Thrown into the Fire: Growing Up at a Startup
Reflections on my last six years at Bluecore, a high-growth startup in New York City.
I remember waking up at 7 AM one morning roughly six years ago and checking my phone. It was just like any other morning, except this time there was a message with “URGENT” in the title and a long string of replies already. My inbox automatically opened the last reply and it was something to the effect of “Don’t freak out when you read this — it will all be okay.”
I had just started working at my first tech job at a small startup three months prior. The message was from my manager, and there was a serious production issue caused by a code change I had merged the evening before. An issue that got all three co-founders out of bed at 1 AM in the morning.
I had recently attended a coding “bootcamp” in New York called The Flatiron School to learn the basics of computer programming in order to make the career transition into tech. I was hired on to Bluecore — then TriggerMail — as the second Forward Deployed Engineer (FDE), which is what we call our client implementation team.
From Day 1, I can remember being thrown into the fire, learning everything there was to know about our customers, our technology, and our industry. I was writing production code with a pretty loose code review process, and talking directly to customers multiple times a day. The weeks were long with lots of weekend homework. The team was about 20 people at the time, with ambitious plans to grow as quickly as we could.
The production-incident I caused was pretty embarrassing for me, but what was remarkable was how it was handled. All three co-founders met with me throughout that day and told me it was okay. “Mistakes happen, make sure to learn from them” was the theme. I was still pretty embarrassed for a long time after that, but I was so grateful for my colleagues who supported me and didn’t treat me differently after. We just kept moving.
Fast forward a few months, our FDE team starts growing and (only a few months in myself) I started training new teammates. I started teaching them the ins and outs of our system and walking through how to engage with customers. I became a team lead one year into the job and then a manager two and a half years in. Having never done either of those roles before, I was quickly forced to learn from first principles and really just see what worked and what didn’t. I watched other managers/coworkers to see what was working for them.
Three years in, I decided to make the switch into Product and join the team as a product manager. We launched our first ever self-serve UI the year before, so I was eager to see how I could apply my in-the-weeds knowledge of customers and implementation to solve our problems. Again, this was a role I had never done before.
(Honestly, I had no idea what a Product Manager even was when I started at Bluecore.)
Suddenly, I was collaborating with engineers and expected to write proposals for new features that would solve our business challenges. One of my first tasks was being asked to scope out a potential new second product line for on-site capabilities. (I barely knew how to PM projects for our primary product line at the time!)
Fast forward another three years and now I’m on the product leadership team, owning many of our customer-facing workflows and UX, and the company is over 250 people.
Many of my friends are on their 2nd, 3rd, or 4th jobs now in technology since I joined Bluecore back in 2014, and I often get the question on why I’m still here. It can be hard to succinctly articulate the journey I’ve had, but here’s my best try at a shortlist of key takeaways:
- People Are Everything
When I caused the production incident three months in, I could have been yelled at, publicly embarrassed, or fired. I wasn’t. This was one of the first times in my life that I realized it’s important to work with good people, not for when things go well, but for when things go wrong. You need good people who will learn beside you (regardless of job title, experience, or age) and help you navigate obstacles as they come.
When a company grows rapidly over time like we have, it’s not going to be easy. Things are going to change fast — from technology to competition to team structure — and you need to work with people who take the changes in stride (we use the word “grit” a lot here) and support each other every step of the way.
Fortunately, at Bluecore, I’ve had a chance to work with some of the smartest people I know, and the default is always to show kindness, generosity, and respect. I’ve met many people who I believe will be lifelong friends. I go on regular coffee dates with ex-coworkers who’ve moved on. The folks I’m closest to are the ones I’ve faced the hardest challenges with and came out the other side. The ones who have grown beside me.
Like many tech startups, Bluecore prides itself on having a good culture and hiring good people, and I believe for the most part we’ve done it.
2. Startups Change Every Six Months
I often try to tell people I interview to not join a startup unless you welcome change and growth. Over the past three years, we’ve hired hundreds of new people, reorganized a few times, opened overseas offices, and added new product lines. With this type of rapid change comes huge opportunities for personal and career growth.
