Gmail’s user interface. Facebook’s Newsfeed. Twitter’s timeline. Dropbox’s bottom-up revenue engine. In his 15-year-career, Todd Jackson has helped build some of the biggest products in tech that hundreds of millions of people use every day. He’s been the pivotal PM in hypergrowth, the seasoned director charged with redesigning critical features and the steady executive steering his team to IPO. But he’s played other parts as well. At his startup Cover, Jackson was the scrappy co-founder and CEO navigating the challenges of fundraising, product/market fit, and an acquisition. He’s also been an angel investor, veteran advisor and first call for dozens of early-stage consumer and SaaS startups.
And as we’ve just announced, Jackson’s about to take on another role. He’ll be officially donning the investor’s cap and joining us as a Venture Partner here at First Round. Given that a new year and new job marks the perfect time to reflect on standout moments, we sat down with Jackson to tease out takeaways and mine some stories from this stellar trajectory. While he’s shared some now-classic reads on vetting PMs and building hot products on the Review before, this time we wanted to zoom out a bit as he makes the transition to full-time investor.
That’s not to say this will be in the mold of VC armchair advice or the sometimes halfhearted (and certainly hackneyed) “Let me know how I can be helpful” catchphrase. If you’ve been a regular reader of the Review over the past seven years, hopefully you’ll know that’s not quite our style. From the very beginning, we’ve been laser focused on sharing actionable startup advice from the best practitioners — the ones who’ve actually been in the trenches building.
And Jackson certainly ticks that box, which is a key reason why the First Round partnership was eager to bring him on board. Whether you’re an aspiring entrepreneur searching for a startup idea, a scrappy team chasing product/market fit, or a more seasoned exec pushing through hypergrowth with an eye towards a future IPO, he’s been in your shoes very recently. In this exclusive interview, Jackson shares the most pivotal lessons, frameworks and processes he picked up as he tackled challenges at every startup stage. Organized into a punch list of four tactical takeaways, his advice for current and future founders is spot on — and it’s still fresh from the operating trenches. Let’s dive in.
Curious about to learn more about First Round approaches adding partners and why Jackson felt this was the right career move? Be sure to check out his recent interview on the Twenty Minute VC podcast with Harry Stebbings (and fellow First Round partner Phin Barnes).
Jackson’s Silicon Valley career started at Google in 2004, where he joined the second class of the now storied Associate Product Manager program. And while he went on to serve as the PM of Gmail for five years (leading it from beta to more than 200 million users), what stands out most from his long stint at the tech giant was the product building firepower that he was surrounded by in the early days.
“I shared an office with my boss, Marissa Mayer, and I sat down the hall from folks like Bret Taylor and Justin Rosenstein,” says Jackson. “It was just a special time to join the company. Google Maps, GSuite and the cloud platform didn’t exist yet, and even most Googlers didn’t use Gmail at work — everyone was still on Outlook. So from the ground up, I got this incredible inside look into how the best leaders at Google approached product development.”
If he had to distill that experience into a single takeaway for founders and product leaders, it would be this: Building really high-quality products takes an incredible amount of behind-the-scenes discipline, especially as your team grows.
“Most founders start off with an intense focus on product excellence. But as the product and feature set expands, strategy starts to drift, bloat creeps in and the user experience degrades significantly,” says Jackson. “In practice, I’ve found that you can make sure that discipline remains front and center by identifying and then obsessively focusing on the two to three most important qualities of your product. At Google, those qualities were speed, simplicity and power.”
To illustrate how that focus on those qualities worked in practice, Jackson shares tactical examples from his time at Google:
“Marissa Mayer’s UI review meeting still stands out as one of the most rigorous internal processes I’ve ever participated in,” says Jackson. “Every week, you’d put new product mockups in front of her and a committee of senior designers, and she would inspect every page and pixel. The feedback could be withering but it worked.”
Jackson remembers one session in particular where he brought a prototype in for review and Mayer told him it was too busy. “Marissa told me to go back and add up a point every time I used a new font, font size or color — and that the entire page needed to stay below five points before it could ship,” he says. “She was incredibly rigorous in how she approached building simple products, and I couldn't help but pick that up from her.”
His experience working on Gmail was similar. “The Gmail engineering team was badass, and they wouldn’t tolerate a bozo PM trying to push out half-baked features. Over five years as Gmail’s PM, I learned how to design features and refine them over and over, so that they kept the experience lightweight and fast,” says Jackson.
“The bar for launching a new product or feature was incredibly high. Anything that wasn’t simple, powerful, and performant wouldn’t go out. I’m not joking when I say that we held up projects at the 11th hour because we’d inadvertently made an action 30 to 40 milliseconds slower or made the experience slightly more complicated.”
