From Head of Sales and Marketing for 18F to Senior Director of Engineering at Mailchimp – Sarah MilsteinFeatured

Hi Elpha!I'm Sarah Milstein, Senior Director of Engineering at Mailchimp and site director for our Brooklyn office, where I grew the team from 20 to 50+ employees. At Mailchimp, I manage engineers who are senior individual contributors as well as other engineering managers in our growing organization.Previously, I was Head of Sales & Marketing for 18F, a tech-consulting startup within the federal government. Before that, I was CEO and co-founder of Lean Startup Productions, a media startup, and co-author of The Twitter Book. Earlier in my career, I was a freelance journalist writing regularly for The New York Times, co-founded a record label with children’s musician Laurie Berkner, and started Just Food's CSA in NYC program.I hold an MBA from UC Berkeley's Haas School of Business and a BA from Rutgers University, and I was the 21st user of Twitter.Ask me anything about being an engineering leader without a technical background, manager/direct report relationships, cross-functional collaboration, challenges as companies scale up quickly, or something else!
Thank you, Sarah for joining us this week! Please post your questions for Sarah before Thursday. She may not have time to answer every single one, so upvote the ones you’d most like her to answer. Thanks, all!
Hi Sarah, I am currently an engineer and team lead at a software startup and am considering moving into management. If you could give one piece of advice to a new engineering manager, what would it be? Thanks for your time!
As a team lead, you know that a key part of the job is listening to lots of people and helping everyone understand benefits and tradeoffs of various approaches. As a manager, all of that is true--but in a larger sphere. It's not just the project you're working on, but the day-to-day experiences of the people who report to you, their careers, and probably some department or company initiatives you'll work on, too. So the good listening and communication skills you're already developing are really key.But there's another thing that managers typically need: an ability to navigate organizational friction. You'll often hear "no" or unreasonable things from execs, HR and other parts of the business--and it's now your job to figure out how reshape those conversations, not simply accept bad decisions. For example, maybe one of your reports has asked for a raise that you support, but you're told it can't be done. How do you work with HR and other leaders in your department to get it approved--and maybe even change the way the company thinks about raises?New managers often accept nos or unreasonable deadlines without first having deeper conversations to understand what's a hard line, what's not, and how you can influence those things.
Thank you so much, Sarah, this is super helpful! I hadn't considered this area of management, but this makes complete sense and it will be a skill/function I'll need to keep my eye on.
Hi Sarah as a non tech leader how do you best understand project requirements/ deliverables and the age old ‘how long is a piece of string’ question to engineers/developers, of how long will something take to deliver in order to keep teams on track and working together. Thanks for sharing your time and knowledge:)
Hi! I pre-wrote this answer to kick things off, and it got long. I hope all this info is useful! There are a handful of questions about how I do my job as a non-technical leader and manager. I’m going to give context here that will help us discuss some of the other questions, too. First of all, my situation is not unique but it is unusual. Obviously, most people in eng leadership roles have worked as programmers or ops specialists, even for a couple of years; I have not. But my role works out for a few reasons. First, there’s the Mailchimp structure:* Mailchimp has separate tracks for managers and ICs. That means we have senior ICs whose primary role is to advise and guide technical decisions--and my role is really about people management. Before I started the job, I interviewed about 30 friends on managing engineers, and basically, everyone said, “Engineers are people, too!” Which is true; managing people is pretty consistent, with slight variations, regardless of role.* At Mailchimp, the more senior you are as an Eng manager, the less you’re typically involved in the technical details of projects. Instead, at my level, we tend to work on people issues, like setting up standards and systems for interviewing and promotions, or working with other departments to create organizational structures to support cross-functional work. * Mailchimp Eng is matrixed, so the people who report to me aren’t typically looking to me for technical guidance on a project. Instead, they’re looking for help with social and organizational dynamics (how to manage *their* direct reports or a political situation at the company). Then there’s my background:* I have a lot of experience in software development in roles other than programming. So I understand the dynamics of software development (and have strong opinions about them)! That’s hugely relevant to my job and informs a lot of the conversations I have, maybe most of them. * I’m not a programmer, but I’m relatively technical for a civilian. I understand systems at a high level. That lets me keep an ear open for things that are going well or poorly, so I can be a thought partner to my colleagues or tap our staff and principals engineers when I need help. I’m sure that if I had a more technical background, it would be useful and my role would trend more toward technical discussions. In fact, when I was interviewing for the job, I tried to convince people that I wasn’t technical enough for it. But I lost those arguments, and it turns out everyone else was right. So! To your specific question about estimating projects, I have a couple of thoughts. First, it’s not part of my role to make estimates. It’s just not how we’re structured. But it is part of my role to help the people who report to me think about this. So, second, I often bring to bear my experience in software development--asking team leads to think about whether they’re building something to validate a hypothesis about how customers will use our software or if they’re building something that has been validated. If it’s the former, I push them--and sometimes our colleagues in other departments--to figure out how to structure the project to focus on learning from customers rather than on hitting deadlines. Finally, I often help people who report to me figure out how to navigate the organizational conversations about deadlines. There are usually lots of factors that go into somebody asking for a deadline, and we unpack those together and figure out how to tackle them.
