07 Feb Smooth Scaling: 3 Female Tech CEOs. Lessons on How to Scale Faster, Better & Farther – SaaStr
Have you ever wondered what it’s like to be the captain of the ship, steering a startup to breaking through $10, 20, 40 million ARR—and beyond? In this session, hear from 3 female CEOs who each sit at the helm of a fast-growing Silicon Valley tech company: Accompany, PagerDuty and Usermind. They’ll recount pivotal experiences from their leadership journeys and share key learnings gained from navigating the often choppy (but thrilling) seas of startup scaling.
Announcer: Please welcome Jennifer Tejada, CEO of PagerDuty, Michel Feaster, CEO of Usermind, and Amy Chang, founder of Accompany.
Jennifer Tejada: All right, good morning?
Audience: Good morning.
Jennifer: Wow, are you guys alive? Good morning.
Audience: Good morning.
Jennifer: Oh, much better. What a good looking crowd here at SaaStr. Welcome. Thank you for joining us. It’s the first time I’ve had a sitting room only audience. This is awesome. I hope you guys are comfortable.
As mentioned, I’m Jennifer Tejada. I am very fortunate to be the CEO of PagerDuty. PagerDuty is a late‑stage startup backed by Andreessen Horowitz, Bessemer, and Excel partners. We’re about 400 people based here in San Francisco as well as in Toronto, London, Sydney, and a few other various places around the world.
We are a digital operations management platform. We started it about eight, nine years ago as a learning and notification solution for the DevOps community and are fast becoming the platform for action for digital enterprises as consumers drag us into a truly real‑time world.
I am really excited today to be joined by two wonderful guests. We were talking on the way in. We think we have 30 percent of all female enterprise SaaS CEOs in the world right here.
Jennifer: I’m hoping that there’s more in the audience soon. I’m going to let Amy and Michel both introduce themselves. Welcome, ladies.
Amy Chang: Thanks. Amy Chang, CEO and founder of Accompany. We are basically enterprise‑grade LinkedIn. Think of the data platform that they shut off with their API a few years back. We’ve got that for the enterprise use case, so prospecting, relationship management, all that.
About six months ago, it became self‑automated and self‑learning. That was the exciting part. My formative years were spent at Google, running and growing Google Analytics. We grew it from about 1 percent to about 70 percent of the web, which was a really fun scale‑up, and before that eBay and McKinsey. I’m an electrical engineer by training.
I also serve on the boards of Proctor and Gamble and Cisco. If we have questions on boards, we can talk about that.
Jennifer: [ironically] Not very smart.
Michel Feaster: How do I get to be on that board?
Amy: Well, we could talk about that.
Michel: [laughs] One of these days. Hi Guys. I’m Michel Feaster. Founder and CEO of Usermind. We’re a modern integration platform to transform customer experience. Our investors are Andreessen. That’s how Jen and I know each other.
We’ve raised almost $50 million about 50 people and we’re getting ready for our growth scale.
My life story, I’m a product nerd. That’s what I have been doing, enterprise software for 20 years. My passion is interviewing customers and building software to help them, really passionate about that.
I spent my time in all enterprise software companies. I was at a company called Mercury Interactive for almost a decade. I led the Opsware acquisition, which is how I know all the Andreessen guys.
Then my last startup was a company called Apptio. I was really blessed to be there from employee 16 to about 600, and then I left to found my own company. Super excited to be here with you guys today.
Jennifer: Between the three of us, I think we’ve seen every asset class, we’ve screwed up just about every function that you can and learned from it.
Jennifer: One of the things I love about SaaStr and the reason I’ve been super supportive of this platform is it’s a great opportunity for all of us to not have to learn everything the hard way.
We hope that today we can spend a little time talking about some of the lessons that we’ve learned as leaderships at different levels of scale in a business, from zero to public, and in my case public to private. We’ve seen every investment cycle as well. We basically decided this was just…be a fun way to get together and have a good time.
