Office Hours: I'm Heidi Williams, Director of Engineering at Grammarly. I lead B2B and platform engineering. AMA!Featured

HeidiW·Nov 14, 2021

Hi Elpha!

I’m Heidi Williams, Director of Engineering for Grammarly Business and Grammarly for Developers at Grammarly. (hiring on elpha!)

Over the past year and a half, we grew our team from zero to twenty+ engineers as we built Grammarly Business from the ground up. We also bootstrapped a team to launch and build a new product, Grammarly for Developers, our first platform offering!

I’m also the founder of WEST Diversity and Inclusion, which connects women in tech with industry leaders through cross-company mentorship.

I started my career in tech at Macromedia as a Software Engineer, spending six years there before moving into an Engineering Manager role at Adobe, where I spent over 10 years. I was the VP of Platform Engineering at Box and CTO & Co-founder at tEQuitable before joining Grammarly in 2020.

Ask me anything about leading and scaling technical teams, building 1.0 products, mentorship for leaders in tech, making workplaces more inclusive, or anything else!

ElphaStaff·Nov 14, 2021

Thanks so much for joining us @heidiwilliams26!Elphas – please ask @heidiwilliams26 your questions before Friday, November 19th. @heidiwilliams26 may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕

Slyvia76·Nov 19, 2021

Hi Heidi, thank you for your AMA.I got promoted to senior SWE then an engineering manager role pretty quickly (4+ year, luck + hardwork) in a 1000-person B2B company, mostly doing monolith product development. After 2 years, I then took a career break to pursue a master's degree in Data Science in EU. Now, when preparing for my interviews as engineering manager, I realize that I didn't know a lot about scaling a system to serve millions of users. I'm a "Object-Oriented Software Engineer that have good Data Science skills, and a DS that has good SWE skills" -- but not the top one in any domain. Although I passed many behavioural interviews easily (yet the technical...), I wonder if I should interview for an engineer role instead, as I won't be able to give solid technical advice to my engineering team and helping them to grow. Will lacking the hands-on experience of scaling the system become more severe as I grew into a more senior leadership role? Currently, I'm happier to deal with people, process, business than the technical details.Any advice? Many thanks!Slyvia

HeidiW·Nov 19, 2021

Hi @Slyvia76, your situation definitely resonates! When I left Adobe to go to Box, I had only ever worked on desktop software and all of a sudden was at a SaaS company with no hands-on experience building systems at scale. However, I did have experience building platforms and working on partnerships and had engineering management experience, so they took a chance on me that I could bring the expertise I did have and learn what I didn't yet know. My technical coaching for the team ended up being more like recognizing patterns of risk or edge cases and asking questions to help them think about the proposed solution more completely. I didn't need to know the answers, I just had to ask the right questions! So you might look for roles (and companies) where you can leverage your experience even though there are other things you'll need to learn. You have computer science and data science skills so I'm sure you'll ramp up quickly by being involved in design discussions with the team, learning about the architecture, and not being afraid to ask questions.

cgm42·Nov 16, 2021

Hi Heidi! Thanks for the AWA! Do you have any tips for new developers trying to land their first position?

HeidiW·Nov 19, 2021

Hi @cgm42, there are likely 2 hard parts about landing your first role. The first is getting someone to view your application and reach out to you. The second is about interviewing well so you can get an offer. For the first, I recommend finding ways to highlight your project work (from school/bootcamp or side projects) so that it shows how technically challenging they were or what technologies you learned through them. For early-career candidates, hiring managers are interested in your critical thinking, problem-solving abilities, and ability/eagerness to learn. Make sure you highlight those things in your resume (and cover letter if you do one). For the second, there are various sites that help you practice coding (Hackerrank, LeetCode, CoderPad, etc.) and interviewing (pramp.com). Last year, one of our engineers did a great lightning talk on how to prepare for virtual interviews in particular that could be helpful as well. https://www.linkedin.com/feed/update/urn:li:activity:6760604777027108864/ Interviewing takes practice! Don't be afraid to ask ahead of time about the interview topics and ask for time to prepare for them. It definitely pays off.

cgm42·Nov 22, 2021

Thanks so much Heidi for sharing!

