Office Hours with Jed Brown: On Transitioning from Big Tech to Start-Ups and Back

Jed Brown is a leader of Product Management in Microsoft 365. With more than 20 years in tech and product management, Jed has focused his career on the many ways to understand a customer and understand people to optimize a product and build great teams. Below, we discuss his learnings from both big tech and the start-up world; how to bring your values to your work; and the evolution of product management in the face of industry upheavals including hiring freezes and generative AI.

Kate Danielsen: To start off, in your own words, what do you do?

Jed Brown: Now, at Microsoft, I run a team of 20+ product managers focused on the IT persona for Microsoft Office 365. We are pretty global across Redmond to New York to Europe. We do all of the tooling, including the admin experiences that help IT both learn about the suite of products, purchasing and also deployment. We nurture and grow M365, but in particular, helping them in their growth from their unmet needs discovering the value that exists in the Microsoft ecosystem and in the third-party ecosystem.

KD: How did you find yourself in this role? And please give a brief overview of your career journey and then we'll dive into some specifics.

JB: Yeah. Yeah, absolutely. I’m an electrical engineer by trade and got into Firefox extensions for enterprises to put myself through college, which is how I discovered my passion for what I then learned was product; but specifically, talking with customers. I was learning that I enjoyed understanding customers, being able to take solutions back to the “why,” and build something that would actually deliver on the outcomes they were looking for. That journey led me to Microsoft for about eight years to work across everything from Xbox to Windows to parts of Office. Then I went to startups to do the same thing for two different businesses: one in the telecommunications space, the other in the internal comms space, which is like marketing tools for leadership and companies to communicate well with their employees. That whole time I realized how much I enjoy the business side of product in tech, and really understanding the customer journey from pre-sales all the way to renewal. That customer journey touches everything from marketing to sales to support to customer service, to adoption to upsell and ultimately that satisfaction in renewal that drives really strong customers with high retention and high satisfaction. Learning all of that actually led me back to Microsoft to do the same thing for focusing on the primary purchaser of M365. 

KD: Across that journey, what would you say are some of the most defining moments or decisions that you made to bring your career to where it is today?

JB: The moments that I think have been defining for me are the moments I have been able to be truly people- and customer- centric all the time. It's hard to find a situation where customer focus, people focus, and customer value are always top of mind. Getting things into the hands of a customer is where, to me, that full journey is so meaningful. Expectations are not set when the customer touches your product, they're set way beforehand when they heard about it – and then you have to think about the journey from expectations being set to them actually being delivered. It's a wildly different thing than just putting yourself in the shoes of a customer once they've touched the software. So that real deep customer focus, which is that full life cycle has been one. 

The other, I think, less obvious thing that has taken a long time for me to self-reflect on is embracing who I am and what I enjoy. An example of that is: I think so often, people talk about visibility and building your brand – which is an important thing for many careers, and for different people that can mean different things. For me, I've never been a flashy person, and I struggle to write positive, self-reflective things about myself. Even in review cycles, I like to get things done behind the scenes. I’d rather be known as someone who will always get something done and achieve above expectations – doing things behind the scenes that uplift the people around me, which is kind of my mantra. In the past, I always thought of that as a weakness – that I didn't want to be loud and noisy. But in fact, over time, I've embraced the superpower that being reserved actually can be. That's not to say being loud and noisy is not a superpower in its own right, in fact, I think that helps people accelerate a lot in their career. But it needs to be authentic. And that authenticity of what brings you joy, what makes you feel good or bad, is key in progressing forward. If you think that anything you are doing is a weakness, you might challenge yourself to flip that: how can those “weaknesses” actually enable strength, leverage, or power in yourself – and even more, in the people around you. 

KD: Was that learning curve for you of realizing that your perceived weaknesses could potentially be strengths? And can you point to any specific jobs or projects where you had to figure that out?

JB: Yeah, absolutely. I mean, I think the most difficult situations were the ones that grew me the most. So I won’t say it’s easy, but I’ll also note it’s not hard to be good at something when everything around you is going well. It's when situations are tricky – when things aren't going well – that the true colors of who people are and their moral compasses, or lack thereof emerge. What makes me comfortable when I think of my career and what's next is: I think of it as not just the exciting shiny thing that I want to do, but more so how will that experience help grow me? What am I ready to tolerate next? And I think a lot about that in life: to have nice things, we have to work. To have a nice house, we have to clean toilets and make our beds and sweep the rugs and vacuum –  there are things you need to do to make things nice for yourself. A great meal you cook ends in a dirty kitchen, plates to clean, and trash to take out. The same thing is true of work. There are things that you don't enjoy, that aren’t fun, but that you need to do at different moments in your career when you're ready to create and tolerate change. I've realized that, over time, it's more of a mix than forever targeting the ideal. 

KD: Perhaps an extension of that, or maybe entirely separate: how did you make the decision to go from a company like Microsoft to a startup? And what was that experience like for you?

