March 1st, 2022
Alana Anderson | 11 minute read
One of my favorite parts of building base case capital is deciding how to spend my time. As a fund manager, there’s certainly a lot to do – meet new companies, trade notes with investors, work with portfolio companies, not to mention all of the back-office work. But as a former operator and engineer, I’ve quickly found myself gravitating towards something a little less traditional. In the past quarter, I've met with 114 engineers, made 86 introductions, and closed 6 candidates for portfolio companies. During these conversations, I get all sorts of questions around what it’s like to work at a startup. But time and time again, there’s one topic that comes up without fail: the mysterious role of a founding engineer.
Joining a startup as a founding engineer can be one of the most thrilling, demanding, and rewarding experiences; however, the ambiguity and mystique around it can often be daunting to engineers who are deciding what to do next – especially those coming from more structured environments at big tech companies. In this post, my goal is to demystify exactly what it means to be a founding engineer. I’ll help elucidate what you’ll be responsible for, what qualities make you an ideal candidate, and what your career progression can look like. I’ll share real-world examples and anecdotes that I’ve accumulated over the years from working with founding engineers at companies like AppDynamics, Blend, Samsara, and the 30+ companies in the base case portfolio.
To build a well-rounded definition, I asked several base case portfolio founders how they define the role of a founding engineer. The answers I got were actually quite consistent:
A founding engineer is someone who can be the foundation of an engineering team from a technical and cultural standpoint. They set the bar for engineers who join who after them. They also have to be comfortable with the lack of structure and wearing multiple hats (e.g. frontend, backend, devops, talking to customers, etc.). Hence, often the best fit are those who want to become founders themselves. – Shin Kim (Eraser)
A founding engineer sets the foundations for the engineering organization. This translates into core architecture choices, processes, and setting the cultural values for the org. It also means setting the bar in terms of execution pace and quality, and driving how we interview. – Gabriel Spencer-Harper (Meticulous)
An ideal founding engineer is opinionated, independent, and appreciates ownership, accountability, and high-velocity environments. A founding engineer will have the opportunity to help build and lead a team around themselves and make high-level technical/architectural decisions on a complex hybrid product. – Nico Ferreyra (Default)
As Shin, Gabriel, and Nico all allude to, a founding engineer lays both the technical and cultural foundations for a company. Although it can vary from company to company, they are often the first 1-3 engineers hired within the first 0-12 months of the company’s existence. Now let’s get a bit more specific on what a founding engineer’s responsibilities actually look like.
You’ll need to write code – a lot of code. At the end of the day, your most important responsibility is to get your company’s product to market and maximize the number of product experiments that can be run. You’ll make key architectural decisions that will be pillars of the engineering organization for years to come. At the same time, you’ll have to make serious trade-offs to balance speed of execution with quality. You’ll decide what technical debt is worth taking on, what components should be built versus bought, and when it’s worth spending an extra week to engineer a solid foundation. As a founding engineer, you’ll also be the de-facto devops engineer. You may be responsible for setting up project management processes, troubleshooting performance and reliability issues, and instrumenting the CI/CD pipeline.
As a founding engineer, you’ll also have a significant amount of ownership over the product direction. You should expect to spend time talking to customers, teasing out use cases, and making prioritization decisions regarding both the short- and long-term roadmap. In many cases, you will be building features in the absence of any formal product requirement document. In fact, Stripe famously had engineers manage the product themselves for the first several years of its existence. Until you bring on a product designer, you may even end up screwing around in a Figma file every once in a while.
You should also expect to spend a fair amount of time in the trenches supporting customers. You’ll probably find yourself engaging with customers in shared Slack channels, Discord servers, or Twitter threads to answer product questions, triage bugs, or gather feedback. You’ll also get quite used to the friendly sound of PagerDuty alerting you when the product is down. In addition to putting out fires, you’ll also be responsible for setting up the observability stack and defining the processes around support and on-call rotations.
You’ll also be exposed to the people operations side of things – both when it comes to recruiting as well as defining the culture of the company. As a founding engineer, you will spend a ton of time sourcing, interviewing, and closing early team members. You’ll also set the tone for the company’s culture – from small decisions like “what should we order for lunch” or “what sorts of team bonding activities should we hold” to the large ones like “how do we run our interview process” or “how do we approach decision making”. As a founding engineer, you’ll be responsible for answering these questions on a daily basis – both directly and indirectly by virtue of your actions and attitude.
Finally, you’ll gain exposure to all other aspects of the business – from fundraising, to sales, and beyond. Although you probably won’t be closing deals or making pitch decks, you will certainly be expected to sell your product and pitch the company’s vision. As a founding engineer, your job is to support the founders in doing whatever it takes to get your product to market. A good founding engineer will “always be closing” – whether that’s reaching out to former colleagues, classmates, or friends to get your foot in the door of potential customers or investors.
For many, this is the most exciting part of being a founding engineer – getting exposure to things beyond your immediate skill set. There's so much that you will learn through osmosis by just being in the room where it happens.
Clearly, this role requires a special breed of human. A founding engineer must be incredibly technically competent, yet also versatile enough to excel in these different realms. While founding engineers can come from a variety of backgrounds, there are a few critical traits you’ll need to be successful.
We all know a computer science degree won’t teach you a fraction of what you need to be a strong software engineer – the majority of learning happens on the job. For that reason, an ideal founding engineer should have at least 2-4 years (in many cases, more like 5-10 years) of experience working as a software engineer. Of course, this might manifest itself in different ways – maybe you’ve been coding side projects since middle school or interning at tech companies since your junior year of high school. Regardless of where or when you’ve gained work experience, you should be confident in your ability to tackle ambiguous problems, build large-scale systems, reason about performance and reliability, and crank out quality code.
