On 2 years at Maven
This past Saturday I celebrated my two-year anniversary at Maven (that’s four years in startup time). I’m trying to become a better writer so I figured this was a good opportunity to try to put some reflections on paper.
When I first joined Maven, I was focused on proving that I could execute. Coming from a completely different industry with an operating cadence on the other end of the spectrum, an early-stage startup with a team size of <25 was a big culture shock. The “drinking out of a fire hose” metaphor is a startup cliché for a reason – my first three months, every time I’d hear the Slack notification sound I would sprint from wherever I was in the room back to my laptop.1
There were so many little things I had to learn just to catch up to the same baseline as everyone else. My first two weeks I learned I didn’t actually know how to write. Sure, I had a B.A. and a minor in writing but when it came to writing a strong email, I was functionally illiterate.
On my second day, someone asked me a question and then left me unmonitored with a large spreadsheet to find the answer – I’d never been more thankful for a basic grasp of the =INDEX(MATCH()) command.2 I didn’t know what any of the terms being thrown around in meetings meant – I had the Zoom pulled up in one window and an overworked Google search bar in the other (“What is GMV? Top of funnel? What is a ‘marketplace business model’? How to spell ‘Andreessen’?”).3
Year 1 was about answering the question: “Can I do it?” Given an amorphous problem that changed every three months and a vague notion of success, could I move the pieces in the correct way to arrive at the desired outcome? (Caveat: Rachel was telling me how to move the pieces.)
My first year, I:
Scaled operations for the Maven Course Accelerator, from a starting point of ~400 students to 1300+ in our largest cohort.
Helped build the self-serve onboarding process and set up the inbound funnel after we launched our marketplace product.
Built our first outbound sales motion and launched our first AI collection (XX courses, [redacted] in GMV).
My second year has been a gradual transition to ownership. Where I spent my first year proving that I could solve the problem given to me, in this last year I’ve been more focused on: picking the problem, having an opinion on what the good solution looks like, and then solving the problem more independently while letting everyone else know how it’s going (look Ma, no hands!).
My favorite thing about the culture of working at an early-stage startup is this opportunity for growth through ownership.
I wouldn’t say that I have a natural bias for action – in fact, in real life, I’m a bit of an overthinker and a recovering perfectionist. I love to theorize and am usually not interested in doing things until I’ve planned enough to know it’ll be excellent (I can admit this now because I’ve already been hired, joke’s on you guys). But being on a small team has been a forcing function to just “ship it” – it’s equal parts empowering and terrifying to know that something simply won’t get done unless you do it. I’m lucky to be in an environment early in my career where I can practice overcoming analysis paralysis.
Part of my growth has to do with the range that my role encompasses at Maven. I’ve never worked anywhere else, but I suspect that at a bigger company, I’d be pigeonholed into doing 1 or 2 things every day over and over. At Maven, I get to do (😮) so many more things:
Some background for my friends who don’t know what I do
I look at data and cobble together dashboards to form an opinion on what the next collection should be.
Then I go do some user research to hear from students firsthand on what they’re looking for.
I’ll spend some time reading and researching the vertical, breaking down a role that I know nothing about (what IS product management, really) into a collection of 15-20 timely and relevant topics.
I’ll figure out who the “cool kids” in the space are, what signals and brand names people care about, and find 100-200 representative instructors that we think could teach (and sell) those topics.
Then I’ll craft 100-200 notes to send them.
When they respond, I’ll get on a sales call with them to convince them that this is the opportunity they should invest the next two months of their life into.
And once they’re on board, I’ll project-manage the group of instructors until they become a shiny new (hopefully) million-dollar collection on our homepage.
Plus a few other things here and there. All in all, that’s a lot of cool muscles I get to flex!
There’s something to be said about how fast you can learn just by getting more reps in. Two years in I’ve written a lot of cold emails. Every Slack I post requires so many micro-decisions: What context is important to know? What are the key takeaways and who needs to be informed? I’ve looked at thousands of instructors and tried to guess who the winners will be (am still only okay at this). I have lots of opinions now on whether certain messaging will resonate with the target audience, and some opinions on whether a design will convey the brand identity that we’re going for.
I’ve learned about the power dynamics of of selling, the precision of language required for a strong cold email, the Tetris of project-managing the 8 different plates that will become a coherent collection. If I have a question, I now know how to build a Metabase dashboard to answer it (or I ask Rishin very nicely if he’ll do it for me, please). I’m more tapped in to tech Twitter than I care to admit – yes, Dad, I did hear Chamath’s latest podcast.
Now that I’m fully immersed in the Kool-Aid the startup culture feels second nature. But when I zoom out, I remember that just a short two years ago, the longest document I’d written was an impassioned email to a angry parent, most of my days were spent wrangling 12 yr olds, and the most high-tech tool in my classroom was Google Drive. We’re not in Kansas anymore, Toto!
It’s been a good two years at Maven. I’m excited for the next one.
Some of my favorite lessons thus far
Answer your own questions, trust your own judgement.
As part of this push towards more ownership, Mickey has taken a real Mr. Miyagi-spin to his management style lately, answering all my questions with: “Well, what do YOU think we should do?” It’s very annoying.4
But it’s a great symbol for one of my biggest learnings of the last two years.
