Being at an early-stage startup is a bit like being in grade school — but in this version, you have to skip a grade every 6 months and still get all As. You learn quickly because you have to. And while you manage to skip grade after grade, there are many times when you fall short. Then, once you’ve graduated, you look back and realize just how much you’ve learned, and how much you wish you could help others have an easier time with their path.
That’s exactly why I joined NextView Ventures team a little over a month ago — to share my knowledge and experiences with companies skipping grade after grade to better our everyday lives. And I learned a lot helping Blue Apron grow 25X in 3.5 years.
While my memories are still fresh, I wanted to share them with other founders, early teams, and aspiring entrepreneurs. Here are a few things I wish I knew back when I started my journey at Blue Apron.
Individual teams need a well-articulated mission and vision, too.
Most companies know it’s important to clearly define a mission and vision — that’s how you bring people along and keep them motivated. However, I learned that a functional team could also benefit tremendously from articulating its mission and vision.
When I first took over Blue Apron’s small product management team in early 2015, I realized that it did not have a well-defined identity and purpose. That’s not a unique experience for PMs — the definition of “product management” is bound to be different at every single company due to the GM-like, cross-disciplinary nature of its work. But product management was even more confusing at a company such as Blue Apron because it offers both a physical product and a digital experience.
The lack of clarity definitely had an impact on our team morale, communication and collaboration friction with other teams, and recruiting.
So I went onto a “soul-searching” exercise. I looked inward to identify how Blue Apron as a business could really benefit from its product management team. I also sought perspectives from product leaders at other companies to understand what their teams stood for and why.
What we landed on wasn’t really anything revolutionary, but putting our values on a piece of paper — and referring to it at decision-making moments — helped bring a renewed clarity and focus to the team. Plus, it helped us communicate our value to the rest of the organization, making collaboration way easier.
As the leader of your team, the work doesn’t stop at setting a vision. Without garnering support and alignment with internal leaders and constantly educating the rest of the company of your team’s purpose, you will not set your team up for success.
Leaders need to proactively and holistically manage their org design.
As a company goes through hyper-growth, it’s easy to fall into the trap of letting teams grow like weeds in the backyard without conscious decision on the landscaping. After all, who has time to slow down and review org design when you needed these people yesterday (or better yet, yesteryear)?
In reality, there are real costs and hidden inefficiencies when teams deal with growth pressure by making hiring decisions in silos. Not only can siloed hiring result in overlapping skillsets, but it sometimes drives conflicting team objectives.
I saw this first-hand with Blue Apron’s approach to hiring for data science and analytics. I led a centralized data science and analytics team, but we also had analysts on other functional teams such as customer experience, supply chain, and operations. This design happened organically as teams tried to move quickly—it was often easier to hire some directly on your team than negotiate for resources. But as time went on, we started to see inefficiencies around resource prioritization, talent development, and quality of the work. It wasn’t an impossible situation to fix, but being thoughtful upfront would’ve set the teams up for success from the beginning.
To make sure teams stay “MECE” as the company scales, department leaders should champion for their POVs. But it’s the CEO’s responsibility to ensure team growth aligns with her vision for the company — and play tiebreaker when necessary.
Consider making “how teams are growing” a standing discussion topic with the entire leadership team every 3-6 months. (This is NOT the same as reviewing annual headcount plans.) When you establish a frequent forum for such conversation, you are more likely to identify and correct misalignments before they’re too late.
Stay ahead of the chaos and invest in “ways of working.”
Scaling fast means chaos and complexity hit the organization before it’s ready (and it never is). One of the costliest aspects of increased complexity is it makes collaboration across teams much harder, even when teams have good intentions.
Blue Apron’s corporate headcount grew from ~20 when I joined in early 2014 to ~500 in early 2017. The growing pain, and the feeling of “Wow things are different! I can’t get things done as easily anymore,” were acutely felt every time the headcount doubled. And being able to effectively collaborate across teams was especially important for Blue Apron given the hybrid online/offline nature of its product and experience. Everything we did — even the tiniest change in the product — required the teams to move in lockstep.
It eventually became clear to me that I could make the most impact by working with other leaders of the company to help redesign how our teams got work done—such as streamlining a decision-making process for cross-functional projects and defining teams’ roles by the types of initiatives (“need to be in the loop” vs. “key decision maker” vs. “decision contributor”).