A good founding engineer craves ownership. Maybe you find yourself volunteering to run the company hackathon, own the new hire onboarding program, or perhaps just gravitate towardsmeatier engineering projects. If you often find yourself raising your hand to own things end-to-end, you will likely really enjoy the ownership afforded to you as a founding engineer.
As a founding engineer, you’ll also need to be comfortable operating with a lot of ambiguity. You won’t get product requirement documents or designs for everything you’re expected to build. You won’t be told which library to use or even what language to write in. A stellar founding engineer will know when to ask for clarity and when to make educated assumptions. If you tend to gravitate towards more loosely scoped projects, that’s a good indicator that you’ll do well in this type of role.
As Shin from Eraser stated in his definition, a founding engineer should be comfortable wearing multiple hats. You should expect a good amount of context switching from day-to-day or even hour-to-hour. A typical day might include anything from several hours of coding, to a few customer conversations, to a technical brainstorm or architecture discussion, to an interview or two. Depending on the business, your responsibilities might deviate even farther from those of an engineer. At Scale AI, for example, early engineers sometimes spent all day training taskers. If you enjoy this type of versatility, you’ll never have a boring day as a founding engineer.
Finally, you gotta move fast. As any startup founder will tell you, there is constantly more to do than can possibly be done. A great founding engineer should welcome this challenge and thrive under the pressure of intense deadlines. If you’re motivated by seeing your code in production the day it's written, you’ll love this job.
While you may not immediately identify with all five of these qualities, I always encourage engineers to start paying more attention to how they feel in their current role. If you’re unsure what you want to do next, ask yourself whether you might be seeking more in any of these areas. If you think you want to be a founding engineer, try to identify opportunities to hone these skills to make yourself an ideal candidate.
Given the expansive scope of this role, it’s not surprising that founding engineers can go on to follow a number of different career paths.
Many founding engineers go on to start their own companies. While nothing can quite prepare you for starting a company, joining a startup as a founding engineer might be the closest you can get. In addition to first-hand experience building an initial product, recruiting the early team, and hustling to find the first customers, you’ll also have direct mentorship from the founders themselves. The best founding engineers are also sharp in identifying areas their founders excel and where they fall short and can draw on these learnings when they go on to build their own startup. The list of startup founders who sharpened their teeth as founding engineers goes on and on. Within the base case portfolio alone, BaseTen’s co-founders Tuhin Srivastava and Amir Haghighat were previously founding engineers at Gumroad and Supergrain’s Thomas Chen was a founding engineer at Vurb. Other notable examples include Amjad Masad from Replit (founding engineer at Codeacademy), Sahil Lavingia from Gumroad (founding engineer at Pinterest), and Greg Brockman from Open AI (founding engineer at Stripe).
It’s common for high-performing founding engineers to get promoted into engineering leadership roles, especially in fast-growing startups. Engineers who gravitate more towards technology problems can take the path to CTO, whereas those more excited about people management can grow into VPE. One example from base case’s portfolio is Bigeye’s founding engineer AJ Ribeiro, who is now the director of engineering.
As a startup scales, it’s critical to find someone who is laser-focused on scaling the technology and solving the most challenging problems. This is another common path for founding engineers – to leverage their broad knowledge about how the company’s technology works and function as high performing individual contributors, such as chief architect or staff engineer. This is often the ideal path for engineers who love writing code, operating autonomously, and thinking about the hardest technical problems all day every day. Mitchell Hashimoto, for example, transitioned to an individual contributor role at HashiCorp after serving as CEO for ~4 years and CTO for ~5 years.
It’s also quite common for founding engineers to transition horizontally to a more customer-facing role. Given their proximity to the product and experience working with customers, founding engineers are often a top contender for the first product management hire. Leigh Marie Braswell, for example, became the first product manager at Scale AI after joining the company as one of the first engineers. While in the founding engineer role, she found herself taking on more and more product responsibilities and realizing that those were what gave her most fulfillment.
Although less common, founding engineers may also go on to become great venture capitalists or angel investors. Founding engineers often develop great networks – whether from their company’s “mafia”, trying out new products day-to-day, or working with customers who are also startups – that can lead to high quality deal flow. Further, founding engineers can provide a lot of value to their investments by helping founders navigate building their initial product or recruiting engineers. After transitioning to product at Scale, Leigh Marie went on to start angel investing in startups and eventually join Founders Fund.
The founding engineer role can equip you with the skills and experience you need to accelerate your career in a variety of ways – whether you have your heart set on one in particular or have no idea where you want to land.
Joining a startup as a founding engineer is an experience unlike any other – whether you’re looking to sharpen your skills before founding your own company, take on more responsibilities outside of engineering, or simply join a rocket ship from the launch pad. I hope this post shed some light on what the role entails and helped you reason about whether it’s something you’re interested in pursuing. If so, I host monthly dinners in SF & NYC for engineers to connect with founders who are hiring their founding engineers and would love to have you.
If after reading this post, you have more questions about the role or topics you'd like me to address, I’d love to hear from you. In future posts, I plan to dive deeper into your questions, discuss cash compensation and equity, and spotlight a few founding engineers to share their journey to the role and beyond.
Thanks to Ankur Goyal, Tuhin Srivastava, Leigh Marie Braswell, Helen Hastings, and Nikhila Ravi for their feedback on this post