SHORT PROFILE
Name:  Richard Crowley
Hometown:  Danville, KY
Undergrad:  Washington University in St. Louis, Engineering
Majors:  Computer Science & Computer Engineering
Activities:  Ultimate frisbee, bicycling, STaRS
Internships:  Yahoo
1st Job:  Engineer @ Flickr
2nd Job:  Engineer @ OpenDNS
3rd Job:  Founder @ DevStructure
4th Job:  Operations Engineer @ Square
5th Job:  Head of Operations @ Betable
6th Job:  Director of Operations @ Slack
7th Job:  Director of Service Engineering @ Slack
Current Job:  Operations Architect @ Slack
Linkedin:  linkedin.com/in/richarddcrowley
Personal:  rcrowley.org
Pinboard:  pinboard.in/u:rcrowley
Twitter:  @rcrowley


Richard Crowley began his engineering career in high school, when he maintained the school’s website and helped teachers who were just getting started integrating technology into their classrooms. It was no surprise when he entered the dual degree program at Washington University and earned a Bachelor of Science degree in both computer engineering and computer science.

Through the WashU network, Crowley found himself “lucky” in that he was able to snag an internship at Yahoo, job offer from Google, and a job offer from Flickr all before graduation. When he moved to Silicon Valley, Crowley’s career only propelled forward, with him working for companies like OpenDNS (founded by a fellow WashU alum), Square and Betable. He co-founded DevStructure, a configuration management model that didn’t work as a business but ultimately helped him find define his passion as a leader, not a manager, in software operations.

Crowley currently serves as the operations architect at Slack, the innovative leader in workplace communication and collaboration. Here, Crowley shares how he became acquainted with David Filo, co-founder of Yahoo, Stewart Butterfield and other high-profile tech luminaries, and how to navigate the software engineering job market.

Danville Kentucky downtown
Downtown Danville, KY

Where were you born and raised?

I was born and raised in Danville, Kentucky. I always called it a small town. There are definitely smaller towns, but it is about 15,000 people and about 40 minutes from the closest “big” city, which is Lexington. You had to really mean it to go to even a moderately-sized city. In the town there is a small, thousand-person liberal arts college called Centre College, so there’s an academic community throughout town and especially near my house, because we lived a block from the college.

What was family life like?

I have two younger sisters, and we’re all spaced two years apart. My dad has always been an engineer working with steam systems, the kind of systems in big industrial facilities and giant buildings — not your average water heater. He actually went to business school, but became an engineer. When I was young, my mom was a medical technologist and worked in the lab at the local hospital. Since then, she has converted to working for the Kentucky Department of Education. Education has been an underlying theme in my family for as long as I can remember. Both of my parents served on the local school board in the district where we all went to school.

As a child, did you have a dream job?

Everybody has their unreasonable goal, right? I wanted to be professional golfer for a long time. I played a lot of golf and I was decidedly decent, but nowhere near a real competitive golfer. There was a time where I didn’t really know, but by late middle school or early high school I really got into computers. There was a summer program in Kentucky called the Governor’s Scholars Program. Students who were selected went away for five weeks in the summer between their junior and senior years of high school. We stayed on a college campus with others around the same age, who were theoretically the best and brightest in the state. We picked a major and went to classes, but it was intended to broaden your horizons rather than prepare you for college. I chose engineering and was really, at that point, hooked. I knew that was the kind of work that I wanted to do.

What was the first job you had?

Freshman year of high school I started working with computers for the school district. I was part of a group of a few students who would fix broken machines and reimage them to get fresh software and upgrades to keep the aging fleet of PCs running a little bit longer. It’s a public school district, so you can’t just replace them all the time.

There was one person in that group, a senior at the time and the older brother of a good friend, who had a slightly different job. His job was to run the schools website and support the teachers if they needed help. This was the late ’90s and early 2000s. He was helping teachers who were just getting into using the web to enhance their classroom experiences.

Before work every day, for maybe 20 minutes at a time, he was basically teaching me to program. He and I would work on a little game of Pong for 20 minutes a day. In subsequent years after he graduated, I took over the website and built tools for the teachers to enter grades, schedule buses for field trips and stuff like that. So that was the beginning of my career as web developer.

How did you go from Danville Kentucky to Washington University in St. Louis?