The best product leaders I’ve worked with have a laser focus on quality and a steadfast willingness to make sure things don’t regress. Every feature launch requires a staunch protector of the user experience. Don’t have one on your team? You just got a new job.
But product leaders and founders also need to make a habit of stepping back and evaluating these attributes from a higher altitude. “Sometime around 2009 or 2010, Larry Page was fed up with how long all the GSuite properties were taking to load. Lots of web-based products go through this as they grow,” says Jackson. “The combination of tons of new users straining the servers, and — surprisingly more often — the growing team of engineers, PMs and designers who are busy adding features and code to the product can start to take a toll. It’s a tragedy of the commons. If you’re not constantly vigilant about performance, your app can get bogged down.”
Many try to carve out time for maintenance and paying down technical debt while still forging ahead on ongoing innovation work, but Page took a more radical approach. “He basically said he’d had enough, and put every single Google app, from Gmail to Docs to Spreadsheets, on a complete feature freeze until all the apps loaded in one second. It didn’t matter what new bold idea you were working on, your job was now to improve performance. Entire quarter-long roadmaps were put on hold,” says Jackson. “So even as PMs and designers, we started helping out on performance-oriented features. This was the genesis of features like the background attachment uploader and the loading page you see when you first open Gmail. We had actually just added the loading page for ourselves at first for debugging purposes, so we could see where in the loading sequence things were slowing down. But then users seemed to like it so we just left it in, and it’s still the same today,” he says.
“At the time Larry’s mandate felt a little discombobulating and maybe seemed extreme, but looking back, I’m impressed to the degree with which he was willing to say ‘Speed is our most important feature, and all of our internal development processes are actually eroding it, so I’m just going to bring a hammer to the problem if that’s what’s required.’”
So does that mean that stop, drop, and focus on speed (or any other product feature) is always good advice? “You can’t hit the emergency brakes too often. This is the kind of leadership technique that needs to be used sparingly,” says Jackson. “But when invoked, it can be a powerful way to get everyone rowing in the same direction very quickly. The simplicity of the mandate was key — hundreds of people in the organization could immediately see what needed to be done.”
As an angel investor and advisor to many startups, Jackson enjoys the cadence of meeting with founders and their heads of product every few weeks. Their sessions typically cover what he calls the two critical pieces of product:
Product strategy and getting to product/market fit
Product development and running an effective internal team as the team grows (diving into goals, roadmaps, milestones and metrics).
“Probably the number one question I get asked is how to find product/market fit. But before we dive into frameworks or specific tactics, I always ask budding founders to back up. Because when it comes to finding product/market, the most important choice you make is the one before you get started — when you identify the right market to go after. Aside from choosing your co-founder, it’s the single most important decision a founder makes, and it’s one too many get wrong,” says Jackson.
A more specific pitfall he often witnesses is that many product managers-turned-founders dive straight into execution mode. “They think of an idea, move quickly to building a prototype and then sometimes momentum and the excitement of building takes over. While the operational focus and pure execution that you picked up as a PM are huge strengths, you’re better off first taking a step back and thinking about whether the market you’ve chosen and the problem you’re solving is big enough,” he says.
Which begs an obvious follow-up question: How can founding teams tell if a startup idea is worth pursuing? When Jackson left Facebook in 2012 to take the entrepreneurial leap from big to small, he was facing that exact predicament. “My co-founder Ed Ho and I knew we wanted to do a startup. We knew we worked well together from our time at Google, and that we were really interested in the same consumer spaces. But what we ended up pursuing — what became Cover for Android — was actually our third idea,” Jackson says.
“Our first idea was in the sports space. We designed some things, talked to a bunch of entrepreneurs who had done sports related stuff and we realized that it was a hard market to compete in. Our second idea was a photo sharing app. At the time, Instagram was popular but not dominant, and Snap barely existed. There were still a lot of interesting things I think to be done there, but ultimately we were talked out of it by investors who were like, ‘Even if this is the next great photo app, how are you going to convince anyone of that? Not just users, but the engineers you need to recruit and so on.’”
To pressure test ideas like these (and the one that eventually one out), Jackson and his co-founders relied on the following framework — one that he still coaches future founders through to this day.
Functional needs: Does it address a clear functional need that users have? This is often why they’ll try it.
Emotional needs: Does it address an emotional need that users have? This is often why they’ll tell others about it, unlocking that viral word-of-mouth growth loop that’s so critical.
Billion-plus market: Is it in a large, underserved market? Or in a market that can become large? This impacts everything from your ability to fundraise to who may be interested in acquiring you.