Jennifer: Hopefully you’ll enjoy it too. First, I’d like to talk a little bit about how leadership has to change as you scale. In my case, this the second time I’ve been a CEO. Before that I was a COO. When I joined PagerDuty we were about 150, 160 people 18 months ago. We’re close to 400 now.
It’s a very different company almost every six months as you’re scaling. I used to know everybody’s name and know what their job was. Now I’m doing security badge checks at the front door of offices to see if people are coming in to steal the laptops.
Jennifer: What you also learn is your leadership style even sometimes has to change to accommodate the size of the organization. Big decisions, important communication, can get done in a room, in a huddle one day. The next day you’re trying to figure out what time to host town hall so that everybody’s awake when it happens as you go through global expansion.
One of the things that is challenging as you’re building out a leadership team is figuring out what decisions do you have to be really involved in and which decisions you delegate? How much guidance do you need to provide? What are you doing versus what are you leading?
If each of you would talk about your journey there, that’d be awesome.
Michel: Sure. Yeah, so I tell all of my team, growth is like rings of a tree. You have to be really conscious when you’re passing through to a new ring of the tree. One of the big things I’ve had to focus on is, when I founded the company, even up to 20 people, I made every decision in the company.
Every product feature, every customer meeting. I had all the contacts. One of the questions I ask myself now is, who has the most information to make the decision? If my CRO is in all the deals and knows all the deals, then he needs to be empowered to make all of the decisions about those deals.
That’s changing dramatically. We’re actually at the point now where even my leadership team is now needing to delegate a significant set of our decisions to the next level managers and directors, which is an interesting thing to see us go through.
The other thing I would say is, I always have one or two things ‑‑ I don’t know about you both ‑‑ that I’m micro‑ing in the company. I’m explicit with my team that these are things that I’m either concerned about or very focused on. Right now, in the company, we’re starting a SWAT team to attack a vertical.
I’ve been very explicit with everybody. I’m leading that SWAT team. I’m personally going to drive that topic. When I do decide to go deep, I try to be really clear with the company so no one’s confused that these are things I feel we have to solve, and own, and drive personally.
Amy: To that end, there’s a concept that has been insanely helpful for me. It’s the concept of commander’s intent. Once you move from the number of people in the room being able to talk to each other, to 40, 100, etc, everybody has to be crystal clear on, what’s the intent for this next two‑week period, this next four‑week period?
What hill are we taking together? Once you get out onto the battlefield, everything…conditions change, minute by minute or day by day. You want people to know, OK, that’s the hill we’re taking. Now the decisions I’m making, how do they get us there or not get us there?
They are able to have the autonomy and the agency to make those decisions on a daily basis when you can’t be there to answer questions. You shouldn’t be there to answer every question for every meeting. That concept, I find, has been extremely helpful.
The other thing that’s been interesting to me, being a product person myself, the person who is running the function in your company that you know best, whether you’re an engineer, or a product person, or a sales person.
When somebody else has to step in and start making those macro decisions because you, as CEO…I have to go close seven‑figure deals now. That’s my job for the company for the next two months, is to close enterprise sales. I’ve got to step back and I have to let her step forward.
That’s been a huge challenge for me, from an identity standpoint, from a, “Oh, I don’t want to step on her toes.” Certain things are opinion. They’re not fact and it’s unclear how they’re going to turn out. If you make a decision one way versus the other.
Letting her have that space to make her decisions and to do it her way has been a challenge for me, but has been fantastic for both of us.
Jennifer: The good news is, as a CEO or a founder, there are no shortage of things that you can’t delegate. There’s no shortage of stuff to do. Every time you think you have everything under control, something blows up in your face. That’s just the nature of the beast.
One of the things that I don’t believe I can delegate as a leader is culture. Culture is not the job of HR or people talent and vibe. Culture starts at the top, just like the fish stinks from the head.
