Office Hours: I was formerly VP of Engineering at Discord, and, before that, Director of Engineering at LinkedIn. Now, I’m an advisor, seed investor, and a fractional exec. AMA!Featured

Posted in:Software Engineering Office Hours Management and Leadership

Hi Elphas!

I’m Prachi Gupta. I have over 20 years of experience in consumer technology companies, with a proven track record of building and managing engineering teams that deliver impactful software.

I was formerly the Head of Engineering at Discord, and, before that, Director of Engineering at LinkedIn.

At Discord I was responsible for growing the engineering team from 60 to 300, along with scaling the systems and processes to unlock business maturity and IPO readiness. As part of the executive leadership team at Discord, I had the opportunity to work with the board, and the rest of the executive team to shape its broad culture and business functions, in addition to providing technical and people leadership.

At LinkedIn, starting as a software engineer, I either built or led teams that built a broad array of consumer products, including communities, messaging, exponential growth engines, user generated content. When I left LinkedIn, I was leading the team behind LinkedIn’s homepage and content feed. My time at LinkedIn taught me everything about building distributed, highly scalable consumer products, transactional engagement models, user life cycles, as well as building resilient teams that outlive individual leaders.

Before LinkedIn, I’ve also worked on wearable devices including their software layers, and deep data systems that enable dynamic data processing and presentation.

During my downtime, I enjoy strength training, rowing, and playing video games (being a completionist, right now I am trying to wrap up the new enshrouded extension). I’ve also recently started picking up some hands-on home improvement projects, the latest being a redesign of my home office.

Ask me anything about managing engineering teams, being a fractional executive, consumer tech, prototyping ideas, being a closet gamer, having young kids, or anything else!

ElphaStaff·Aug 19

Thanks so much for joining us @Prachi!Elphas – please ask @Prachi your questions before Friday, August 23rd. @Prachi may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕

Milica·Aug 21

How do you make tech buying decisions on such a scale? For example, how do you go about adding new and open-source tooling? Is it easier to get people excited over open-source tools than hosted ones?

Prachi·Aug 23

Hi @Milica, the build vs. buy decision is essentially a multi-variable problem and the result is different with each situation. Generally speaking a big part of the decision comes down to what you want your team to focus on building themselves (usually this is whatever your business's secret sauce is) and everything else which supports your overall goal but doing it yourself is not going to generate a unique advantage for you.I am personally a fan of using open source software where it makes sense, specially if the community is large and thriving. Open source software with a large, active community is almost always evolve and improve faster than proprietary software. I also like the idea of being able to open up the code, understand it, and customize it for whatever I need vs. waiting for someone else to take in my request. But, I also make sure I have enough people on my team who are dedicated to, and responsible for maintaining and evolving any open source libraries we use, so we can control our own destiny.In terms of what's easier to get engineer's buy in on (open source vs. hosted), I think it really depends on what the team's goals and motivations are. For product teams, a tool is a tool, they want to spend their time building on top of the tools, but for the tools team, the ability to control and evolve the tooling/infrastructure is a big deal. Often times, for a startup, the decision might come down to operating costs of either solution. Similarly, for a large company, open source might be a good starting point, but almost always they need something custom to support their scale, so they will end up customizing or building stuff in-house.

ajasinger·Aug 23

Thank you so much @Prachi! It sounds like you’ve had such an interesting and impactful career so far. What’s your advice for a junior engineer to:1. Get noticed in the interview process 2. Make an impact in their first job Thank you for taking the time to do this!