A family vacation to Seattle and later to New York when I was in high school kind of confirmed for me that I liked big cities a lot. When I started putting together college criteria, I knew I wanted to go somewhere larger than the cities I knew, so larger than Lexington, Kentucky, which has about a quarter of a million people living there. I also wanted to be close enough to drive home for holidays.

After visiting places like Georgia Tech and doing a little research on places like Illinois Urbana-Champaign, I developed a belief that I wanted to go someplace that wasn’t a pure engineering school. I looked at some other places like the University of Louisville. This is a terribly full of myself thing to say, but I got a bad taste in my mouth from the schools in Kentucky because they seemed so eager to get me there. It felt like there was a risk that they wouldn’t have enough other students who would really push my limits.

One goal of the Governor’s Scholars Program that I took part in was to get students from Kentucky to stay in Kentucky and to introduce them to others who could push their boundaries. There are definitely many, but what I found after giving WashU a chance was that they had something really special going on. Everybody knows that WashU the largest postal budget in the world, so you get a lot of mail. Eventually you relent and visit. WashU really struck the right balance for me. There was no way I would be anywhere near the smartest person at WashU, and I found that ring true for me every year. I saw that it was a school where people excelled in engineering as well as the hard sciences, social sciences, English and other languages, and everything in between. That really appealed to me.

How did you decide what to study at WashU?

I went in thinking and declaring that I would do computer engineering, which is the hardware design side of the department. It’s somewhere in between computer science, which is theoretical, programming and software oriented, and electrical engineering. I thought that was the sweet spot because it gave me options. I discovered that was a pretty good guess, because I didn’t enjoy, as much, the topics like “How big should this transistor be?” that electrical engineers would argue for days about, as much as I enjoyed what the logic we were designing could do. So I ended up pursuing the dual hardware and software degree.

“I come into the room generally knowing more about how the underlying hardware works then many other folks who I work with professionally is a real advantage”

Looking back, how beneficial was that decision?

I think breadth of understanding is a very valuable thing. The fact that I come into the room generally knowing more about how the underlying hardware works then many other folks who I work with professionally is a real advantage to me. Having the ability to move up and down through the layers of abstraction is really valuable.  

Richard and Katherine Crowley Met at WashU in Hurd Hall
Richard met his future wife, Katherine, in Hurd Hall

When you weren’t building computers or programming, what were you doing at WashU?

I dabbled in a lot of Ultimate Frisbee. I rode bicycles. But I really am a simple and computer-focused guy. I had a work study job that I was assigned by the university, which I quit on my first day. It was basically a data entry job. The people were nice, but I knew there had to be some kind of a programming job out there that was more similar to what I was doing and high school. I eventually found that through the STaRS (Student Technology and Resource Support) program. We pitched our services to departments and built their website and software systems for them. We worked on everything from the off-campus, university-owned housing search and management system to the English department website, Student Union and so on. I put my actual skills to work there and eventually managed a team of people, where I was the one meeting with customers, making estimates and planning the work. I really enjoyed the job very much.

Yahoo logo

When did you start thinking about life after WashU? How did you approach it?

I started thinking about it midway through school outside of just these vague notions like “I like cities” and “I really enjoyed that vacation to Seattle 10 years ago.” Beyond that, I really had open expectations for what would take hold. I left the STaRS program job about halfway through college. My junior year, I took a job with a professor to build hardware. I wanted to put the hardware part of my education to work, and it was really enjoyable. At the time, I really could see myself taking a job with the professor’s company that the university had spun out called Exegy and having had a really good time.

“I got more and more excited about having essentially a cheat code to get into the main event”

And then the WashU network kind of upended that for me. An alum from the business school named Wayne Teeger came by and asked the career center to find interns for Yahoo. I applied and got an internship offer to work on Yahoo’s operations team. I felt like it was an opportunity that I couldn’t pass up. It seemed like an invitation to the main event. I didn’t know much about even the geography of Silicon Valley and how close San Jose and Palo Alto and San Francisco are together, which is a strange thing to think now. As I learned about that, I got more and more excited about having essentially a cheat code to get into the main event, where all the most exciting stuff was happening.

That certainly was an influencing factor in what I think ultimately was a pretty accurate realization that the exciting work happening with hardware was more along the line of “how big should the transistor be?” It was not the design of fundamentally new logic as much as it was how to get the right performance, power, space and manufacturing tolerances right. Like electrical engineering, that wasn’t as exciting to me. I made the decision when I took that internship to point my career in the direction of software rather than hardware.