Breakthrough UX: Is there something novel or unique about the user experience? Does it feel a little like magic when you use it? This last one isn’t strictly necessary, but it’s very helpful, and a lot of successful products had it when they launched.
“Most founders I talk with haven't thought about their idea this deeply. They have a high-level problem they want to solve, but haven't yet mapped it to the functional and emotional needs of their customers. If you don't go through an exercise like this, you’re in danger of developing a nice-to-have product, not a must-have product — which puts product/market fit further out of reach. This exercise forces you to name the needs, and then pressure test whether those needs are acute or if they're just nice-to-haves,” says Jackson. “The functional part is usually more obvious, but the emotional component can be tricky. Your customers generally can't or won't name it themselves. You have to probe on what they feel and translate what they’re saying into a product.”
If you think of ideas that simultaneously meet people's functional needs and emotional needs, while sitting in a big market and making use of a breakthrough user interface, that’s a recipe for a really good company.
Below, Jackson runs us through a few quick examples of this framework in action:
Instagram: “It’s easy to forget, but in the very early days, back around 2010 or 2011, a lot of people liked the functionality of easily being able to get photos from their phones onto Facebook, Twitter, Tumblr, and other networks at once. Emotionally, the filters made your photos look cool (so you felt cool posting them) — especially in the early days when the iPhone camera wasn’t as good as it is today. There was also clearly a very sizable market as mobile phones became ubiquitous and camera quality steadily improved. Finally, the one-tap filters UI made Photoshop-esque editing accessible and easy.”
Glide: “First Round invested in this team last year. Glide allows you to create an app from a Google Sheet in minutes. There’s the functional need of creating great apps and mobile experiences more easily. The emotional need is that it takes something that felt off-limits and turns it into a sense of creative empowerment, that you can build things without a super technical background. And I think we’ve seen from examples like Webflow that no-code products have a potentially huge market behind them. Finally, the breakthrough UX is the spreadsheet to app process — truly feels like magic in action.
Cover: Finally, his own startup: “Functionally, we gave Android users a simple way to organize their apps, and replaced the clunky Gingerbread stock UI to make their lockscreen sleeker and smarter. And by specifically building for Android users, we tapped into their emotional needs. They often felt like second class citizens. ‘Only available on Android’ became a rallying cry for hardcore users to share the app and feel proud,” says Jackson. “Additionally, Android was a monstrous market, but it was also massively underserved — almost no Silicon Valley companies focused on it. Most startups treated it as an afterthought to the iPhone. Finally on the UX front, a lot of Cover’s features and design ideas were quite novel at the time.”
Of course, staying focused on those functional and emotional needs as you build the product requires some heavy lifting. “Even with a thesis in sight, you need to put in the legwork to make sure you deeply understand your customers. I talked to hundreds of Android users, using tactics like recruiting people on Craigslist and setting up a user research table inside a Starbucks,” says Jackson.
“A lot of what I heard is that they wished they could upgrade their phone to something better — without paying more for a new phone. Once we had those core needs identified, we designed every single feature of the app to serve them. We iterated a bunch with a core beta community, and when we released the app publicly, it grew very quickly. Word of mouth was really strong, because of that emotional connection. We grew to over 2 million users in the first couple months with zero money spent on paid acquisition.”
Navigating acquisition offers is another thorny challenge that founders can face. There are several uncertainties swirling around. Should you sell or forge ahead hoping for an even bigger outcome down the line? Who should you sell to? What will life after acquisition look like?
Jackson opens up about his experience selling his own startup to shed some light: “With Cover, we were approached by about a dozen companies, all of whom felt they knew how important Android was, but didn’t have internal expertise in it. The story that we were getting was ‘We know that Android is huge, but we don't understand it. Why don't you join us and be our Android strategy?’ That was the pitch,” he says.
They opted to sell Cover to Twitter in 2014, joining to lead the social media platform’s Android efforts. “In hindsight, it might seem like the surefire move. We sold when the market was hot and we landed in a good place at Twitter. It was a great outcome for the team and our investors. And in the back of our minds we had some worries about the long-term viability of our approach as a startup, as we were so reliant on a single platform that was owned by another company,” says Jackson.
“But we were growing fast and we had most of our seed money still in the bank, so we certainly could have plowed ahead. And of course, there was still that twinge of regret, that we didn’t go really big. Joining Twitter shifted our own personal dreams and plans in a big way. That’s why it wasn’t a unanimous decision among the founders to sell at first. As our investor and board member, Josh Kopelman really helped us navigate this, and eventually we all agreed that an acquisition made sense. And I think I’d still make the same decision today.”
