to create programs to support launches
  • sales/customer success had no idea how to communicate products and services to customers
  • customers don’t understand the producsts/ services/ solutions delivered
  • lack of market and customer research to support the product roadmap led to shipping products/features no one wanted, needed or cared about

If you become a cofounder of a company, make sure you know your cofounder/s well.

According to CB Insight’s 2021 survey on Why Startups Fail, “wrong team” and “disharmony between team/investors” were both top reasons why startups sputtered. I didn’t fully understand how true this was, until I experienced this first-hand, at four different startups.

The most memorable though, was a startup that built one of the leading products in its category, and were 9–12 months ahead of its direct competitor. After a huge in-office blowup between the cofounders that uncovered months of arguments, investor and lawyers were forced to step in. It took a toll on the business. While our cofounders were in a bitchfest for 3 months, we lost all momentum. Our direct competitor focused on fundraising and shipping — while we ultimately shutdown. That competitor went public last year, and has a market value of $6B today. Yes, you can say I’m still salty.

F&F does not stand for Friends & Family. It stands for Fucked & Fucked.

I once worked at a startup where they were funded by one of the cofounder’s wealthy parents — who was also on the board. Unfortunately for our startup, they were more parent than objective board member, and ended up derailing our ability to make decisions as a leadership team. This caused the startup to switch strategies every few months — the organization was in constant disarray, and people were unable to be productive in their work. The entire sales-marketing team eventually churned.

While I have a few friends who’ve made it work for their startups, however, I’m personally not a fan of F&F or party rounds for this reason. Too many chefs in the kitchen, too much room for error, and absolutely zero persons held accountable when shit hits the fan.

Don’t ask anyone to do anything you wouldn’t do yourself. When you get into a position of power and begin to lead a team, be the type of people manager you always wanted to have.

I once worked worked at a startup where the CEO forced me to walk in the rain to buy donuts for a board meeting. I mentioned I didn’t have an umbrella, and couldn’t walk to the donut shop without getting soaked. I was pulled into a meeting room, where I was yelled at so loudly, when I walked out the VP Engineering came by to ask me if I was OK. I fought back tears and nodded I was fine, but I ended up running to the bathroom to cry.

The vivid feeling of humiliation comes back to me from time to time. It was from that moment, I knew, I would never make anybody do anything I wouldn’t do myself.

Culture comes from the top. Whether a workplace culture is healthy or toxic, the CEO is responsible for setting the tone. As the old adage goes, a fish is only as nutritious as healthy is its head. Oh, I meant, a fish rots from the head down. When the fish starts to smell, don’t eat it. Throw it away.

I once worked at a startup where the CRO would yell at the CMO in executive meetings, and the CEO allowed this toxicity to continue for months. In 1:1s, my CMO would be distressed and anxious, constantly reinforcing the need for our team to appease every whim of the sales team, whether or not it was part of the agreed-upon GTM plan. Eventually, my boss resigned, I resigned, then half of marketing resigned.

At another startup, marketing reported to the President, who was known to have a fiery attitude. Everyday I witnessed them screaming at my boss and colleagues — loud enough for the entire floor to hear. Everyone was paranoid and constantly in fear. Junior team members would purposefully call out sick to avoid team meetings, where the President would openly pick on random team members. There’s a reason why this company has a 2.9 star* rating on Glassdoor — out of 291 employee reviews.

When an executive team becomes toxic and abusive with each other and the team, it’s time to find a new job.

Fair and equitable pay means paying people for the value of their experience and the work they are performing.

I once worked at a startup where I inherited a team, and I learned later on that the company had a near 30% salary disparity between the men and women who were in the same jobs doing the same work. I brought this up to HR and was given the “this is our salary band, and it will also depend on the experience they come with…”

It doesn’t matter if a person went to Harvard or worked at Google or whatever. If there are people on your team in the same type of role, doing the same amount of work, with the same level of performance expectations, they should be paid the same or within the ballpark of each other. Especially if women are being underpaid in comparison to men for their work. Not only is this wrong. This is illegal.

Lying about your work performance is wrong in general, and will cost you your job. Lying about your work performance to the wrong people can land you in jail.

I once worked at a public company, when my counterpart VP Marketing (I was VP PMM in Product) lied about their year-end funnel metrics to the Board of Directors, and eventually the entire company at a commercial sales kickoff event. I watched this person present slide after slide, screenshots of an analytics dashboard that was full of doctored numbers. When a junior marketer whispered in earshot of me, if they should address the mistake, the VPM told them to “be quiet”.

The problem with this is, it’s good old fashioned fraud. And as an executive of a public company, I had a fiduciary duty to report it. I ended up having to retain a lawyer, and work with corporate and inside counsel as they conducted their internal investigation. It was concluded the numbers didn’t reflect or impact the performance of the company’s earnings, therefore suggested I shouldn’t file a complaint with the SEC. The VPM ended up being suspended for a short period, but was eventually able to keep their job. I wondered how this was possible — even so much as to think they were all in cahoots together. I stuck around for a while, but management made it increasingly challenging to stay. After just another month, I resigned. In retrospect, I should’ve considered their actions retaliation, but I didn’t see it for what it was then. If I did what that VPM did, I would have gone to jail, no question. I was happy to be outta there.

Doing the right thing will never keep you up at night. Doing the wrong thing will haunt you forever.