You got the Yahoo internship from the career center?

Yes, the career center sent out an email letting students know there was a rather last-minute internship opportunity to see if anyone was interested. I put my resume in.

Did you have any other plans for internships?

I had every intention of working that summer for that professor on that hardware project. I feel bad to this day about giving up those plans, but it seemed like — and proved to be — too good of an opportunity to pass up.

How did the Yahoo internship evolve into your job search?

It’s really all about who you know, right? During the Yahoo internship, I was conscious of that reality and tried to use the gift that was given to me by Wayne. And honestly, you have no idea how big of a gift it was. Wayne is a WashU alumnus who has a soft spot and a desire to help WashU students get their first jobs. When I submitted my resume to him I had switched something around on my computer such that the resume I sent to him was horribly formatted. Usually, as a hiring manager, someone who can’t even bother to email you their resume correctly just gets rejected. But Wayne was a kind and patient enough soul that he let me know something had gone wrong and gave me a second shot at giving him my resume. And it worked out. That level of care for the WashU community is something that I remember and try to pay forward myself.

Again, I’m conscious that it’s all about who you know. I met a few people who turned out to be important. I got to know one of the founders of Yahoo, David Filo, and that following school year, after I had convinced them to let me continue my internship as a part-time remote employee — which is the best work study job ever, by the way — I got David Filo to come speak to the technology entrepreneurship class that Professor Patrick Crowley (no relation) was teaching. He talked about the founding of Yahoo, spinning it out from the Stanford Graduate School and the company’s early identity crises about whether it was a media or technology company and how the years beyond that actually went. It was very, very interesting.

Flickr logo

I also met Cal Henderson and Stewart Butterfield, who were two of the leaders of Flickr, which had been acquired by Yahoo a little before I began that internship. I got to know them and really tried to impress them so they would give me a job at Flickr. When I left that internship, I left with a promise of a job at at Yahoo and possibly at Flickr. I really wanted to work there more than any of the other possibilities.

Coming out of that summer, I thought I didn’t need to do job interviews because I already had something going, and that felt really good. At the same time, I really did want to make sure that I was going to end up working at Flickr. A Google recruiter reached out to me and I ended up doing the phone interview and then flying out to Mountain View for the in-person interview. I wanted to see if I could get a job offer from them and measure up at that level. And I did get a job offer from Google.

“Stewart Butterfield called me about 15 minutes later to tell me to calm down because I had a job. My plan worked.”

The very first thing I did was call the Yahoo recruiters and tell them I really wanted to work at Flickr and that I need to know whether I would be working there after graduation. I’m sitting on this exploding Google job offer that I’m tempted to sign unless I can know for sure that I’m working at Flickr. Stewart Butterfield called me about 15 minutes later to tell me to calm down because I had a job at Flickr. My plan worked.

How does the operations intern at Yahoo become friends with the founder of Yahoo?

I think he just liked hanging out with interns. He came to most of the intern social events and would shake hands and get to know people. I think that he liked the youthful spirit, the anything is possible attitude — all those things that interns bring with them. I think that was really something that he valued and probably was a helpful retention tactic to turn those interns into full-time employees.

You chose Flickr, arguably Yahoo, over Google, which would be heretical today.  

Yeah. That was 2006, a time at which Yahoo really seemed like it was going to get itself together. That was before Facebook had clearly won the social wars. That was before Yahoo had sold all of its credibility in search. They were making some really smart strategic acquisitions like Flickr, Del.icio.us and Upcoming that would change the way people interacted online and the overall experience. There was some momentum and some good feeling there. It was genuinely exciting to be a part of it for a little while.

“They asked me questions like what superpower I would prefer to have and then started to poke holes in its functionality.”

You never had to actually interview for your job at Flickr, did you?

