Office Hours: I'm a Director of Engineering at a Series C stage startup. I'm Jossie Haines.Featured

Hi everyone!I’m the Director of Platform Engineering at Tile. We are empowering the world to find what matters the most by creating Bluetooth location finders you can attach to anything from keys to turtles! I spearhead all aspects of partner integrations throughout product development lifecycles, including solution design, development, testing, and launch to market. I also lead our diversity and inclusion initiatives and started our mentorship program. Before joining Tile, I was an engineering leader at Apple, Zynga and American Express. I’ve always been passionate about consumer facing technologies and technology that works at a large scale. My tech career started at a now non-existent dotcom startup in early 2000 after falling in love with the Bay Area. I have a BS in Chemistry from Princeton and an MS in Computer Science from UC Santa Cruz. I didn’t realize I wanted to be a software engineer until after my undergrad degree while I was a technical consultant for PricewaterHouseCoopers.Ask me anything about leading engineering teams, transitioning from being an individual contributor to being a manager, my approaches to making Tile an inclusive workplace, how leading with empathy can truly empower belonging or anything else!
Thanks so much for joining us @jossieHi Elphas! Please reply in the comments with your questions and @jossie will be answering them this Thursday. She may not have time to answer each question, so please emoji upvote the ones you're most interested in. Thanks!
Hi Jossie! Two questions for you1) I imagine you've worked with your fair share of Product Managers over the years. Of the best ones you've worked with, what have been the characteristics that made them so great? 2) What would you tell someone who thinks they are interested in becoming a software engineer? Are there particular programs or resources you recommend? Or ways to confirm this thought? (spoiler: this 'someone' is me)
1) Product managers who treat engineering as their partners and really lean into the relationship. Taking the time to loop engineers into product direction as well as being technical enough to understand at a high level how the architecture works and what the big gotchas are. I also value product managers who really take the time to listen to engineers and realize that we are working towards the same goal of building a better product.2) I'd love to know more about why you want to be a software engineer to lead you in the right direction. Have you tried coding and love it? Is it just something you're more curious about? Do you like the idea of sitting at your desk coding most of the day? Would you prefer a role that's more half and half like a developer relation role? I'd suggest thinking about some of these questions as well as dabbling in a little coding yourself. If you enjoy user interfaces and working on the front end you can look at Javascript or React (I love the Road to React book). You could also look into backend technologies like Java if that's more to your liking. Or even look at data engineering if trying to solve data problems is what excites you. Look at different technologies and see which one peaks your interest.
1. Love that you said that! As a PM, I feel like this is also critical. I've heard from other friends in tech that historically eng and PM relationships can be strained but I find that engineers are my favorite people to work with.2. Thank you for the advice! I feel energized by it. To answer your question, I've always taken a lot of satisfaction with making something from nothing with my hands. Usually this is manifested in creative projects but I often found myself jealous of that feeling of satisfaction engineer gets. I learned SQL last year and found it very empowering and definitely want to dig into that interest further.
Yes, the satisfaction of producing something with code can get addicting :) Even though I don't code on a day to day basis any more, during my vacation last week I still coded for an afternoon cause it was so much fun to test out a new technology and make something new. There is so much you can do with SQL, and as a PM it can actually be a very powerful tool. You are usually dependent on the analysts to help you gather metrics for your projects, but by having that knowledge you can feel empowered to make your own conclusions and analyses!
What advice do you have for someone who isn't technical looking to hire a director of engineering as one of the first roles? What should the characteristics be for the first engineer hire?
Hi Kathryn -- I'm assuming this is for a small company which may have a couple engineers. Find someone who is willing to be hands on and still get into the technical architecture, but can also effectively communicate with you about technical challenges. Look for someone with passion for mentoring others and understands that engineering leadership will be fluid and the processes needed when you are a couple people will not be the same you need when you have 20 engineers. They should have a learning and growth mindset. Try to find "T" shaped people -- someone who has deep technical knowledge or experience in one thing, but is also a generalist and doesn't mind jumping into different things.Good luck with your first engineering hire!
Hi Jossie. Thanks so much for your very thoughtful response. :)
Thx for tkg questions Jossie; I'm working on something that requires a ground-up reengineering of the way things are currently being done. It's a massive project as such, and yet it needs to be done as the way we're doing it is unsustainable (its reinventing the online shopping process). I'm a non-tech founder and in Houston (where you can't find CTO's on every corner). Where would you start with limited capital? Outsource for the MVP? Tysm!