Prachi·Aug 23

@ajasinger being a young engineer is such a fun and amazing time in your career, it's the time where you can focus on learning and exploring and leverage your interests to shape your career. There's a lot of different ways to stand out early on in your career because each company values something different, and every team has its own mini culture.In my experience, showing an interest in your work, being infinitely curious, showing an ability to learn new things in depth, and most importantly, really loving what you do (which shows up in things like what you do in your free time, side projects or open source work you do) helps hiring managers see you apart from the crowd. I've personally never cared about where you got your formal education, and focused more on what candidates say they are passionate about and what they've done to pursue that passion. I've hired high school students as interns, because of this passion and the fact that they had active community projects just because they were passionate about some problem.

madien·Aug 22

Hi @Prachi! Thank you for your time. Your experience is impressive, and a few nuggests caught my eye - which I would like to know more about:- You mentioned "Building resilient teams that outlive individual leaders" - what are some of the do's and don'ts to accomplish this?- You mention you are a fractional exec: what are your challenges in this work and how do you overcome them? - Also what (in your opinion) are the pros/cons to the business, of hiring a fractional exec? One common lament is that fractional workers do not have the skin in the game, therefore I would like to know your take on it. - What path would you suggest to do fractional work related to data and AI strategy and product management? TIA!!

KasiaAdvisor·Aug 21

Hi Prachi, so great to have you with us! I'd love to learn more about being a fractional executive. How many companies are you working with in that way? If more than one, do you find it hard to switch focus?What kind of compensation range can someone expect in a fractional exec role?What is the best way to find fractional roles in your opinion?I'm asking on behalf of my executive coaching clients.Many thanks!Kasia

Prachi·Aug 23

@KasiaAdvisor Just like every other business, starting off with consulting and building a network and client base that leads to "deal flow" takes time (on the order of years). There is obviously an appeal in the idea of exploring fractional roles, you get to leverage your years of experience and expertise and engage in temporary engagements with some flexibility in the pace and hours of work you put in. What I've found is that signing up for specific projects with a very clear and specific goal/success criteria works much better compared to just taking on an open ended role for a short period of time. Doing the first gives you, and your client clear expectations, as well as a relatively clear way to quantify impact. A fractional role is not the same as being an advisor, your success as a fractional executive relies on your ability to dive deep fast, find a solution and execute it flawlessly, while building trust with the employees at the company you interact with. So it's hard work, you actually end up working much harder in short bursts of time compared to medium intensity all the time at a full-time salaried position. It's kind of like high intensity interval training :).Compensation range on these engagement can vary a lot and depends on a lot of factors like length of engagement, complexity of the problem, your personal baseline of expenses as well as preferred forms of payment etc. Generally speaking, a good way to think about it is to evaluate the benefit your work will bring to the business, and decide on a reasonable % of the dollar value of that impact.

jenniferhenderson·Aug 20

Hi Prachi! Can you recommend what metrics I should be checking to understand eng team velocity/ output? We've recently hired several new eng teammates - staff, EMs, etc. and I can't get a straight answer from my team about what we should expect in terms of increased output now. TYIA! **we're series B, ~25 pp in eng for reference

Prachi·Aug 23

@jenniferhenderson thank you for asking this question. It is honestly a question I've heard from every CEO I've worked with, how do I tell if my engineers are productive enough, or am I getting enough of an ROI on my hiring. It's definitely a natural question for every CEO to wonder about, especially since talent is often the single largest expense for most knowledge businesses. I too have spent time exploring this question, talking to other heads of engineering across all size of companies, and there's good news and bad news! The bad news is that no one has found a metric that is definitive enough to answer this question. But, the good news is that there ARE some things you can look at to at least identify leading indicators which you can then use to poke further and understand discrepancies. For example, you can look at DORA metrics to gauge if you have a DevOps process that is able to release new software as well as correct defects quickly. For the development process itself, you need to get a sense of each team's position in the product lifecycle (eg. validation, experimentation, pre-product market fit, scaling etc.) to set the right level of expectation on output. For example, a feature that's in validation phase, should move quickly (release changes every day/week), vs. the one in experimentation phase, you likely need to wait a couple of weeks between feature updates to collect data etc. If your question is about the general velocity change you should expect per hire, at each level of seniority, the answer to that starts with understanding the hiring plan to start with. What was the reason to hire the people you hired, what was not getting done, that this specific role would unlock. Assume an onboarding period of 4-6 weeks for technical roles, but you should be able to see if the hires are going to have the impact you expected in your hiring plan within 4 weeks. For example, are there technical decisions that were blocked and dragging on because there was no one to make the call? Hiring a technical EM focused on that problem area, or better yet a skilled senior or staff engineer should immediately start unblocking these hung decisions, which should show up as an increase in rate of code commits for the adjacent teams etc.I am happy to talk more privately if you want to explore this question further.