Kerrie40·Nov 18, 2021

Hi Heidi! When building a new platform that's as complex as Grammarly business, did you encounter a lot of bugs, and if so, how did you communicate that to users? Separately, is there some characteristic you've found that you look for when hiring mid-level engineers?

kaylakahl·Nov 18, 2021

Hi Heidi,As you scaled your engineering org, from a hiring perspective, what problems did you come across and how did you address these?

sharonpotsch·Nov 16, 2021

Hi Heidi! Thanks so much for the AMA! As companies look toward the new cost of living adjustment of 5.9% I'm curious how your organization is gearing up for talent retention as it relates to yearly pay increases. Is your organization considering increasing a standard cost-of-living increases or are they considering increasing a standard pay raise to be more in-line with a 5.9% cost of living increase and hopefully retain existing talent? Would love your thoughts on this...thank you so much!

jennie·Nov 15, 2021

I love that you mentioned mentorship for leaders in tech. Where do you find your own sources of growth and mentorship? What has helped you the most in your journey so far?

HeidiW·Nov 19, 2021

Thanks for your question, @jennie! In recent years I have discovered CTO communities and entrepreneurial communities can be a great source of inspiration and fantastic advice from peers. In particular, I've found great insights from some local convenings of Bay Area CTOs, women CTOs and eng leaders, and Peter Bell's CTO Connection (https://www.ctoconnection.com). I am also naturally curious, so much of my growth is learning about the business side of things. I love setting up 1:1s with folks across Grammarly in non-engineering roles to get more context and insights into company, business, and market factors that ultimately impact what products we build.

Princiya·Nov 15, 2021

Hi Heidi, so nice to learn about you, and thank you and Elpha for these office hours.I have a question for you about hiring for diversity. The Engineering team at my company is predominantly white male and the diversity numbers for gender are quite low. We are now looking into revamping the hiring plan, having better training for interviewing, etc. I recently joined this company as EM and I am leading this hiring revamp initiative; there is support from senior leadership team.I understand this effort will take time and effort, but could use any tips and advice from you. Also, any good books, articles, or case studies to read on this?

HeidiW·Nov 19, 2021

Hi @Princiya, congrats on helping your company make progress in this area! I've found an invaluable place to start is Diversity Advocates (https://diversityadvocates.com/). It's a community of folks all driving DEI efforts at their companies with a vast set of resources and recommendations available, regardless of where you are on your DEI journey. They also hold regular events where you can get great advice and make connections with others.

Princiya·Nov 20, 2021

This is great, thank you Heidi for sharing.

leni1·Nov 17, 2021

Hi Heidi!My questions are:1. Is there a good resource for understanding what a Director of Engineering does on a day-to-day that you would recommend? 2. What do you wish engineers who are individual contributors as well as those who are managers would do more that makes you as a Director of Engineering more impactful and effective?Thanks for making the time to do the AMA! Much appreciated.

HeidiW·Nov 19, 2021

Love this question, @leni1! I don't know of a particular place where a Director of Eng role is described, but you can get the sense of it from the talks on CTO Connection (https://www.ctoconnection.com) which I mentioned in another response. If I had to summarize it, Directors of Eng are thinking more broadly than a single team or project and also on a longer time horizon, which also means they need to think more strategically and less tactically. They are also likely working on more cross-functional projects or problem-solving. For example, instead of being hands-on with project execution for a sprint, I would partner with my Product Management peers on annual or quarterly roadmap planning and how to involve the broader team. Or I might be setting up frameworks and processes for helping each of the Eng Managers on my team create and maintain healthy teams. Or I might be creating annual organizational growth plans and then partnering with recruiting to develop a sourcing and hiring strategy. As a leader in the company, I also think about company-wide initiatives like DEI or employer brand or eng-wide initiatives like how to improve quality or building an architectural roadmap. I love when engineers try to think bigger picture and put themselves in their manager's or director's shoes! Come with insights from engineering that they may not see, share where you think there might be technical problems (or opportunities!) that keep you up at night, or even ask them what keeps them up at night to see how you can help! I have an open-door policy and love hearing what's top of mind for engineers. It keeps me grounded and spurs new ideas for where I can help my teams be more effective and ultimately be more impactful!