While I transitioned departments internally halfway through my tenure, I’m certainly not the only person who’s done so. Other FDEs have joined Sales, Engineering, and Product. Customer Success Managers have moved to Sales roles. And lots of folks have become managers for the first time.
Startups are a breeding ground for opportunity because everything must keep changing to keep up with the new demands of scale, and it’s almost always a matter of choosing what you want next versus lack of opportunity. For folks earlier in their careers just starting out and even for more tenured folks who want to explore new things, this is huge.
3. There Will Be Rough Patches — Guaranteed
While it’s easy to reminisce about the great times, it’s also important to remember when things got rough. Times we had to work around the clock to deal with technical issues, times we worked really really hard — on the wrong product bet, times when friends quit or got fired. With tons of learning opportunities also comes tons of mistakes. Times you don’t really know how things are going to work out. Often, these are the times that people start leaving to pursue other opportunities.
There’s a sentiment in tech that people should be constantly looking for a bigger, better opportunity, especially if they hit a rough patch or don’t like an aspect of their job. And in tech, there are always better opportunities out there.
But, at the end of the day, I think it’s the journey — the struggle — that matters most.
The good times are so much better when they are hard-earned. Sometimes knowing the 100 ways something won’t work is just as useful as knowing the one way it will. It’s hard to regret the abundance of learnings I have from the challenging times I’ve seen and the mistakes I’ve made along the way (even if I don’t always want to think about them).
When I step back from my day-to-day, I try to remember that 99% of people have not built a company from scratch. 99% of people have not navigated these same problems. So to be one of the 1% who actually gets to see a seedling startup grow into a real company and deal with all the challenges of scaling fast is actually quite a remarkable honor.
4. Great Achievements Require Time
It’s funny how stories change given time. When Bluecore started, we had no self-service campaign workflow UI. To build quickly, we focused on only essential self-serve components, which at the time was deemed to be reporting and analytics.
Two years in, we hit scaling challenges and finally invested in a fully self-service product. It took us most of a year to build and migrate customers to it. And it was hard — we worked late into the evenings, dealt with many bugs and issues, and six months later, it barely seemed to move the needle on self-serve adoption. Sure, it made internal flows easier, but customers weren’t really using it.
Looking at those same metrics now, four and a half years later, the hard work of that team in 2016 is one of the main reasons we have over 90% self-serve adoption on our flagship product, Bluecore Communicate™. The hard work of that team is one of the reasons we are now able to onboard, retain, and grow hundreds of the top retailers in the world.
Many of the engineers, designers, and customer success folks that were here during that rough patch of 2016 left never really understanding how successful that initiative would turn out to be — because it took years for it to truly show results. We also had to restructure our Sales, Customer Success, and Support operations since then to adapt to our changing product. It was really, really hard at points. But looking back, it was the foundation of all our future success.
If it’s not clear so far from this post, I grew up at Bluecore. It’s comprised 75% of my working life so far. I did a lot of things for the very first time. I’ve learned so much in so many ways. I’ve made a ton of mistakes. Could I have learned the same amount at other companies during the same amount of time? Quite possibly.
But looking back at 24-year-old me, I would say I was really lucky to find this ragtag group of folks daring enough to take on established industry-leaders to start a fledgling email marketing company.
I knew there was a good chance we would go bankrupt after I started, since almost all small early startups do. I remember the thing that struck me most when I interviewed here originally was that the people seemed ridiculously smart and like good people to learn with for a year or two even if the company didn’t work out. Luckily, it did and they were.
And the journey isn’t over yet. As we head into the new year, we still have aggressive plans to hire another 100 people and maintain high YoY growth (all while still navigating a once-in-a-century pandemic). I’m confident the problems the team will be facing this coming year are unlike any we’ve seen before the last six years I’ve been here. The team will get bigger, the problems will get harder, the technology will keep changing, and our customers will have new needs. I’m sure in a year, I’ll be a new person, working at a new Bluecore. In many ways, being in that continuous journey is the most exciting part of all.