I kind of did. I had an interview with Stewart and Cal over the summer, during my internship. That interview was interesting. If I’m looking back on that now with the lens of having done tons and tons of interviews with Slack, it makes sense. They were focused a lot more on how I thought and how I would contribute and work with their team rather than my computer programming chops, because I had already completed a successful internship at Yahoo showing them that I could program. They asked me questions like what superpower I would prefer to have and then started to poke holes in its functionality. I think I said that I would choose teleportation, and then they would ask me what would happen if I teleported inside a refrigerator. What they were trying to tease apart is whether I could improvise or take a left turn and keep right on going. They wanted to make sure I could think critically and evolve my thinking on the spot. For most situations I have come across professionally, that’s the bigger differentiator. It’s not typically one person being a superhuman programmer and another not. It’s about those critical thinking skills and being able to improvise successfully.

It sounds like that’s something that you interview for now when you interview at Slack?

I think so. I think everybody has their own definition of what engineering is. There are people who say an engineer is someone who can do for $1 with any idiot can do for $5, and things like that. I think an engineer’s mindset is one of being very comfortable in managing complexity and that often means being able to selectively put abstractions up in your mind, to assume that things just work, and then a moment later to be able to go deeper with that to question how it works and whether it can be adapted.

Did you do any specific preparation for that interview with Cal and Stewart?

I was pretty dumb when I was in college. I don’t think I realized it was an interview at the time.

Did you do any kind of follow up?

I certainly tried to keep in touch with them. I saw Cal at SXSW that spring and I made a point to say hello and thank him for his time and consideration in the summer when they had talked to me. At that point, I was signed up to work for them, so I really tried to impress upon him that I was thankful for that opportunity and looking forward to starting.

Google logo

How did the Google recruiter find you?

I believe they found me through something like LinkedIn or through events at WashU. Right at the end of my time at WashU the bigger tech companies started to recruit there. For a while it was mostly regional companies recruiting, but by my senior year Google, Microsoft, and Yahoo all were recruiting there as well.

What was the Google interview process like?

Google’s interview process was incredibly technical. I think they’ve changed a lot in the intervening years under Laszlo Bock and the research they’ve done about what makes good employees. I got some of the classic Google brain teasers, like how many golf balls fit into a school bus. They also asked how I would go about sorting some audacious amount of data stored across 10 or 100 servers. Even during the phone interview a recruiter was asking me the running time of various well-known algorithms. It was trivia that one should know, but it also doesn’t make you a bad programmer if you don’t. I had lunch with a Google engineer, which was the most social part of the day. I got to talk a lot more about the projects I had done in college, what I learned from them and how I approached later problems based on what I had learned. If I’m looking back on that as a hiring manager now, that was probably the most valuable portion of that interview.

“The stories of how people learn and adapt are probably the most valuable things, as opposed to how many golf balls I thought might fit in a school bus”

Most valuable for them or you?

For them. I don’t know if they realized it at the time, but I bet they do now. The stories of how people learn and adapt are probably the most valuable things they got out of me that day, as opposed to how many golf balls I thought might fit in a school bus or how to sort data.

What was it like after you did the on site at Mountain View?

After the on-site interview, they were actually relatively quick in turning around a job offer. Most of the back and forth was up front. There were a couple of phone interviews that were very robotic, and then there was the trip to Mountain View. It was basically an overnight trip.

“Naively, I was very happy with it, and so I didn’t push the issue.” 

You had an offer from Google and Flickr, so did you negotiate?

I didn’t. Remember how I said I was an idiot when I was in college? It would have been a great opportunity. Truthfully, I didn’t even know when I was given an offer at the end of my internship whether there was an opportunity to negotiate that, and I didn’t. Naively, I was very happy with it, and so I didn’t push the issue. I did negotiate when I was about to join OpenDNS and felt like I had done right by myself. If you get to a place where the company feels like they’re getting a good deal and the employee feels like they’re getting a good deal, that’s a happy place to be. It can be very adversarial for someone to extract maximum monthly dollar value from the company and then have to work with those people all day every day.

When do you think students should or should not negotiate?

I think when you’re coming out of an internship program and lots of people are getting job offers together, there is a fairness argument for the company to do very little negotiation on those offers. There’s such a wide disparity in negotiating skill and even awareness that one should with a huge crop of new college graduates coming out of internships. I definitely don’t think it’s appropriate to negotiate the internship offer itself. It’s debatable whether one should negotiate their first job offer after coming out of an internship. I think if everyone could agree to do it and be good at it all at the same time, I think everyone should try to negotiate. The fairness argument, again, having been on the other side of that — holds a lot of weight with me.

Richard Crowley Exploring San Francisco
Richard found the ‘cheat code’ to the main event in San Francisco

How did you prepare for life in the working world?