There will be a point in your career where you will have to grapple with doing the right thing, at the risk of losing your job. I once worked at a startup where I lost one of my top marketers. This marketer expressed difficulties working with a sales executive, and expressed concerns to me. The executive was falsifying growth metrics, creating new processes without buy-in from product management, and intentionally cutting them out from calls while making false promises to prospective customers. They ended up making a case and brought it to HR. In return, HR gaslit them, and the company decided to protect that executive instead. The marketer resigned.

Months later, I noticed a pattern with the same troublesome executive. I was gutted when women cried — literal tears — to me in private 1:1 meetings about being perpetually berated, harassed and verbally abused. What made it more infuriating, they were all women of color — the most vulnerable in the organization.

I initially thought, “Fuck the job. You can always get a new one!” But I recognized how privileged a position I was in, and that it would’ve been easy for me. It wasn’t simple for any of them. These women, having been victims of mistreatment for years, were conditioned into feeling they couldn’t transfer their skills and experience to any other company. Imposter syndrome kicked in. They lost self-esteem in themselves to find a new job. And watching this from the sidelines, with no authority or power to change anything, while understanding fully well the company would choose to protect its executives and not employees, tormented me every day.

As a people manager, it is your job to know your team and recognize the signals of burnout — which may manifest differently in different people.

Burnout is not an individual problem, and has little to do with one’s ability to “say no” to surmounting workloads. Neither is burnout solved with more acts of self-care: ore yoga and candles, spa days and retreats, a couple extra days off, or even what I thought would be the solution — a year-long sabbatical.

There are many categories of burnout, understanding the source allows us to better identify and help our teammates solve for it:

  • Unfair treatment at work
  • Unreasonable time pressure
  • Unmanageable workload
  • Lack of role clarity, goals, guidance and direction
  • Lack of communication and support from manager

I once worked at a startup where I was pressured to fire someone in my first few weeks on the job because they weren’t performing. After my own investigation, and asking their counterparts across the organization, I tried to push back since it was clear the person was suffering from burnout. They asked for time off, which I approved. However, when they came back, I received feedback from other executives and team members they stopped attending standups, didn’t respond to emails, and engaged in combative arguments in meetings. Later on, it became clear their burnout wasn’t due to workload, but lack of motivation and frustration in the value of their work and not feeling heard.

Burnout is absolutely no excuse for mistreating teammates, which is why I ultimately made the decision to let them go. I do think about this incident from time to time. I compare it to my own experience of burnout, and understand the reasons behind them acting the way they did. I fully and clearly understand the frustration they must’ve felt, and it pains me. A part of me feels guilty, that I made the wrong decision, and I often wonder if I could have done anything differently to help them.

No job is worth jeopardizing your health. Understand the difference between a toxic job versus a tough job. Recognize whether you are having a bad day or in a bad job.

“When you are the smartest person in a room, you are in the wrong room.” I’m torn when I think about this — on one hand, we should always strive to surround ourselves with people smarter than us, and drive us to “level up”. Groupthink is powerful and can happen without us even realizing it. We may even lose a sense of who we are. On the other hand, I am a firm believer that, as a people manager, it is our responsibility to elevate and help others recognize and realize their full potential. But how exactly do we figure out it’s time to leave the room?

I once worked at a startup for a CMO who was in the role for the the first-time, which was fine. As a product marketing specialist, I understood that my role and skillset would likely complement the team’s remaining competencies in PR, corporate communications and demand generation. As time went by, it became abundantly clear they were in over their head — the lack of skills, knowledge and experience in running a full-functioning marketing team, and most importantly, driving pipeline, was taking a toll on the entire team, especially mine.

I began absorbing gaps in marketing operations, demand generation, and partner marketing and other odds and ends. At first, I was happy to help, but I never intended my initial help to be permanent. I was drowning in my own swamp of shit and needed to focus on holding together a team mentally bursting at the seams. And while I eventually was able to let go of those extra responsibilities, over-exhaustion had already kicked in. There were days I closed my laptop, rolled into bed early and endlessly cried myself to sleep. I wouldn’t shower for days and wore the same pajamas day after day. I was operating like a train that failed to switch its tracks: completely derailed; crashing and burning my mental health into oblivion.

No job is worth jeopardizing your health. It took losing myself to finally figure that out.

Most importantly, you must always advocate for yourself and others when they don’t, or can’t have, a voice.

It’s incredibly important for those who are in positions of power and have authority or privilege, use their platform and audience to shed light on patterns of bad behavior. Most executives experience what I have. When very few say anything, the patterns of toxicity perpetuate. There’s no such thing as a perfect organization or the perfect job. It’s a spectrum of dysfunction, and it’s at our sole discretion to which end to tolerate. This is bullshit And frankly, I find it bizarre that some believe I should act politely when people waste my time with complete nonsense. The next time you see my social media posts and wonder if I’m talking about you, thoroughly think through why that is. It may reveal more about you than me.

Will workplace culture get better? I hope so. I don’t foresee significant changes until Gen Z and becomes the new generation of team leaders and people managers. What I love the most about this generation is their impassioned zest to live their values. They are open-minded and accepting of people from diverse backgrounds, they are champions of social justice, they empower others to do good with a high sense of purpose, and they believe in doing what’s right. There are a lot of jokes about Gen X being the forgotten generation, but we really need to recognize and owe them for being parents to an entire generation of passionate and emotionally-intelligent young adults. You did good, kid.

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ranee

Ranee Soundara has spent the last 17+ years building growth strategy and marketing teams for VC-backed technology startups with 5x exits, including one IPO.