Here, Jackson dives into two takeaways from navigating his own acquisition experience, which he frequently shares with founders navigating a similar choice:
The process. “We drove the timing and created competition across different potential acquirers. And we kept all of them on roughly the same schedule. We told them we weren’t looking to sell the company, but we owed it to our employees, investors, and ourselves to be open to discussions. But in order for it not to distract us, we wanted to contain all discussions to a three-week period, and at the end of that period we’d decide whether to sell or not,” says Jackson. “So we ran it almost the same way you’d want to run a fundraising process as an entrepreneur.”
The aftermath. “The main thing I try to communicate to founders who are thinking about being acquired, is that an acquisition sounds glamorous when it happens, but once you’re acquired, your role is to work in service of the larger company that you’re now apart of. The story you were told, and the strategy that went into the acquisition can change if the needs of the organization change. And that’s what happened to us,” says Jackson. “As part of the acquisition, we were brought in to lead Twitter’s Android strategy and execution, and we spent the first few months doing that. But soon after, my co-founders and I were all pulled in separate directions internally. I was asked to lead product for Twitter’s Content & Discovery team, while my co-founder Ed was asked to lead engineering for the client platform teams. So while we ended up having a big impact, it wasn’t in the way we originally envisioned. And that’s what you need to expect,” he says. "Outside of these shifting priorities, Twitter was certainly a bit of a rough ride. But at the end of the day, I’m glad I have it in my history so that I have some first-hand knowledge to coach founders with.”
In 2015, Jackson embarked on another challenging experience when he signed on to join Dropbox as the company’s first VP of Product & Design in the lead-up to its IPO. “Dropbox was maybe the most intense job I've ever done. It was even more intense than being a founder, which really surprised me,” he says.
“In the early days of being a founder you're completely in control of your own time. Nothing’s working, you’re desperately trying to build a product and recruit people and keep all the balls in the air, but at least it feels like you’re in the driver’s seat. But, if you’re lucky, there comes a point when the rocketship starts to take off and you go from running things to things running you. The two to three years before IPO are the most intense for a company. As you march down that path, expectations from the board and investors are so high. You’re being heralded as the next decacorn, even if it doesn’t feel like the company is internally operating at that level yet.”
After coming out the other side from this experience, Jackson’s eager to help founders put in the legwork needed to place themselves on better footing. “My biggest takeaway from helping a multi-thousand person company prepare for an IPO is that you need to deeply understand, refine, and articulate your product strategy and revenue growth model, years beforehand,” he says.
“Make sure your product strategy accounts not just for how you’ll expand your current business, but how you’ll compete in new markets as well. It also needs to tie very clearly to your go-to-market playbook, so that your growth becomes predictable. That’s what the public markets really value — and that’s how you can learn where the levers are in your business. It's not enough just to have a business model. You actually need to be able to predict and forecast that business.”
Trying to get your shit together for an IPO is impossibly hard. Start as soon as you can, by clearly articulating your strategy and using it to drive your internal capabilities and systems.
“Dropbox was one of the first companies to define what’s now known as bottom-up SaaS. But that wasn’t fully in place when I joined in 2015. The majority of our revenue was coming from individual consumers, not businesses. We knew this probably wasn’t going to sustain the revenue growth rate we needed, and that we needed to make some tough internal trade-offs,” says Jackson
He cites his first official task as VP of Product as an example. “In 2015, we were struggling with the decision of shutting down this product called Carousel, which was a beautiful consumer photo sharing app. It was very popular in some circles and we had a lot of folks working on it, but it wasn’t growing in a way that would have moved the needle for the company. It was a key moment for us internally — could we afford to support and invest in this consumer-oriented part of the company, or did we really need to turn the ship and focus 100% on our SaaS business?” says Jackson.
“We chose the latter, which was in retrospect a good decision. Over 2016 and 2017, we got intensely focused on understanding our entire funnel, from acquisition and activation to retention and expansion. We were able to build an incredibly efficient self-service business. That enabled us to have the revenue predictability that was key to our 2018 IPO.”
To dig into more of the nitty-gritty of how the team pulled this off in just a few years, Jackson shares a helpful tool they leaned on: “We were inspired by the framework articulated by AG Lafley and Roger Martin in Playing to Win. It argues that your strategy isn’t some mystical concept, it’s a simple set of key choices that reinforce each other, across five main areas:
What is your winning aspiration? The purpose of your enterprise, it’s motivating aspiration.
Where will you play? A playing field where you can achieve that aspiration.
How will you win? The way you will win on the chosen playing field.
What capabilities must be in place? The set and configuration of capabilities required to win in the chosen way.
What management systems are required? The systems and measures that enable the capabilities and support the choices.