Hi Jo! What is your most important objective? Do you want to find a technical co-founder who you can partner with for the long term to figure out some of the technical foundations needed to reinvent online shopping or are you looking to create an MVP to prove out your idea and get funding? If you outsource the project you also need to be prepared that the code you get may not be the most extensible to build on -- again it's always going to be a balance between the three things: time, price and quality. Given the shift to remote working with covid-19, you may also consider finding a remote CTO or technical co-founder and really consider if you do need someone there in person. You can also find technical experts who are willing to be consultants for small companies just starting and can help you through the process - this would most likely be more expensive than getting a co-founder or getting an MVP built though.If you're looking for something quick to prove something out then definitely do the MVP. If you're looking more for someone with technical knowledge who you can brainstorm with and will really gel with you for the long term it will take longer and I would be more thorough about the search. You can see my reply to Kathryn in this thread for things to look for in that first manager hire.
Thanks so much. My first choice would be to find a technical cofounder who believes in the longer-term need for this reinvention and who would be willing to code the MVP for sweat equity even as a side project initially. That said we can’t always get what we want and secondarily I would look at outsourcing the MVP but again yes, the code is then probably something you would end up having to rebuild some point when you do find a longer-term CTO. I also don’t care at this point if the co-founder is local… But I do think it could be harder if they are overseas. Thx again Jossie
Hi Jossie!I'd love to hear more about what you look for in your new hires, after having transitioned from being an IC to a manager. What's more important to you -- experience in a specific tech stack or soft skills? Do you have a systematized approach to hiring? I look forward to learning more about your thought process.
I could write pages about hiring but I'll try to stay concise :) To answer your first question: tech stack or soft skills? For me it's about both. And if they don't have the right soft skills, I don't care of they are the god of programming -- I won't hire them. Why? I stick to a no assholes rule -- I've spent enough time in my career cleaning up the team drama and morale issues that are caused by brilliant jerks to put up with them. I look for people who are empathetic and want to collaborate to produce the best possible product -- not just for their ego. Tech skills are important to and it's important to really figure out what the "must have" requirements for your roles are. As you may know, women only apply to roles if they meet 100% of the requiremetns, so if you have a long list of requirements you may not end up with a very diverse pool of candidates.This ties into your second question about having a systematized approach to hiring. I think this is important because there can be so much bias in the hiring process that you need to ensure you are creating a fair hiring process that reduces or eliminates bias. There are a ton of different aspects to this but some high level ideas are:-- do you have a set of questions you ask every candidate for a specific role-- what is the bar you are trying to hit and how do you clearly define it ahead of interviewing-- Are your interviewers trained in interviewing and know how to ask questions, collect feedback and reduce bias in their evaluations -- Do you look at stats around diversity both gender and ethnicity of your hires through the process and in your team Always be thinking about who you need to hire in the future and be networking and finding potential candidates. You may not have a job opening today, but if you know you'll have one in 6 months can you start lining up people through networking who may be potential hires or know people?Check out for more tips and tricks around systematizing the hiring process specifically around diversity.
Thanks so much, @jossie I especially love this advice. "As you may know, women only apply to roles if they meet 100% of the requirements, so if you have a long list of requirements you may not end up with a very diverse pool of candidates."I totally agree with the systematized approach and set questions. We do that with our internal hiring and it makes a HUGE difference -- reduces bias, randomness and takes a lot of the pressure off of hiring managers. Thanks again!
Hi Josie! I’m a mid career changer going from growth marketing to software engineering. I just finished a coding bootcamp and am looking for my next opportunity in this market. Do you have any advice for us new grads on how to navigate this market? Also, I currently have an eye towards engineering management/leadership as my long term goal. What are some things I can do early in my career to prepare myself and also assess if that’s the right fit for me. Is there a minimum amount of time you recommend one should spend as an IC before considering the jump to management? Lastly, what are the qualities you look for when hiring or promoting ICs to engineering managers. Thank you!
Hi Azra, Check out the answer I gave to Leia here: which will hopefully help you navigate this market.My biggest advice is don't jump too soon and be sure you want to manage for the right reasons. While I don't have an explicit amount of time for how long to be an IC, you want to be one long enough so that you've seen a wide variety of technical challenges, and you have a deep solid technical knowledge in one area and have really developed the skills to think higher level about systems and architectures. If you jump into management too soon without these, it's really hard to gain deep technical knowledge when you aren't coding day in and day out. You're also going to be in the code less and need to be able to still ahve those technical conversations with your employees. As for making sure you want to manage for the right reasons I suggest taking the time to reflect on what interests you about being a manager. As a manager you'll be rewarded not for what you produce but by the success of your team. The most successful managers are those who truly want to help others thrive. When promoting managers I make sure they have the technical depth they need as well as empathy for others. I look at whether they are able to give crucial feedback. I reflect whether they can think big picture and really understand how to work with product to turn a product into reality. The skills that will make you successful as a manager are different than those as an IC and that tends to be one of the hardest parts of the transition for people. So you can get ahead by starting to build those skills early.
Thank you for the advice @jossie! I've managed people in the past and have found guiding and developing my reports to help them succeed incredibly rewarding, which is I'd like to eventually explore management in engineering as well. Agreed, re: not making the jump too quick and noted re: the skills you look for when promoting from IC to manager.
