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On Merit

When I was trying to get my start in Tech, I had zero network. Working at a bakery (and teaching myself code on days off), I'd chat up every person that walked in holding a laptop to see if I could learn something from them. After a while, I started cold emailing people I found online, offering an Amazon gift card if they'd talk to me about their experiences and give a bit of advice.

Merit is the platform I wish I would’ve had then.

Nearly a decade later, I was introduced to Merit by a friend and immediately saw how I could provide value to others while meeting like-minded folks in the process.

For ten months now, I’ve spoken with an entire spectrum of people: founders and co-founders, a Founding Engineer, a Product SVP of 15+ years and so many others in various stages of their careers:

Getting first jobs out of college or bootcamp People looking to leave their current roles Individual contributors cautiously interested in management It’s remarkable how much a short conversation can change your direction and a little encouragement often goes a long way. I’ve never forgotten all of those who helped me, and Merit has been the perfect place to continue to pay that forward.

What’s Merit?

Merit is a Tech mentorship platform that lets you book time with mentors on a range of career topics.

As a process, Merit’s pretty simple: once you’ve signed up and been approved, you can set up your profile and search for mentors to book sessions with. These sessions are typically video calls ranging from 30 minutes and up, and are scheduled on an as-needed basis. Likewise, both mentors and mentees are able to follow-up via chat to keep the conversation rolling as they see fit.

Being a mentee

Being on Merit as a mentee has helped quickly demystify paths I've considered and assisted in taking a much more measured look at what fits, career-wise.

While actionable advice is given during sessions, it's often the slight shift in perspective from mentors that I continuously marinate on and find coming up in my thoughts well past the time we've spoken.

It’s within these shifts that I find the good stuff: wisdom that can’t be spelled out or listicle’d or boiled down to soundbite, but understood only by being present in an open conversation with someone who either is or has “been there™️.”

Likewise, it’s worth it to share some of the notes I’ve taken to further emphasize the absolute gold found in these conversations; I hope they are as helpful to you as they’ve been to me.

Session excerpts

The following are excerpts from notes taken during sessions as a mentee (with express permission to publish).

Arjun Kannan, Co-Founder

“Creating opportunities to collide with good people is how you make amazing things happen.”

You were the chief of both Product and Tech - how did you straddle that?

That's an odd question for me, because I really don't see a difference between Product and Engineering. We want the exact same things and each one informs the other.

Flexing those product skills…how do you get decent at that?

Talk to your customers —a lot— observe them in their daily habits, it automatically becomes clear what they want to ask. Your engineering skills here are more applicable than you think: this is just a squishier form of debugging.

Any other thoughts regarding startups?

Don't validate your solution, validate the problem you’re solving. [The ethos of] 'Measure twice, cut once' is actually wrong in startups…it often costs more to measure than it does to cut. If you're willing to make a mistake and the price isn't too costly, you'll be more encouraged to do great things.

Pablo Napolitano, Founding Engineer

“Reluctance to scale was enticing to me, keeping venture out as much as possible.”

When interviewing an early stage startup

Learn how much leadership would pivot if necessary, ask up front in the interview, "What do you do if something isn't working, how different would you pivot on this?"

What else should I ask that I don't know to ask yet?

  • Find out whether you're joining an org that already has a product team. If they don't, know that you'll have to do product work. Learn how familiar the founding team is with the Product process.
  • Look into what regular working hours are, what that looks like for them - you don't have to kill yourself in a Founding Engineer position - iron out those expectations beforehand.
  • Ask for the Founding Engineer title.
  • If you're a Founding Engineer, you're basically an investor, so you should treat the interview process as such, from understanding your own equity exit plan (getting sold/ IPO/vesting schedules/cliffs) to looking for equity leeway as well, for example:
  • "If you raise another round, could you buy back some of my stock?”
  • "During future raises, are there times to exit for existing investors?”

Jim Lindstrom, VP of Product & Engineering

“Constrain yourself through frameworks - ex: using story maps to map out a problem, writing design briefs to crystalize my understanding of a problem”

What resources would you recommend for someone looking to learn more about Product Management?

  • Teresa Torres's Blog - Teresa is one of the best writers on product [along with Marty Cagan]. She's at the forefront of where the field is headed, but writes in very concrete, usable ways.
  • Melissa Perri and Gibson Biddle are also well-known writers on product strategy and have some good stuff.
  • What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services. - Really interesting way of using Jobs and Outcomes to drive product development. It makes a ton of sense to me in existing markets, and especially with fairly simple products that do one or two jobs. I'm on the fence about its applicability in newer markets, with more complex products, and with tons of potential surface area. One thing I really like, though, is Ulwick's approach to defining opportunities. Feels super useful for organizations that struggle with how to set product strategy that isn't just a laundry list of features (e.g. most places I've ever worked).
  • JTBD-motivated interviewing - Bob and Chris are, I think, coming at this from a marketing background, vs an eng or product one, and so I think they have some unique perspectives to share. This video has strongly affected the way I interview folks now.