To continue the series of stories about me being stupid… I received a small signing bonus from Yahoo, which I think was a very standard offer from them at the time. I used that to do things like buy a couch, a bed and a TV, some knives, a couple of pans and those kinds of things. I realized much later that their intention for that was actually for me to pay for a short-term, readily available living situation.

I moved out to California and I had it all lined up. I had a flight. I would fly red eye and first thing in the morning I would take a cab to straight to an open house for an apartment. I had four appointments lined up and I thought I would get one of them. I had a contingency plan in case I didn’t. I had an intern friend to stay with. I did end up getting the second or third of those apartments, though it wasn’t ready yet. I had to find a place to stay for a couple of weeks, and that was an incredibly stressful thing. I had no money. I had no paycheck coming my way and I was living out of a suitcase with a few different friends so I wouldn’t annoy them too much in any single stretch.

If I were doing that again or if I were ever moving to another city again, having a pretty decent sized slush fund with a few weeks living expenses would be a good idea. Having a couple of weeks before starting work to get things like a parking permit or signing a lease without stressing about missing orientation at work is necessary. Spacing that out a little better would have been very smart of me. I would very much encourage anyone who is moving cities not to rush like I did.

“It was a missed opportunity to learn about really big companies”

Anything you wish you would have done before you started your first real job?

This is pretty specific to that opportunity, but I wish that I had taken more advantage of the fact that Flickr was owned by Yahoo at the time. What I mean is this: when I say I worked at Flickr, the name that I’m using is not an accident. I worked at Flickr. I did not work at Yahoo. I didn’t pay attention to Yahoo. I did not understand the organizational structure of Yahoo. I did not understand the politics of Yahoo. I did not understand their career path at Yahoo. I worked at Flickr. That would have been fine for a while, but it was a missed opportunity for me to learn about really big companies. I could have learned about the kinds of jobs that exist and the way people work together. Not taking the opportunity meant that I have had to learn that day by day as Slack has grown. Slack employs about 1,000 people now, and every little inflection point in the number of employees is something new that I need to learn that I could have learned just by paying attention at Yahoo.

OpenDNS Logo

How did you know it was time to leave Flickr?

So here’s another WashU connection that comes together. When I was graduating from WashU, my boss in that STaRS program told me that I should look up David Ulevitch when I got to California. He is the founder and CEO of OpenDNS. I got in touch with David, met him, and ended up taking a job offer from OpenDNS. I left Flickr and went to OpenDNS because they offered me a really exciting project to work on. At Flickr I was working on the cross-platform Windows and Mac upload software. I was very proud of what I’ve had built, but was very frustrated that I spent a lot of my time debugging Windows software. The offer to go work at OpenDNS on something that was entirely run on servers under our control and that I would get to design and build and debug and own myself was really exciting.

I spent a couple years at OpenDNS, which was a DNS stats system that told you a little bit about what kind of traffic you were sending to OpenDNS as a user and would count for entire networks. It logged how many times users went to different domains, where in the world they were, and a whole bunch of other interesting charts and graphs. When OpenDNS first launched, it was processing about eight billion queries per day. By the end it was processing about 24 billion queries per day.

I got to speak in 2009 at Velocity, which was the first professional public speaking engagement for which I applied and was accepted to speak. It was really exciting to tell people what we built and why we had done it the way we had, in a way defending that design and software out in public was really rewarding and something that I continue to do as often as I can.

Richard Crowley Can Code and Dance
Richard, the renaissance man, can code and dance

How did you learn about what you loved vs. liked to do and use that to determine what to do next?

When I was at OpenDNS, it was the first time that I had been given pretty much free reign over a pretty large cluster of computers that I was trying to point all the same direction to accomplish tasks together. I developed an almost obsessive compulsive fascination with the way that they were configured, the way that it was automated and the way that I confirmed that it was working and still up to date. That led me into a whole genre of software called configuration management and learning about tools like Puppet and Chef, for those who are paying attention to the software details. That ultimately led me to leave OpenDNS to start a company with Matt Tanase called DevStructure. The goal was to make a configuration management tool that worked very differently than other similar products on the market. The opportunity at OpenDNS to discover which part of the software that I obsessed over was really valuable to me.