JB: Well, I think this is both a little bit of luck and privileged opportunities I’ve had together with being deliberate on my side: I've worked hard to not run away from something. And I say that because there are times you need to, but there are also times when things are really good – and that's the time to really evaluate what should be next because you have a clear mind. You start to think about where you could go, which in many cases ends up being where you are just with different, new opportunities or new things for you to do, vs when things aren't great, it pollutes how you think about the future. You end up over-pivoting because you just want to get away from what’s happening right now. The flip is thinking what might be worth your time after coming out of a great success or learning experience. What are those new opportunities and challenges you need?

In moving from Microsoft, a huge part of that was deliberately thinking, “what are the skillsets for the craft of product?” that I didn’t feel I was already doing or didn’t see a clear path to get in the next few years. I wanted to create a line of sight that was closer to the timeline in my head for learning about that, and soon. I actually loved my time at Microsoft, and I left because in that moment I was extremely happy – had been on the best team I had ever been on – and I took the time to think about what clear path could exist for what I wanted to learn next.

Specifically, I wanted to get close to the external, customer-facing finance, business, operations, and sales side, which is what I believe to be a big part of what product does. At the time, we were really focused on building features with engineering and design – which was great, but specifically for me I was a bit farther away from the business groups than I wanted. That’s not true of all of Microsoft – just the group I was working in at the time -- which was a very different Microsoft from what it is today. In reality, that can be true everywhere at any company: your platform or project doesn't have a line of sight to where you want to go in that moment on the timeframe you are looking for. For me, personally, I was looking to go to a much smaller company – a start-up where I would be forced to try on all of these different hats. The goal in my mind with that decision was to try and accelerate my learning in those areas that I felt were forming new approaches to product management.

From the first startup to the second was very different in terms of the type of investors that we had, the type of boards that we had, and the type of product that I was working on: in my journey, I wanted to branch out and focus my career on different targets in the enterprise. I wanted to look at a different approach to product targeting and figuring out a different purchaser. Coming back to Microsoft was for a very similar reason – I wanted to repeat these learnings but at a much larger scale , as opposed to a smaller set of mechanics. So, particularly right now, I’m bringing my learnings from smaller companies to apply what I learned in a bigger way. 

KD: I wanted to ask about the evolution of your role specifically and how you layered in the business approach. Do you think that’s a natural evolution of product management, especially in the time since you’ve been pursuing it? 

JB: Well this probably dates me because when I started my career, program management and project management were the more clear and defined roles compared to product management. So I think my evolution happened in parallel to product management growing and changing. From the early to mid 2000s to now, I was really doubling down on figuring out, “what is product growth?” across both myself and in businesses. In so many cases, it's the product helping to sell itself, to a degree; but it's also actually understanding  the unmet need of a customer. How quickly can they discover, purchase, utilize, and get a return from their investment? The value of that time – that whole journey – is product growth. And it can be assistive with marketing and sales to help scale and amplify what people can do. 

For me to evolve, I was picking deliberately in some cases and accidentally in others places where I could influence and be influenced by marketing and sales. That helps me, the PM, from that presale to renewal. In that full journey I need to feel the responsibility and accountability that what we have in product is matching the expectation the customer has to the value that the customer gets. There are so many people that need to be part of that journey – but the product has to meet the promise from the beginning, and follow up on that promise at the end. 

KD: What have you brought back from the start-up world into your current tenure at Microsoft, and how did that experience inform the way you're approaching your current role?

JB: I think that my start-up experience helped me define the type of role I was looking for and where and how I could help customers meet the expectations from their purchases (ROI). I found a really great role at Microsoft that really touches on core product for a specific audience, but also that full journey of sale to renewal and everything in between. What I've been able to bring forward with me in my new role at Microsoft is challenging myself to apply more product-led growth, and also empathy for all the other roles that sit within Microsoft. The sales team, the services team, the support team and making sure that that is represented in the way that we think about the product-market fit, what we're bringing to the market, and how we're addressing needs for the customers. At the end of the day, everything you do in product affects positively or negatively one of the roles that exist out there that are in constant communication with our customers and the purchasers. Products need to be built with that in mind, that we are humans dealing with and helping out other humans even when we use digital products

KD: What advice would you give to an aspiring product manager?

JB: I didn't believe this when I was first told it, but I'm still going to say it because hindsight is important: having and searching for strong mentorship matters. It’s a two-way street: finding mentors and being a mentor. In many cases, you get more back from being a mentor – you learn so much more when you're helping people. The value of finding mentors, and it doesn't have to be a single, consistent mentor – but being influenced by people external to what you are doing, and being able to ask questions is such an amazing work and life hack. Why I’ve gotten involved in Merit is because it’s a phenomenal way to meet people and hear stories from people with a wildly different set of experiences. As a human, as a father, as a friend, as a hobbyist, the more you search for viewpoints that are different from yours, the faster you grow and it just opens you up. So to directly answer your question, I under-leveraged that (having mentors and mentoring) early in my career, and it took me awhile, but by halfway through my career, I really started to understand that the only way you can build a truly great product is by deeply understanding people’s – customers’ – needs. The same is true for your career. The same is true for life. If you have a narrow viewpoint, then your path is very narrow. If you have a broad viewpoint based on being curious about others, it just expands every horizon. That would be my top advice.

