So you want to be the CTO of a tech startup; get ready to roll up your sleeves.
In June of 2017, I accepted the position of CTO at Remine, a technology startup headquartered in the DC area building real estate software to help provide real estate agents with nationwide access to data that combined public record, consumer, MLS listings, and other data sources in a geospatial product with robust search experiences, data visualizations, and predictive analytics.
Prior to joining, I had worked at several companies including Sandia National Labs, Palantir Technologies, and CEB holding various roles from Software Engineer to Product Management director to Director of Engineering. The opportunity felt like the next step in my career and what I had worked hard towards all my life. I felt like this was just the next chapter and that I was totally prepared. Or so I realized how much I would learn.
I’ve been asked by a lot of my friends and peers to explain what my experiences have been, and after almost two years I feel like there’s so much more but was good time to just stop and reflect.
Jumping into the deep end
When a startup is already in full motion, you are jumping head first straight into the deep end of a company. Although there is a short period of time when you’re in the honeymoon phase of your new job, there’s work to be done and people who are looking at you to help take the company to the next level.
At the time I joined, there were only a handful of employees at the company who worked diligently to build the first version of our product and proven its need in the industry as demand increased and adoption increased. I realized one thing really quickly about this new job: time to roll up the sleeves and get to work. FAST.
The first chapter of my job was about building. Building a scalable platform and a team that would take us to where we needed to be. We didn’t have a technical recruiter to start — it was about taking the network of people you trusted that you once called your friend, co-worker, boss, or direct report and convincing them to come along with you on the journey.
This part of the startup process you won’t read or hear a lot about. When you read blog posts or articles about the challenges in startup you find a lot of common themes quickly:
- Hyper growth and scaling
- Raising funding
- Defining startup culture
Your first hires as a CTO are critical. To this day, those that decided to join me in the journey at Remine are still here and are as passionate about what we started to where we are now.
You always have a plan. But sometimes you have to call an audible on the playbook.
Each and every day at a startup early on is truly different and an adventure. For those who need very structured days or definitive long-term plans, this can be a challenge. This isn’t to say the leadership teams don’t have a plan. To get to where you want to go, you have a lot of obstacles that you must first learn, thrive, sometimes fail and get back up to find your way.
Startups define their culture on how they identify and solve problems. For some, it’s about resonating their best practices and processes around companies who have done it to scale and in many minds, successfully. Some choose to be pioneers, creating unheard of practices and cultures that deem them brave and innovative but increase the risk of potential disasters or fail. Either way, how you and the rest of the executive team shape your company will set a tone for how your company operates, the type of culture you hire and attract, and the day to day on your employees’ jobs.
In the beginning, I thought everything could be planned, predicted, and navigated in a structured way. I learned that you do all the planning in the world to only come to a juncture where you have to improvise, think strategically, and call an audible on your play you’ve chosen.
There is no job or task beneath you. Get your hands dirty.
I’ve always respected my peers and leaders at my previous companies who made me feel like they were in it with you at their jobs. Even when a company becomes large, you hear about how motivating it is to employees when their executives take the time to talk, learn their names, and just be “normal”.
It’s important that as a leader of the company, you represent what it means to work at where you are. At Remine, you’ll often see the executive team doing a lot of manual work around the office whether making coffee for the staff, cleaning the floors after a spill, wiping down areas when they are dirty, or even washing the dishes.
There is no job or task beneath you. People want to be around others who lean in, support, and help each other. At the end of the day, when you say it’s about teamwork, that includes yourself even if you’re the CTO. Roll those sleeves up and get your hands dirty.
Code. Ship. Repeat.
When starting off in the beginning when there were only single digit numbers of folks that reported to me, it was easy to just feel like “one of the engineers”. Late nights, lots of coffee, problem solving, white boarding, coding, debugging, you name it. The traditional tech startup routine. As one of my favorite shirts from Palantir had on the front, “Code. Ship. Repeat.”