Hi Jossie, thanks for participating in office hours! In your experience at hypergrowth companies, what has been the biggest challenge (either from a management perspective or technical perspective) of leading your teams in rapid growth environments?
I think the biggest challenge is realizing that the engineering practices that work at 20 won't work at 50, and then you'll need to change again at 100, and so forth. While the exact numbers I listed are hypothetical breaking points the main point is that as your team grows in size the processes and policies you are using are going to need to keep evolving as the team grows. You need to ensure you're hiring people with a growth mindset that also align with the company culture. That alignment with culture may seem like something to discount when trying to onboard a lot of talent -- but this can be a big future downfall if not focused on as well.
Thanks so much for taking the time, Jossie! What advice would you have for a junior self-taught web developer who was just laid off from her first technical job (at a startup) because of COVID, and now has to job hunt?
Hi Leia, Thanks for reaching out and asking this question. I can imagine how hard and scary it must feel to be trying to look for a job right now. I've lived through the dotcom bust and the 2008 recession, and things will eventually get better even if it doesn't feel that way right now. My first piece of advice is to focus on concrete short term goals. Set aside a least an hour every day to look and apply for jobs and another hour every day on personal development. There's a lot right now we can't control, so focus on what you can control.Things right now are tough, and it may take some time to find a role. Resilience is something I think is so important to build as a woman in tech, and during this situation it's more important now than ever. Resilience is built through small actions every day -- what's something that scares you that you could work towards?Next take the time to build your personal brand and define what makes you unique. Make sure you are sharing your strengths. One of the best ways to retain knowledge is to actually share that with others and teach it -- so can you write articles or create videos about some technology you are passionate about? Remember, while you may feel you don't have anything to share, there is always someone who knows less than you do -- if you just learned it, there's someone else out there who doesn't know it. Kapor Capital also created a great new job seeker covid-19 resources guide with a lot of great info that I hope will also be helpful. You can find it here:
Hi Jossie! Do you have any advice for someone who is on the job hunt and doesn't have an immediate network of people I can go to to ask for jobs? What are some tips I can use to make new developer friends? Where are some places I can find other people and work on projects together? Thanks so much!
Hi Michelle -- well you joined Elpha which is a great place to start! Instead of approaching people on linkedin with the intent of asking them for a job, what if instead you ask them something interesting about themselves or their career? People are much more likely to reach out if you want to engage in a real convo instead of just being asked for a job. Even though we aren't going outside right now, a lot of meetups are moving online and virtual. Can you find a meetup related to a technology you are passionate about or interested in? Can you find an open source project looking for contributors? There are a number of great developer communities: is a great dev website, Coding Blocks is a developer related podcast that has a very active developer slack channel, and there's Women Who Code that has technical focus areas with conferences as a few starting suggestions.Good luck on your job hunt!
What advice would you give someone managing teams who's looking towards the Director level as next step? Moving from managing ICs to managing managers seems like a gap nobody really talks about.Second question, how do you balance being a champion of diversity and inclusion against your accountabilities in Engineering? What does your leadership do well to support this, that others could learn from?
Moving from managing ICs to managing managers ends up really stretching our leadership skills and certain skills end up being even more crucial like giving critical feedback, knowing how to gather the information you need to be successful without being a micromanager, learning how to really coach rather than tell, and finally just figuring out all those instinctive things that you do as a manager that make you successful that you now have to figure out how to coach in others. I enjoyed reading the Manager's Path which did cover the transition into managing managers. Here's some high level tips for the transition:- learn to say no and value your time - create focus time on your calendar to work towards your goals - set concrete goals you want to achieve -- this can get you out of the rut of feeling all you do is go to meetings - take time to reflect on what you're strengths are for managing ICs so you can share that knowledge with your new managers As for balancing D&I and my engineering tasks -- it's definitely hard :) D&I is my passion and really my hobby as I volunteer a lot of time mentoring, holding office hours, and doing public speaking on top of leading our company D&I initiatives. What I really look for from my company is the support to let me do those things with the knowledge that they know I'll deliver on the engineering tasks and deliverables that I've committed to. It's really having mutual trust and respect. No one asks me how much time I spend on one versus the other. Tile also realizes this is a benefit for them at the end of the day -- I'm helping grow other leaders and individuals within our organization as well as getting the company's name out there as one that truly does care about creating a true culture of belonging.I am also highly disciplined with my time management and scheduling too though -- I've been focusing a lot on what I really want to say yes to, and saying no to other things so I can prioritize what is important on all fronts.When I was interviewing for my role at Tile, I spoke w/ Lissa and CJ, the VP of People and our CEO and told them both if they wanted me as the director of engineering for platform, I also wanted to run D&I too and start a mentorship program. They both supported me and loved the idea and here I am almost 2 years later loving what I get to do every day because I get to balance my mission with keeping women in tech with my drive to build amazing technical products that change the future.