When I joined Maven, I assumed that everyone knew more/better than me. I didn’t ask questions in meetings because I was sure that everyone else knew the answer and I was just catching up – imagine my rage when Shreyans (our CTO) asked a question I SWEAR I’d been thinking but had deemed too obvious to voice and everyone marveled at what a good question it was.
I also deferred to other people to have the “right” answer, often feeling like I needed to gut-check my decisions before I could comfortably move forward. It took me a beat to adjust to the ownership of “you’re smart, you can figure it out, we hired you because we trust you to make decisions on your own” (this is a close relative of “ask for forgiveness, not permission”). I couldn’t believe anyone was trusting me with anything with all of my two weeks of experience in tech.
Two years in, I’ve gained a) the confidence to trust my judgement more and b) the critical thinking/writing skills to be able to explain my POVs. A reframe in my thinking here has been: instead of assuming that someone else will know better than I will, why not formulate my own opinion, defend it if asked, and adjust if I’m off?
I’m working on being okay with getting things super wrong. I’m cool owning the blame when things don’t go how I want them to, I know now that failure is not reflective of my worth as an employee. But I’m trying to take more shots on goal this year, trust my instincts more and come with more solutions, ideas, and opinions, not just questions.
Maybe experience is overrated – it’s could just be critical thinking + context + a little confidence in a trench coat.
What’s the why?
I pretty distinctly remember that I built a Metabase dashboard once early on in my time at Maven – lots of tables, I felt really cool – and Mickey asked how I was going to use it. I was stumped.
“You said you wanted a dashboard to track how x instructors were progressing through the funnel.”
“Right, but this is a dashboard that YOU’RE going to use. Are these charts actually helpful for you? Is this giving you the information that you need?”
A huge lesson I learned in startup world and a big departure from my time in education was that there’s no point in doing things just for the sake of doing things. As a teacher, there were lots of rituals I had to participate in for the optics of my classroom/the admin/the school, but at an early-stage startup, there is literally nothing I do just for the sake of doing it.
Anytime I start something now, I ask myself why I’m doing it. I pull the threads of: What’s the higher-level goal that this action is in service of? Is this the best way to achieve that? How much time or energy should I spend on this?
Effort is a valuable resource and I think really good operators know exactly how they’re allocating their resources. Parsing out the “why” has been great for my prioritization skills and my clarity of thought in general.
What does the other person need to know?
It’s actually not intuitive to communicate effectively at an early stage startup. Lots of people default to just word vomiting as it’s the lowest-lift way to share your thoughts.5 This does not work at Maven.
Sharing your ideas, opinions, and outcomes for easy digestion + maximum impact is a crucial muscle to develop if you’re going to succeed in a remote-first environment. Here’s an example that I wrote just last week:
Bad:
Better:
I won’t put a “best” screenshot here – I’m no Lani. But in the last two years, I’ve come up with quite the checklist to make sure I’m at least getting closer. Is the outcome/top-line literally the top line of the message? Are you surfacing the right context with the right level of detail? Are the outcomes clear and skimmable?
A side note: I was lucky enough to work with Wes for a year and now I have a little Wes voice in the back of my head whenever I write (when she reads this, she will point out that em dashes don’t have spaces on either side). They say that every gift has a hidden cost and the price I paid here is the development of a new pet peeve: I can’t stand inefficient communication in my personal life anymore. Makes me super annoying to have in the bachelorette groupchat, I’m probably never beating the “Claire is a bot” allegations.
And one thing I already knew but am grateful for…
Feedback is a gift but it’s built on trust. If you’d asked the vice principal of the school I worked at, she’d tell you that I was terrible with feedback and the most difficult first-year teacher she ever worked with (another thing I can disclose with impunity now). I think Mickey would tell you that I’m pretty good with feedback though. Why the stark difference?
At Maven, we’ve built a culture of mutual respect and trust that we’re all acting in each other’s/the company’s best interests. If Rachel tells me my copy is bad, I know she’s doing it because she thinks I have the capacity to do better – as we all know, she would never waste her time on a lost cause. When Audrey gives me advice on managing my relationship with Gagan, I know it’s because she wants me to show up in the best way. Every time Mickey points out something I could have done better, I see that he took time out of his day to help me perform at a higher-level, to notice some detail of what I did and write me an explanation for what I could change. I am so grateful for this.
I love to tell my friends that I like and respect every single person I work with just to see the surprise on their faces – it’s a very rare thing, especially this early in a career. I am very lucky to have that at Maven and it’s a testament to this thing that we all built together.
Thank you to my friends for proofreading this essay (can I call it that?). My coworkers don’t believe you exist, but someone had to workshop this thing.
I developed a Pavlovian reflex here where the little “click” would trigger a cold sweat. To this day I have the audio notifications muted.
Shoutout to the future investment bankers I hung out with in college.
I had to Google this again while writing this essay – I had it wrong in my first draft.
Mickey, if you read this, I say a lot of nice things about you that cancel this one out. It’s PEMDAS.
Pop culture has recently coined a term for this phenomenon: “yapping”.