jenniferhenderson·Aug 27

Immensely helpful, @Prachi! Can't thank you enough. I've heard of several of these options from my eng team and your response helps me ask better questions for future conversations. Grateful for your advice!

heidivogel·Aug 23

Hi, I am impressed by your journey and knowledge. Having build products for big tech what is your view on how AI can improve our life and our society that is extremely connected. What are your hopes AI will solve?What best idea did you had to leave behind you during your journey, because there was no budget (time, resources, momentum), and you regret not fighting for. Love to chat with you, Heidi

Iynna·Aug 21

it's wonderful to have you, Prachi! You have a super inspiring career especially as a technical leader. I am early stage investor, what type of companies do you like to look at for your investments? I'd love to share you some quality deals! And regarding hiring: a lot of the companies in my portfolio (and beyond) are young startups always looking for strong technical and engineering talent. It's obviously very hard to find great talent so I am curious, do you have tips to source and identify them? And ways to attract them - salary itself won't be anything like big tech but outside of equity and potential for growth, what are elements that resonate the most, in your experience?

Prachi·Aug 23

Thank you for your kind words!Re. investments, generally speaking I look for smart people who are passionate about the problem they are trying to solve and have a great work ethic. But I am happy to talk in more detail about specific investment over DM.Re. attracting early talent, everyone knows the importance of the first 10 hires you make at a startup. These are the people who will not only make or break the company, but also the ones who will define and set the long term culture for it. Smart people like to work with other smart people, so first and foremost, they need to see and know that the executives are whip smart and someone they can see taking the company to success long term. If there's a technical leader in place already, they absolutely need to know why they are in the position they are, are they the sharpest engineer they've encountered? Do they have the ability to inspire and lead? And the last two ingredients are if they as an individual passionate about the problem you are trying to solve and will they have the autonomy to solve it with you.Great talent can come from any place, some of the smartest engineers I've worked with were self taught with a string of side projects. So I'd definitely look at who's active in the communities surrounding the technology that's key for your business and engage with engineers there.

Liana202·Aug 21

Wow, you have an amazing profile! Did you have any particular philosophy or strategy for moving ahead to each new opportunity in your career (and life, since you have kids as well)? Thank you for sharing with Elpha!

Iynna·Aug 21

she really really does have an amazing background 😍!

cassielowell·Aug 20

Hi Prachi! Thanks for taking the time to do an AMA.I'm a startup founder in the tech space, and while we're a small team right now, we're obviously hoping to scale. I'd love to hear about your strategies for maintaining (or purposefully changing) your engineering team's culture as you grew.

KasiaAdvisor·Aug 21

Hi Cassie, that's an exciting time! I'd be happy to share with you from my experience as well if you would like?

cassielowell·Aug 22

Please! Always happy to get additional perspectives, since everyone approaches situations a little bit differently.

Iynna·Aug 21

this question is ON POINT! I'm not a founder like you, but I am an investor and this question is key!

KasiaAdvisor·Aug 21

In my experience one of the most important things is equip engineering leaders with coaching skills to ensure diversity of thought is brought out and to create a culture of innovation, engagement & belonging. As an Investor I'd pay attention to if they also invest in building capacity in their people or if they only invest in the tech

manjuladharmalingam·Aug 20

Share some tips for building profile for fractional executives along with expected remuneration from your experience.

Leana188·Aug 21

Adding a please and thanks would go a long way :D

madhuchavva·Aug 21

Hi Prachi, That's an amazing and inspiring career path you've got there! I've considerable experience in the IT industry and a tech startup that's pretty early stages. As someone with aspirations to step into the VC world, what would be the ideal path for me to begin my journey? Appreciate any guidance or suggestions you can offer!Thank you so much for taking time to answer our questions and Keep rocking!Cheers,Madhu

share this article