In This Edition
🖍️ How a childhood curiosity can become your career
📧 Lessons learned from building Gmail
📝 Why it’s important to focus on more than documentation
Jacob Bank is the Founder and CEO of Relay. Founded in 2021, Relay’s mission is to enable teams to work better together by helping them establish and streamline effective workflows.
Jacob was previously a Director of Product Management at Google, where he led the product teams for Gmail, Google Calendar, and several other Google Workspace products. Prior to that, Jacob was the Co-founder and CEO of Timeful (acquired by Google in 2015), a smart calendar that leveraged insights from behavioral psychology and AI to help people spend time on their most important priorities.
He has a BA in Computer Science from Cornell University and was pursuing a PhD in the AI Lab at Stanford before dropping out to found Timeful.
What inspired you to launch your startup?
I’ve spent my entire career working in the collaboration and productivity space. The origin story for Relay begins in Graduate School when I was studying behavioral economics applied to time management — asking questions such as why do we procrastinate, why do we overestimate how available we're going to be and why do we underestimate how long things take? I wanted to build a new kind of collaboration and productivity tool to help people spend time on what's important to them.
I was so excited about this topic that ultimately I dropped out of my Ph.D. program to start Timeful where we built a digital calendar that made it easy to articulate your priorities and allocate time to them — tasks, habits, projects and goals that are important to us in the long-term, but that we don't prioritize in the short-term — such as running three times a week, devoting two hours to write per day or preparing a group presentation by a certain deadline. We built a great product, raised a few rounds of funding and were acquired by Google.
When I joined Google, I served as the Product Lead for Gmail and Google Calendar. I advanced these products to be more robust and help users improve their productivity — looking at how to make it easier to get through your email quickly, respond to the right email, allocate focus time on your calendar or schedule meetings more efficiently.
After a decade of working on email and calendar clients, I had this sad realization that even though these tools had improved, it didn’t mean organizations were more effective. If you used any of these tools poorly with the wrong workflows, it could actually backfire. I wanted to build a tool that makes it easier for people to do their work more effectively with less stress and more peace of mind. With Relay, we set out to build a layer that lives on top of all your tools, helping you to operate effectively with best practices and save your team a bunch of time to get work done.
What sparked your interest in the productivity field?
I have always been an obsessive planner, even back in Elementary School! I was the kid who when we went to the State park, planned what we would do, how we would get there and back, and where we would picnic.
As the years went by, I realized that I'm the kind of person who sometimes likes planning the trip more than actually going on the trip because it's such a fun puzzle to put together, to set up all of the logistics to make sure you're doing all the right things, making the best use of time and having fun. It wasn’t until Grad school that I realized it was the obvious fit for me to focus on this interest in my career.
While in Grad school, I connected with two really interesting professors — Dan Ariely, a well-known behavioral economist and Yoav Shoham, an AI researcher trained in philosophical logic. Even though their fields are quite different, they were collaborating to build a new type of digital calendar that could help people overcome some of the mistakes they make with time management. When I talked to them, it was an exciting collision of my passions — I could bring together what I was studying and my personal interests to build a tool that helps people plan and schedule.
After a decade of working in productivity, what insights have you gathered about people and time management?
The vast majority of people do not put any effort into organizing their tools or creating upfront structures that make them more effective. It’s actually shocking the percentage of users in Gmail who have ever archived or labeled an email! Most people have a never-ending stream of emails. As a power user, it was a sobering moment, but it was also an opportunity.
If we could create a system that makes it really easy to be organized without putting in a bunch of effort, then we’ve made an impact. Our goal is to give the gift of efficiency and productivity to people who don’t have the energy or motivation to do the work themselves.
What is one project you are particularly proud to have accomplished in your career?
I'm very proud of a feature I created for Gmail — the nudge to reply to an email. No matter how organized you are, everyone has forgotten to reply to an email at some time. The feature looks at emails in the past that we thought with a high probability you might have forgotten to get back to someone.
It seemed like a small feature, but the feedback that we received was incredible — users were grateful that we saved them from missing something important in their lives. It showed the power of a simple feature with a very small amount of assistance, it can have a significant impact on helping people get stuff done.