“If you work at Yahoo or Google you can do nothing but work with browsers, but if you work at OpenDNS when it’s 11 people, you have to write the software that runs in a browser and all the stuff underneath of it.”

Did you create that opportunity or was it given to you?

I think it was a combination of things. We were a very small group at the time. There were 11 employees when I joined, so there was not an operations team that would hand me ready-to-go servers. There were no rules to say you have to use this particular kind of software or architecture. Those decisions were left to me because there was no one else with time to make them. I was given a really wide purview there, from how the computers themselves are configured to how the software that’s running on them works, to the interface that it exposes to customers. I got enough experience with the entire spectrum of specializations that I could see which ones I liked and which ones I didn’t. I feel like that’s an almost unavoidable aspect of working for a very small company. You’re going to have to do several jobs. If you work at Yahoo or Google you can do nothing but work with browsers, but if you work at OpenDNS when it’s 11 people, you have to write the software that runs in a browser and all the stuff underneath of it.

“Will I have a job at dinner?”

What are the tradeoff of working in a small versus large company?

The classic trade-off in working for a very small company is the uncertainty about outcome. I don’t even mean wondering how much the company will sell for, because the reality is most of them won’t. The downside uncertainty is what’s more preoccupying: The “Will I have a job at dinner?” worry that exists to some degree with any tiny company. It was a very minor version of that at OpenDNS. They had very good leadership and very good marketing to help them get to the point when I joined where I think the risk of outright failure was very low.

I think it’s healthy to understand, and perhaps you have to live it to understand, but it’s healthy to understand how you cope with that as an employee. If you’re comfortable with that kind of uncertainty, there are a lot of upsides to working for those small companies. You get to do many jobs. You get to change jobs, so to speak, pretty regularly as the needs of the company change. New people are hired who can take over part of what you were doing. All of those things are interesting challenges and you definitely get them at a small company. You only maybe get them at a big company.

Square logo

You, like most CS graduates, have recruiters chasing them. How do you think students should navigate that?

First and foremost, they should respond respectfully and graciously. The practice of being mean to recruiters is not really an acceptable personality trait to me. I don’t respond to all their emails, but when I do, it’s thanks, but no thanks, rather than “Why are you wasting my time?” or some indignant response. When you’re lucky enough to have recruiters reaching out to you and you’re thinking about whether and how to respond, I think learning opportunities is a really good rubric to use.

“…it’s really tough to argue — if you look at how Square has evolved — that those decisions were wrong. They were just wrong for me.”

If you’re at all considering what comes next for you in your career, understanding what you could stand to learn more about to broaden your skills is beneficial. You can be on the lookout for opportunities that will help provide those skills. You may also look at different sizes of companies and in different industries to help solidify what you value and why. For instance, after we decided DevStructure was not a business, it was an open source project at best, I took a job at Square, which was a consulting client that I had for a long time. I ended up leaving relatively quickly because the culture of the company wasn’t what I wanted to work in. It was very product and polish driven instead of engineering driven. We would make decisions that I wouldn’t have made and didn’t agree with, and yet it’s really tough to argue — if you look at how Square has evolved — that those decisions were wrong. They were just wrong for me.

Then I ended up working for a couple of years with friends on the very audacious idea for a company called Betable, an API for licensed regulated gambling in Europe. That was an opportunity to build everything absolutely from scratch and make all of my own mistakes and fix them. What that solidified for me was that same feeling that I started to get at OpenDNS.

At that point I had worked in photo sharing, internet infrastructure and payments, gambling, a developer-focused company, and across the board, I found that I was most interested in the plumbing, or the stuff that was common among all those companies. That was a strong signal to me as to what kinds of work, what companies and what departments within companies I should be seeking out. I started to more aggressively focus on job titles like operations engineering, systems engineering and site reliability engineering, or for signals that you’re working in the lower layers in support of whatever the product happens to be.