KD: Great, well, this next question is related to what you just shared: how do you incorporate your values into your work?

JB: In every new role I have, I create and send out this really cheesy old school “read me.” I’m very clear about my values, what I believe my role is, how I respond to and act with my team and those around. I think it’s critical to over-communicate these things, because at the end of every day, it's one thing to say you have values, it's another thing to communicate them to those around you and be open to be challenged on which ones do not work, and which ones are appropriate for the situation. That very forward communication of both my expectations and my approach is important. It always just sets things off from the beginning. From there – quarterly, monthly – I self-evaluate whether my values are still true. I actually ask myself and give myself an assessment of whether I’m living up to my values. I think ultimately, I measure values by the impacts they have on the people around me. If it's not positive then they need to change. If it's neutral then they need to change to get better and be positive; and so I hold those to a metric just like I would something we build. It's not about me. The values are gauging how  I operate within the realm of the world around me and make a positive impact. If I don’t see it clearly, it means I have work to do.

KD: Can you give a little bit of tactical advice as to how you actually measure yourself against your values on that regular cadence you mentioned? 

JB: Yeah, and to anyone reading: I'd love to get feedback and improve on this. One of my values is listening before I speak. So I actually ask myself, “how much did I listen before I spoke?” A little bit hard to track but not as hard as you actually think it is. I think even just thinking about that metric in any meeting, right now, changes your behavior to hold your thoughts and listen more before you respond back. When you think about your values, you tend to act upon them as opposed to looking back in the past on. Ultimately, keeping them top of mind in real time is important.

Additionally, I set actual goals that I can measure so that they have influence on me. So for listening versus speaking, it's at least two to one. I work hard to listen twice as much as I speak. That then forces me to call on people – “what do you think about that?” – and get feedback or new thoughts. If I didn’t have this measurement in my mind, I don’t know if my tendency would be to actually do that and call on people who haven’t spoken. 

Another value would be feeling responsible for my team and helping them unblock. So things like responding to an IM or responding to email. I set a specific, kind of old school service-level agreement: I'll respond back in 36 hours. That doesn't always happen, but if it happens less than I've promised it would, I know I need to carve out more time for my team because they need my time. So the value is creating space, which is also something that I actively try to measure, as it’s important for my role. Like everything there are ups and downs, I try not to be too hard on myself but to get back up on the path and push forward. 

KD: Shifting gears: what are some industry-wide or higher level changes that you've noticed in tech recently, and how are they making you excited about the future of the industry?

JB: Two things make me really excited: while it was a bit deflating to see the effect of last year and this year’s hiring freezes and layoffs, it’s energizing to see the after-effect of that, which is the number of people that are thinking differently about what it means to bring technology to different industries and run sustainable businesses. If we look back at other dips in the industry, amazing innovations were born when things were tough. I’ve noticed there is a renewed view of what value actually is and how to evaluate it. Which companies are coming out of these situations with a high moral compass, a focus on people and on their employees. That’s a little bit related to the AI boom. I think everyone's fatigued to a degree with it but I'm really excited about all the different things from old school products to brand new solutions and how they're leveraging what AI can do in ways that just felt like science fiction in the past. I did some recent AI training and a few parts of it just kind of fundamentally flipped my brain, one of those was some research around image recognition on hearts to find diseases. The big insight they found was not any type of image recognition directly, but instead converting those images into an audio wave that you would then run machine learning on to detect anything unusual, including illnesses. It’s just opening up a whole new way to question the norm and rethink how both our digital and analog world can be analyzed differently than it ever has been before. What got us here today will not get us into the future, and moments and learnings like that always get me very excited.

KD: Before we wrap up is there anything that we didn't touch on in the conversation? That's close to your heart or close to your career that you would love to talk about.

JB: Yeah, I think the one topic, just because of remote work and a global workforce has made it more difficult, is that I think we’ve drastically reduced the time we spend with each other. That doesn't have to be physical, that can be a phone call, that can be a Teams or Zoom call as well. But not spending the time on just the thing we need to achieve at the moment, but to learn about each other and what we're working on, what we've learned and what life has thrown at us this week. I think attempts to connect with others have lost some steam as of late. Those, to me, are some of the biggest personal and career growers.

This connects back to the mentorship piece around learning from others – spending time with people actually has the longest term effects on growth in both career and life. When I'm at the office or at home, I try to remember to take the time to talk with people without a specific agenda to ask questions and talk about learnings that don't naturally come up in our day-to-day when we're talking about a specific project or initiative.

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