nataliaohanesian·Nov 18, 2021

Hi Heidi,I'm a founder of a tech startup, we have a strong team but are missing the key position of CTO. I don't have monetary compensation to offer but can offer equity. How do you recommend recruiting for a passionate team member who can lead our app development.

Joanna191·Nov 18, 2021

Thanks for joining us! I'm a startup CEO who just onboarded a very senior VP of Engineering to run our engineering team. He's never been a VP before (only EM) and I've never managed one before. What are some tips you have to create a great working relationship together and set him up for success?

coflaherty·Nov 15, 2021

Hello Heidi! Thank you in advance for offering to answer questions. I work on the product marketing side (directly with product managers and indirectly with engineers) and am curious from your perspective, how do you foster a culture of collaboration with different departments (especially those that may not be well versed with the engineering side)? My past experience has been that engineering teams are pretty siloed and most other departments in a company don't collaborate or communicate with the engineering team as much. What are some ways to combat this? And as someone from a different department/team, what advice would you give to me to proactively try to foster a better relationship with engineers?

HeidiW·Nov 19, 2021

Hi @coflaherty, love this question about collaboration! I find that PMs can be a catalyst or driver for this kind of collaboration, but you don't need to wait for them to set something up :) I'm a huge fan of helping engineers understand the business and go-to-market context and helping non-engineers understand the product and technical context. It helps make sure teams are building a great product that customers want, and it helps align what we build and how we talk about it so that everyone (including customers) is on the same page about what the customer value is! At Grammarly, we have started doing things like roadmap reviews, insights shareouts (customer insights, market research, user research, or data analysis), launch retrospectives, and engineering demos to bring cross-functional stakeholders together with product, engineering, and design. They all leave room for Q&A to foster discussion and help folks get aligned. A good tip is to make sure these are recorded and shared on a wiki or in Slack so they can be referenced later!

coflaherty·Nov 22, 2021

Great stuff, thank you @heidiwilliams26! And I love the tip about recording to post internally.

MaryJantsch·Nov 18, 2021

Hi Heidi! I would love to learn about your progression from Software Engineer at Macromedia to Engineering Manager at Adobe. More specifically, what advice would you give to an engineer looking to move into an Engineering Manager role? I get this question sometimes from software engineers in the Elpha Talent pool who are looking to move into an EM role but are discouraged by job descriptions that require 2-3 years of management experience. Thanks for sharing your time! :)

HeidiW·Nov 19, 2021

Hi @maryjantsch, thanks for the question! It's most common for engineers to become engineering managers within the same company (as opposed to having their first EM role at a new company) because the engineers are already known by the team (both technically and also as a leader or mentor in the team). My path to eng mgmt started because I was interested in learning more about how we make decisions about what features to build and helping feature teams be successful working together and with their PM and Design counterparts. Since I was a known quantity at my company, they were willing to take a chance on me. I became a team lead first, working with a couple of feature teams (usually 1-2 dev and 1-2 QA), and I was involved in team-wide discussions with the engineering manager and other team leads. It was a good introduction to what eng management might entail, so I continued the journey, eventually stopping coding and becoming a full-time eng manager. If there's an opportunity to experiment with a leadership role, mentoring others, driving team projects forward, I highly recommend asking your manager for support in taking on those kinds of responsibilities. I should note, engineering management is not for everyone :) One of my favorite blog posts is by @jkebertz, https://code.likeagirl.io/why-i-left-management-the-engineering-technical-track-vs-management-track-abef5b1d914d, which talks about evaluating how you derive success, where you get your energy, and what motivates you to see whether engineering management would be a good fit for you or not. There are many ways to be a leader, you don't need to be a manager to lead!

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