I wish that we had proactively prioritized this versus playing catch-up, as these types of inefficiencies quickly and materially impact speed and morale.
If you think your company is about to enter a high-growth period, you and other company leaders should do your best to rise above the chaos and invest energy in proactively designing better team collaboration.
It is a hard discipline because this just doesn’t feel that important compared to many other more “real” priorities on your to-do list. But think about it this way: If your company was an orchestra, wouldn’t you spend most of your rehearsals synchronizing all the music instead of just making sure the violinist plays a beautiful melody?
Decide where you sit on the “speed vs. polish spectrum.”
Most people have heard of Facebook’s early mantra “Move fast and break things.” It sounded controversial (break things?!) but it helped everyone at Facebook understand how to make tough decisions and prioritize resources.
In general, speed and polish (or experience/perfection) sit on two opposite ends of the product spectrum. You can’t have your cake and eat it too — when you opt for one, you are bound to short-change the other.
Since the very early days of Blue Apron, we’ve put a lot of emphasis on polish — the thoughtfulness of the experience (both physical and digital), the attention to details, and the pursuit of user delight. We believed that a polished experience was one of the best ways to build trust with our customers, and earning the right to tell people what to eat for dinner certainly requires such trust. However, we were also a company that would not take “slow” for an answer — the question was always “How can we do this faster?”
When teams get pressure from both sides without knowing where on the spectrum they should aim to be, you get a subpar product with compromises that achieves neither. And as you scale, the problem gets worse, as fewer and fewer people understand how the company wants to approach this trade-off.
Regardless of where you’d like to be on the speed vs. polish spectrum, articulate it and make it part of your culture. There’s no doubt that early-stage startups face tremendous pressure to “move faster” — but that is precisely why defining where you sit on the speed vs. polish tradeoff is important. When you send a consistent message on your company’s framework, you position your teams to continue to move fast as you scale.
“Common sense judgment” will stop scaling.
Many startups resist establishing rules and processes because they feel “corporate,” but some of them become necessary (and even helpful) as you scale in headcount. Just like you can’t defy gravity when it comes to physics, you also can’t defy the impact of headcount growth on your organization.
When the Blue Apron product and engineering teams were relatively small, it was fairly easy for the team to stay aligned when it came to product quality. The quality bar started with what I deemed production-worthy, and I gradually instilled such standards onto the team through product reviews and QA process over the years.
But one day, I noticed a clunky experience on production. My first thought was “This must be broken!” After taking a closer look, I realized that this experience was released intentionally.
At that moment, I knew common sense judgement — specifically my judgement — had finally stopped scaling. We had to introduce some clearly defined standards to align the teams.
Standards help set clear expectations, and processes help reduce the burden of ambiguity. You will be surprised by the positive impact of introducing more well-defined standards and processes, if done the right way at the right time.
Invest in first-time people managers — you’re going to have a lot of them.
Talent is the number one bottleneck when it comes to scaling, and many fast-growing startups struggle with the “build vs. buy” talent decision (more on that in a separate post).
If you’re growing at a breakneck pace, you will inevitably have to rely on some of your high-performers to step up as people managers as you scale. Don’t take people management skills for granted — being an excellent individual contributor requires a very different skillset than being an effective people manager and leader.
I became a first-time people manager while at Blue Apron. I joined as our first product hire, and then 15 months later I became Head of Product, managing three other PMs and one designer (and needing to hire two more PMs immediately). As the company rapidly grew, I had to master the many aspects of people management and leadership as I encountered them for the first time — attracting talent, crafting a vision, scaling a function, coaching, motivating, balancing control and empowerment, and time management.
I was lucky to have a very supportive manager (Ilia Papas, our founder and CTO) who devoted bandwidth and energy to be a sounding board and thought partner along the way. Blue Apron also offered leadership training for all people managers and exec coaching for its senior leaders, both of which were tremendously helpful in helping me evolve my management and leadership style.
I would count my personal journey into people management a reasonable success, but I also know many others who were not set up to thrive. Despite the fact that they might not be your most senior leaders at the company, ineffective people managers are extremely costly to the organization. Bad people managers result in unhappy and unproductive front-line employees, directly impacting the quality and volume of your output.
The best way to scale your impact as a leader is to develop effective leaders for tomorrow.
After all, tomorrow’s the day you skip to the next grade — and you need great leaders on board to help you do it again and again and again.