“Leading by influence, asking questions and a deep, shared understanding of what you’re building is much more satisfying to me than any kind of command and control management,”

The other learning opportunity I feel like you can seek out when you are considering what opportunities to explore further is the company size aspect. There are folks who perform well at 10 person companies and start to flounder at 100 or 1,000 person companies. Yet there are also opportunities to learn more about how you work and what you value in those larger places. I had only ever worked for tiny companies and as Slack has grown up I’ve discovered something that I really should have learned at Yahoo, which is just how much of a difference there is between management and leadership. When you are out of small company, management and leadership tend, for some good and some bad reasons, to be pretty conflated. I went into management at Slack and stayed there for three and a half years. By the end of that time, when I gave up my management responsibilities to someone else I had hired and trained for leadership responsibilities — that was a very freeing thing. Leading by influence, asking questions and a deep, shared understanding of what you’re building is much more satisfying to me than any kind of command and control management, as well as all of the career support functionality of a manager. That just was not the kind of work that I felt best suited or most interested in doing. I could only really learn that distinction at a slightly larger company. 

That form of flattery… the way that I phrased it jokingly, but not really joking, is “I think I could always have a job by dinner time.” That’s an enormous insurance policy. That’s the most emboldening thing. If you know that you have options, you can throw the Hail Mary. You can try to find something that is outside your comfort zone that is a big risk knowing that if it fails that you have options. Not everybody is wired to seek that out and not everybody wants to. It’s not a black mark if one doesn’t choose that, but I feel like most WashU students have some amount of that ambition, so they’re going to seek that out. Having options, though, that’s license to seek harder and take bigger risks, not a license to be lazy.

What do you think students should do to figure out what they want to do or don’t want to while they are in school?

Thinking all the way back to why I ended up choosing to go to WashU, the breadth of experience that you can acquire there is easier to get in college than it is to get anywhere else. I think, more than anything, I would encourage people to be a math major who took some film studies classes, or be an English major who’s got a minor in economics or even just took one class. I took maybe three economic classes because I lived with a bunch of economists. Two of them have a Ph.D. in economics now and I just needed to be able to argue with them better. That turned out to be a really valuable base of knowledge to have.

Richard Crowley and The Slack Ops Team
The Slack Ops team

What do you wish someone would have told you during your job search?

I’ve had a very fortunate run of people I have met, offers that I have been given and opportunities that I have lucked into. Stewart, the CEO of Slack’s best advice to entrepreneurs is “Be Lucky.” You can read all of the playfulness you want into that, but also, whichever physicist or mathematician claimed that luck is when opportunity meets preparation was onto something. I think I got lucky enough that I don’t feel like there’s a glaring “if only I had known” fact out there, and I feel very fortunate about that.

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What preparation did you do to ensure you were lucky?

I think early in one’s career, it’s important to recognize that the job you take out of college or even the job after that is highly unlikely to be your job for the rest of your career like it was for many of our parents and certainly for our grandparents. Of course, you can take that too far. I actually received feedback in an interview once that a company was going to make me an offer, but they were concerned that I was just going to leave really quickly because I had jumped around a lot. At that time my average tenure had been about two years, which, compared to some people is actually kind of a long time in San Francisco.

I think there’s value early in your career in being willing to move around to get those experiences with the express goal of finding out what is going to keep you engaged longer. I’ve been at Slack for almost four years now and have no intention of going anywhere. If I ever leave, the next place I work might be for 10, 12 or 15 years, because I’m getting better at finding what excites me. Being okay with moving around a bit early in your career is a good strategy to help find where you’re really going to be most engaged, most productive and contribute the most.

Did you have any mentors along the way, and how did you find them?

I considered Corey Maul, who was my boss in that STaRS program and David Ulevitch to both be strong mentors for me during certain periods. In both of those cases, I think the opportunity was situational and the decision to ask for more feedback to try to get them to push me harder was taking advantage of the opportunity there. I know people professionally who have sought out specific people at different companies as mentors to try to emulate that person’s path. I think there’s a lot of value in that. Having come around and worked for Cal Henderson a second time, there’s a similar kind of mentorship that he provides in that I’m trying to get him to push me to be my best.

“There’s no such thing as being totally on top of all the work.”

Is there any other wisdom you want to share with students?

Two things come to mind. One is: It’s really a bummer to hear people say college was the best years of their lives. If you’re thoughtful about it, the years after college can be very much the same level of stimulation, but you’re getting paid for it. The other thing I would offer is that there’s absolutely no such thing as being caught up. There’s no such thing as being totally on top of all the work. You will never be able to work late one night and suddenly everything is great, so pace yourself and recognize that there will always be more to do. The marathon is the game we’re playing.

Richard Crowley With His Family
Richard, Katherine, and their daughter live in San Francisco, CA

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