Kirk Fernandes, Co-Founder

“At a meta-level, as a founder, you define your own metrics of success. So be regularly evaluating that, asking yourself, ‘why am I doing this?’”

“There's so many kinds of entrepreneurship, there's VC-backed versions, angel-backed versions, etc. You're the only person who has the answers and that itself can change as well. We ask ourselves all the time, ‘are we the specific people that need to solve this problem?’”

Insights as a mentee

As a mentee on Merit, I’ve been able to more easily understand my own path in leadership along with a solidified decision to look for a role within an earlier stage startup. The conversations I’ve had on Merit have further instilled the notion that there are so many ways to play the game, and finding the one that fits best for you is well worth the journey.

Being a mentor

Being able to assist others on their paths in Tech can be incredibly rewarding and Merit provides ample opportunity to do so. Below are some common themes I've often chatted with folks about.

How to leverage what you have and where you currently are, career-wise

I’ve noticed that newcomers to Tech sometimes try to hide the very things that make them so unique: their past experiences. Often, these resume omissions are incredible strengths (previous business owners, managers, high end retail, etc) and are worth leaning into rather than dismissing. People can downplay themselves, though you have a lot more than you think, and leveraging your past experiences can help ensure you shine in the interview process and beyond.

Figuring out where you want to be in the Tech landscape and how to get there

It can be difficult, even if you’re already in the industry, to figure out where you want to go in this massive space. There’s no real rulebook to this stuff and career ladders typically aren’t one-size-fits-all. Everyone comes to work with a predisposed set of beliefs and desires; in mentor sessions, we often try to unpack that together and find some actionable steps forward.

Weighing the pros/cons of leaving vs. staying at a role

When to stick it out? Is the grass actually greener? Your mileage may vary on this one…I often try to get folks to take a longer range view of their careers and needs, along with a non-invasive understanding of their financial situation to work together and see what could work for them. Leaving a role can be a very emotion-based decision (still valid), though often it makes sense to walk folks back a few steps to reconsider how they could reframe their situation or leverage where they’re currently at to build an environment more conducive to their success. If it’s truly time to pack your bags, we consider next steps to do so along with making sure you leave with intention and particularly, grace.

Interviewing can suck: how to build yourself up for it mentally and improve

This is probably the most common thing I speak with folks about and of course, I’ve got some opinions. There’s a commonly held belief that one must always abide by the inherent power dynamics of interviewer/interviewee, though I try to underscore the fact (particularly for Tech newcomers) that interviewing is always a two-way street and taking ownership in your part of the interview is essential: from making sure to set time for your own questions (don’t be afraid to interrupt), to asking pointed questions (“What’s the current ethnic diversity ratio in leadership?”) rather than canned ones (“How’s the culture?”) to find out if it's the best place for you.

I often try to get folks to consider that interviews, at their root, are still just conversations between people: mistakes will be made, sometimes things won’t go well, and you can’t beat yourself up over it if things don’t work out. Like other relationships, the outcomes sometimes have nothing to do with you, and rarely will you get transparency on that process to know either way. But as they are conversations, it helps to do what you can to dial any anxiety back to have a more free-flowing discussion, and I’ve got a few opinions/techniques on that too.

For each person, I try to get a rundown of what’s going on in their interviews, specifically which round they’re getting stuck in, and see where we can grow from there. I’ve seen some not getting initial screens (we then examine resume/portfolio and current strategy), others hitting snags on Data Structures/Algorithms questions or take-home tests, and sometimes it’s a behavioral round so we’ll do a replay on what they think went wrong. Interview prep can work wonders to ensure you put the right foot forward to see if it’s a mutual fit.

Finally, I've been happy to review individuals' CVs, portfolio websites, LinkedIn profiles, and of course Github profiles and associated repositories.

Insights as a mentor

As a mentor on Merit, I’ve gotten the opportunity to help others by providing career direction, building up their interviewing confidence, and showing them the strengths they already have, quite often, in spades. It’s within these sessions that I witness a changing landscape in Tech and a pragmatic optimism that I too, get to share, long after our sessions have ended.

Your turn

I’ve had a blast getting to talk shop with others on Merit for the past ten months, it’s been extremely rewarding to assist others and get a bit of feedback toward where I could grow too.

If this blog post has made you even halfway curious, I’d encourage you to sign up and book some time with folks for some questions you probably have on your mind. Even mentors have mentors (is it mentors..all the way down?) and it’s up to us to work together to actively build the environments, relationships, and workplaces that we wish to reside in.

Likewise, I’m on Merit.

P.S. THANK YOU(!) to my editors that helped push this piece forward: Sairam Sundaresan, Alisa Sano, Kirk Fernandes, and Brian Astrove.