How have you focused on communications at work in the past, and how will the product you're building now impact how we communicate at work in the future?
I’m building the product I wish I had in my prior roles. As a Product Leader, I spent a lot of my personal time and energy developing my organization’s rhythm of internal communications and success metrics. It was important for me to have a pulse on people’s perspectives.
I realized that the higher you are in leadership, the harder it is to know what's happening because you become disconnected from the day-to-day. Most people have very few interactions with the leader of their division. This made me realize the impression you make in that All Hands or AMA is actually really important to the health of the organization.
I created a rhythm where we had two All Hands meetings per month — the first was content-oriented and the second focused on culture and product demos. Quarterly, we hosted strategy jams with AMAs (ask me anything). To make these happen, we created a robust and complex set of processes that required a lot of preparation — the last thing you want to do is go into a strategy jam with a 15-person team and have no idea what they're doing or not have a pulse on how they are feeling — you can completely lose credibility as a leader. Ultimately, my main success metric for an All Hands was how many people felt comfortable sending me an email or chat messages with feedback. The amount of value I would get was huge.
After doing research, I realized there is no tool available to bring all of this together. You really want an organized dashboard that shows all the ways we communicate as an organization and outlines our processes for making it more effective while measuring success. You would want to map out a workflow where before a key meeting, we automatically created a new notes document, found the best time, invited the right group to the meeting, set up a quick chat session with the manager in advance and send out a survey afterward.
We’ve noticed that 50% of the time, these processes live in someone's head and you hope that they never get sick or leave the company. For the other 50% of companies, someone has taken the time to document it, but the process is stale and not completely followed. We want any leader to feel confident that they are applying the right touch points along the way for their communications with employees to be polished and done well. There’s a very fine line between a helpful guide that makes your life easier and a bureaucracy where you feel like you're doing extra work to jump through hoops. We want to be the helpful tool.
What do you think the future of communications at work looks like?
This massive shift to increasing hybrid and remote is going to have a huge impact on the way organizations communicate. There will be an increased focus on asynchronous communication and effective documentation, if you're working across time zones or not in the physical office. It will force us to be more disciplined in how we document which could actually improve efficiency and institutional wisdom.
People are also going to put a lot more effort into their rhythm of up and down communications — I've already talked to a lot of teams who care much more now about how they run their stand-up process, communicate status updates, give leaders face-time with teams, manage review meetings or lead All Hands. All of this will matter more.
These processes have always been important, but they're more important over time — investing in these processes to make them really good in terms of the discipline of the organization and the quality of the content you produce. It will really pay off over time for employee engagement and attrition.
I don't necessarily think this means that Internal Communications needs to have a higher production value, it just needs to be a high-quality candid message from a person with actionable information. I've worked on a lot of teams that send out a weekly newsletter and the more formatted it is, the less it tends to get read because it’s viewed as an advertisement.
I’ve talked to many CEOs who check off all these boxes of hosting All Hands, sending newsletters and recording videos, but nothing is being read or watched. It’s going to be critically important to iterate on your content and your distribution mechanism to make sure that people actually get value out of it. This means having a feedback loop to evaluate impact. Hopefully, our tool can play a role in all of this.
How do you continue learning about your field?
Because my job is to build a product that helps people do this work effectively, every week, I talk to at least 10 people who are very personally focused on this work. There are thought leaders who I deeply respect and have written down how they work.
Shishir Mehrotra, the CEO of Coda, is one of those people. He has written a great series on rituals of high-performing teams that I highly recommend people check out. He has a book coming out and has also been on podcasts sharing this knowledge, includingby .
Is there anything else you’d like to share or ask our community?
Your readers are the experts on Internal Communications. I would greatly welcome any direct outreach to me to help make their work easier. My success metric will be like how many emails I get to “Jacob at try relay dot com.” Send me your cool ideas to make Relay better or internal communications better.
Thank you for reading The Switchboard. ☎️ Every edition is personally curated by me — Julia Levy. Learn more about why I write. Review the Index of past posts.
If you enjoyed this article, consider sharing it, giving a heart below ❤️, commenting or posting on LinkedIn and Twitter.
As a comms pro trying to live a more Cal Newport-ian work life, this post hit home. Very intriguing stuff---great interview!