But then our company grows. First to 15, then a few months later to 60. Six months into my role, Remine had grown to over 60 employees. Our rapid expansion in growth in team size and all of the accomplishments of our teams had taken us to the next step of startup life, growth and scaling time. By now we just launched our products live into general availability in the first few markets.
Our Engineering and Product teams were working diligently around the clock to push new features and capabilities and fast as we could. One of our fundamental and core beliefs was that our users and customers deserve the best and most that could be provided from a technology and user experience perspective.
The success and reviews of our product continued to drive further demand as more and more features were requested and markets continued to go live with what we’ve poured our sweat to build. As we kept working harder, it seemed that there was way more to do each time. This repeat cycle was no joke and as leaders at Remine, we knew our momentum had to continue to drive change in the industry for a much needed technology gap.
Set crazy goals and crush them
To get to the stretch goal of having Remine provide access to one million agents in a little over a year, we knew that we would have to do something in the industry that hadn’t before. We had to build products, workflows, and features that would enable our end users to have access to data and capabilities that weren’t as centralized and accessible in one application. It has not been done before in the real estate technology scene at the speed, scale, and agility.
From the onset when I learned about what the founders of our company wanted to deliver, I thought it was all just crazy dreaming and goals. As we set our goals one by one, our teams with the unheard of deadlines and goals that we internally chose began to meet each one consecutively and consistently.
Our teams continued to grow and soon after we stopped to reflect on what had just happened compared to a year previous, what was once said “not doable” or “too hard” was all done and we were on to the next goal. Our ability to design, build, and deliver quality software continued to move forward and next thing you know we were increasing our difficulty in the next task exponentially.
It’s always crazy when you first start. But if you surround yourself with the talent who can think outside the box with diverse technological and product backgrounds, your scrappiness and willingness to hit those crazy milestones will take you further along than you initially thought.
It’s not about you. It’s about everyone else.
You see it everywhere. The leadership quotes, books, and sayings about leading from the front rather than the back. If anything you read or hear, this is one I’ve never disagreed with.
Being a manager, leader, or executive — it’s not about you. It’s about everyone else.
You have a responsibility to shape how your company does, what your employees work day and experiences are, and how you ultimately run your teams and products.
The title of CTO to me is just a title. For the leaders who forget what it means and what it took when you were an individual contributor, you will lose the people who elect to follow you and work on your team.
Your success is on your team’s success. If you could do it alone, you wouldn’t have hired help.
I have a lot of 1:1s with my staff and folks around the company who want to know what it’s like day-to-day in my role, or my career path on becoming one. Remembering that I was in their seat thinking one day I wanted to be a CTO myself, I always seem to share with them how much I stay up at night and work on weekends thinking about what I can do better and how do I continue to keep my teams motivated.
Your job becomes a responsibility as a CTO. To your company, your customers, and most of all, your employees.
Maintain focus and keep the bar high for everything.
Fast forward to May of 2019. A few months ago, we successfully raised our Series A funding of $30M. My team has over 90 people. We have multiple products in several verticals with an international rollout right around the corner. Remine as a company announced last year of its MLS 2.0 product, one that will truly revolutionize the real estate vertical by providing the real estate associations and realtors with a modern technology platform that will allow for the creation of house listings, syndication with a unified experience that will allow for consumers to work better in a frictionless process.
As we grow — our focus hasn’t been more stronger. Our path and where we want to be is right in front of us. While we are hiring and continuing to augment our teams, our bar continues to be high if not higher. It is important that you never settle, continue to ask questions internally, and most of all — have a high self-awareness of how you can be better as the CTO.
At Remine, we are still pressing forward. Lessons are still being learned. Our culture still being defined as we learn more about ourselves and who we are becoming.
I haven’t hit my two year mark as CTO yet (just under 45 days from now) and there’s so much to go, grow, learn, and stride towards.
Bottom line: there isn’t one path to being a CTO, it’s about making one yourself and figuring out how to come out on the other side.
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