Can you recommend any books you found useful as a manager and leader?What do you think is most important to keep in mind when managing an engineering organization?
As a manager, my favorite books include The Coaching Habit ( and Crucial Conversations ( They've both got very good, practical advice for having better conversations day to day. As a leader, I learned a lot from co-founding a company with Eric Ries, who wrote The Lean Startup; that book has helped a lot of people figure out how to better understand--and better serve--customers.But those books are all, I believe, by white men--which means their perspectives are limited. I have learned at least as much critical thinking about tech strategy and workplace dynamics from people on Twitter like Marco Rogers, Sarah Mei, Tiffani Bell, Ellen Pao, and many more. I'd strongly recommend creating (or finding) a good list of people in tech who speak out not only about business trends but also about power and humanity at work.
Thank you!
I really, really like Brave New Work by Aaron Dignan. Here's an endorsement from Susan Cain (The Power of Introverts). "The one-size-fits-all monoculture is a thing of the past. Brave New Work shows us how to embrace the oh-so-human complexity of our organizations—and discover a new way of working that makes room for the many styles, needs, and gifts trapped inside them." Susan Cain
The Advantage, Lencioni. Amazing book, useful and ideal for managing an engineering organization.
I'm curious if, given your non-traditional path into engineering and engineering leadership, you're pushing Mailchimp to invest in candidates with similar non-CS or non-traditional paths into coding (career changers, bootcamp grads, etc.) for technical/engineering roles? If so, how?
Thanks for taking the time to answer our questions.Also, thanks Marie for this question. I am also quite curious about this.
I've been at Mailchimp for just under a year, and when I got here, the company already had both an established apprentice program (to help people try out roles in different departments, include Eng) and a strong internship program (to help people typically early in their careers but often new to tech get into the field). I have a lot of coworkers in Eng who started in Support! But I do think about these issues beyond those programs. The company is based in Atlanta, and I'm the site director for our Brooklyn office, which is just two years old. So we're still forming our culture in Brooklyn, and I have a lot of influence there. We have hired a number of folks with bootcamp backgrounds and/of who have worked as freelancers or as individual programmers in non-software companies. If works in our office, because most of our senior ICs are interested in teaching and mentoring newer colleagues. In fact, in order to better support more entry-level programmers, we've focused on hiring more senior folks with an orientation toward teaching and mentoring. As we have more of those senior people, hired for those skills, I expect we'll start to formalize our support a bit more. For example, we might start a program to have new people rotate through teams as part of onboarding. That might focus on newer engineers but could benefit anyone starting in our Eng department.
Hey Sarah, thanks for taking the time to answer some questions!I've never had a non-technical engineering manager, but I've heard from other engineers that they don't feel their non-technical manager is able to 1) appreciate some of the less "flashy" (i.e. non-UI) work that they do and 2) provide thorough evaluations of their performance because of their lack of technical experience. Admittedly, I too would similar concerns about having a non-technical manager. What strategies do you use to ensure you're able to provide in-depth mentorship and guidance to your ICs? Do you think there are some advantages to having a non-technical engineering manager?