“We needed to take a hard look at our current business, which was straddling the consumer and enterprise worlds and decide which direction to row in,” he says. “This framework really brought those debates front and center. We had a legacy in consumer photos, but once we landed on our winning aspiration of becoming a multi-billion dollar public SaaS company by designing a more enlightened way of working, we needed to make different choices, specifically around ‘where to play’ and ‘how to win.’”
That meant focusing more exclusively on enterprise use cases around file sharing and content management. “We invested heavily in projects like Smart Sync and Company Dropbox, to enable large teams to store terabytes of company data in Dropbox. This was well beyond the complexity of our consumer offering, so it required a massive engineering investment over the course of several years,” says Jackson. “We also decided to expand into areas that were adjacent to our strengths around organizing documents. The HelloSign acquisition, and recent announcements around Dropbox Spaces and integrations across other SaaS tools came out of that.”
This also required the team to refine and perfect the self-serve go-to-market motion. “Our entire ‘how to win’ playbook revolved around the key insight that our core product and sharing features landed us within companies, but in-product upsell and our sales teams are what enabled us to expand,” says Jackson. “We built product features that made it easy for people to start using the product with their teams, and upgrade their accounts to Dropbox Business. And all of our sales efforts, both inbound and outbound, went towards activating companies where we already saw organic usage.”
In order to enable these choices, as the framework suggests, the leadership team had to focus on building out a set of internal capabilities and management systems. “We organized our EPD teams around key parts of the strategy. For example, we formed a large ‘pillar’ of around 100 people to focus on Smart Sync and Company Dropbox for the large teams use case,” says Jackson. “We also aligned our growth marketing team with EPD, to form a cross-functional group of engineers, marketers, and analysts to find opportunities to upsell our business plans. This group became very good at forecasting their growth from quarter to quarter.”
Define your product strategy and your revenue growth strategy by crisply articulating your key choices — and making sure those choices reinforce each other.
“It’s easy to focus on diving into execution and experimentation when it comes to a new idea or strategy. But there’s a lot of danger in not fully thinking through strategic pivots. I’d suggest doing this work as early as you can. That way by the time you’re considering an IPO, you’ve already built the internal muscles to have all of this running like clockwork,” says Jackson. “This may seem too cumbersome and process heavy when you’re a Series B startup — frankly it felt that way even at Dropbox. But as you get bigger, you’ll need a wide berth to turn the ship. Strategic pivots aren’t easy to pull off in thousand-person companies.”
Lessons like these will be put to good use as Jackson makes the shift from player on the field to coach in the corner. “I spent the past year and a half advising founders and angel investing, as a way of seeing what it’s like to be in a coaching role rather than an operating role,” he says. “After being an investor now — casually, over the last five years, but more over intensely over the last eighteen months — it's clear that you need to make some pretty dramatic mindset shifts.”
Yet even after Jackson picked up some initial learnings and chose to commit to investing full-time, several other branches sprouted on the decision tree. “Should I try to raise my own fund, continue as an angel or join an existing fund? This crossroads took me back to my days as a founder on the fundraising trail. In our seed fundraising process for Cover, we talked to over 50 investors — angels, seed funds and the big Sand Hill Road firms,” he says.
“We met First Round and Josh Kopelman towards the end of that process, so we had developed a good sense of what all the other VCs were like, and immediately felt that First Round was the right firm for us. Their laser focus on seed stood out from other multi-stage funds. Founders discount this sometimes I think — a seed stage firm helps you prepare for and run a true Series A process, instead of a situation where you feel beholden to a single fund.
The strength of the operating team also stood out. They helped us with our marketing, positioning, and our launch, and the community events put us in direct, frequent contact with other founders going through exactly the same journey as us. Finally, they stood out as a group of service-oriented, kind humans. We never felt misaligned when it came to values.”
Fast forwarding to his present-day decision on how to pursue a career as an investor, Jackson knew that he was looking for that alignment, as well as a way to short circuit the learning cycle as a new investor. “At every point in my career, I developed faster and learned more when I had great mentors and teammates at my side. Joining partners who are five to 10 years ahead of me in their investing careers so I can learn from them seemed like an incredible opportunity, and I couldn’t think of a better place to do that than at First Round,” says Jackson.
“One of my favorite sayings from Josh Kopelman is, ‘I’ll always give you my unvarnished opinion, but at the end of the day you’ll always have my unwavering support.’ That’s what felt most helpful to me when I was a founder navigating my relationships with investors, and that’s what I’m most excited to deliver to the scrappy founding teams I’ll be partnering with at First Round.”
Photography by Bonnie Rae Mills.