As I explained above, Mailchimp and my role are structured so that I don't typically need to be in the technical details to support my folks. But I'll add some color here:* About half the people who report to me are managers. They usually want to talk about manageering, not technical issues. Their hardest problems are people problems, and I'm a good thought partner for those.* The ICs who report to me are staff and principal engineers. Most of their hardest problems are people problems, too (how to influence other team members or how to handle conflicting requests from execs, etc.). Again, I'm good to go on those. * When technical issues are really central to a problem, I tap other principal and staff engineers to give advice. They're also a good resource for pairing with and giving feedback to engineers who want evaluations of their work. I strongly encourage people who report to me to talk with other folks regularly. * When I do reviews, I ask around a lot (with full knowledge on all sides) to get more perspectives. That's baked into our matrix structure anyway. * I ask tons of questions about technical implementation, and I sometimes ask for a tech explainer in which a couple of engineers will sit down and walk me through how our databases work, or our relationship with cloud providers, or how we've structured our public APIs. That doesn't help me read code, but it helps me have relevant conversations with folks.* I do understand software development! In my role, that's often a lot more important that technical details, because it always involves other people--who are usually a problem. :) I help the folks who report to me figure out how to navigate those issues.Most of the time, I'm a good listener, which is the really critical management skill. It means I can tell when somebody needs help outside my expertise, and then we can figure out together how to get whatever they need. I hope that helps explain how this can work!
The more I hear about different team structures the more I understand the need for a clear IC/manager split, and your first point about "their hardest problems are people problems" particularly struck me. It sounds like Mailchimp has a lot figured out in terms of org structure/career advancement and the review process!This and your other replies really helped explain how this can work and what it looks like at Mailchimp. Thanks for leaving such detailed responses!
I'm curious to hear how your sales and marketing (and writing) background has helped or hindered your current work in engineering? How did you end up in your current role?
In my role, it’s hugely helpful to have perspective from different parts of business. As a senior leader, I'm expected to understand and influence a lot of areas: my direct reports; projects that I advise; department operations; cross-department collaboration; company initiatives; and my local office (Mailchimp is HQ'd in Atlanta, and I'm the site director for our Brooklyn office). Having a broad background help me quickly learn and contribute to all of those things. For example, it's not hard for me to understand how our partners in the marketing department see things, which can help me have better conversations with them. Having a writing background means I have deep experience thinking about how other people will understand what I say. As a leader and manager, communication is at least 80% of the job, so that feels relevant all the time. I have to admit that if there are ways my other roles have hindered my current work, I’m not aware of them! The short answer to how I go the job is that a friend inside Mailchimp recommended me for it, and I believe, advocated for the company to take bit of a risk in hiring a non-engineer into the role.
Hi Sarah and thank you so much for being available to answer our questions :)I admire strong and successful women they are role models to me!!What I would like to ask you, regards your previous experience as the Head of Sales & Marketing at 18F. My studies are on Computer Science and in the past I have held both technical and business roles. Recently I have taken over the role of business developer for a successful bootstraped company and I want to master this role. How could I get educated/trained/informed on BizDev techniques? Searching online seems like the educational material is limited (or at least I didn't come across something worthy) and I am not sure how to navigate in this domain? Thanks in advance! <3
For biz dev at different companies, I have twice hired experts to consult with me and my team and help us level up. That paid off *enormously* in both cases. I highly recommend investing in that kind of coaching. (Bonus: both consultants were women.)
My question is what, according to you, are the mistakes companies make while scaling up or growth hacking?
My question is: What advice would you have for engineers coming from nontraditional backgrounds? What skills should they develop to stand out among peers?
Thank you for answering these questions! I am curious as to how you were able to convince others that being a technical leader was a good fit for you and also how you manage the skepticism from technical staff that may report up to you.
Hi Sarah, Thank you very much for this AMA!!As you're leading the team of Enterprise developers, I'm curious to know, 1. What are the big 3 problems enterprise dev faces while in development?2. How enterprise developer manage/collaborate with each other when working with multiple technologies/concept/libraries while development?ie. Some team working with APIs, some of are with GraphQL, Some are with IoT and some of are with Realtime ( Websocket, Ably, Pusher)
Thank you! I am having such a difficult time finding a female full stack developer. Do you have any leads or recommendations? I am developing an app that makes women the experts on their bodies and a man CANNOT build that!