Jennifer: Just remember that. Get promoted or fired. That’s the exit for the CEO. Nowhere to get promoted, so I guess it’s fired. It’s really important that you demand from the top what kind of culture you expect. I’ve said this many times in public before.
Culture is defined by the lowest level of behavior you’re willing to accept.
Not the highest standard that you set by the organization. If you delegate culture to your team as opposed to delegate the expectation and managing those expectations, you aren’t going to get where you need to go as quickly and the cracks will start to show.
Are there other areas where you really feel like your stage in a startup, you just absolutely can’t delegate?
Amy: The hiring decisions and the culture are interrelated. You may not be able to interview every hire. Being very clear on what you will hire and fire for. The culture being clear enough to where there’s some grit to it. It’s not all rainbows and unicorns. It should repel the wrong people and attract the right people.
Reed Hastings’ whole 100‑page pack that he published eight years ago still holds very, very true. Where it’s got to be defined and crisp enough to where…our number one value, and apologies for the cursing, is no assholes.
Even if you’re really, really smart we don’t want to work with assholes. We just don’t.
Jennifer: Who does? Raise your hand if you want to work with assholes. Oh, no body.
Amy: There’s compromises, right?
Amy: Someone’s crazy smart, you’re tempted. You’re like, “Oh, maybe. Maybe it’ll work out.”
Jennifer: What about fundraising? You just raised a round. Can you delegate fundraising?
Michel: No, you can’t delegate fundraising. Actually, this is the first round I even included other people from my team. I’ve historically done all my rounds solo because I wanted to control the relationship, control the information, and kind of own the narrative for the company. It was an interesting thing for me.
The thing I’m really passionate about is the financial plan of the company. We have a lot of discussion on my leadership team about do we want to approve incremental heads in engineering or to product? We just opened in Europe. How many people are we putting there.
I mean, I feel really, really passionately that I don’t delegate the trade offs plan because when you look at burn and top line revenue, it’s basically the life of your company. The number one thing we have to manage or at least that I feel strongly that I have to manage is, how long do we have before we raise the next round.
I think it’s a thing that I didn’t do passionately enough when I raised my first round. I feel like I didn’t know how important being just rigorous and clear about that was. I’m learning the hard way.
We debate it and I take input, but no one can approve a changed plan without me being involved. I feel really strongly about that.
Jennifer: As you grow you start thinking about capital management a little differently. You think about, how long do we have before we have control over destiny and we don’t need cash from others? We can run on our own fuel. Run on our own steam.
I think that’s a really important discussion for leadership teams to have. What’s your philosophy on how much capital you think you need? What the balance is between growth and profitability. Some of you may be bootstrapped and thinking about, what do we need to drive expansion?
How fast can we grow? These are really important questions.
One of the things that I’ve experienced as a repeat CEO is as soon as you think you know everything you need to know you screw it up. You have to constantly be open to learning and apply this kind of ‘learn it all mindset’ as opposed to a ‘know it all mindset’.
In our case, most of our employees, I think almost all of our employees, are a lot younger than I am. They’re teaching me new things every day. I have not done the job of my target customer. I’m learning a lot about that persona and what that means. We’re inventing a new SaaS revenue motion. We have kind of a unique business in that regard. It doesn’t look like any other enterprise software companies.
In some cases I’ve had to help my leadership team unlearn things that they know, wisdom that they bring to the table. What have you had to help your leadership team learn as you’ve grown as you scale?
Amy: My co‑founder at STO has this great saying. He’s like, “The whole point is when you wake up on Monday morning you will have no idea what the frick you will have had to learn by Friday.” That is the most exciting thing because every single week there is something that you will not have known how to do, right? That’s kind of the point. There’s all kinds of stuff.
A lot of us are Google people. We’re more consumer side. All of the enterprise pieces, we are learning as we go. We’re lucky because the Cisco folks have been very helpful and your folks have been very helpful.
Yeah, every single Monday we wake up and we kind of go, “OK. This week this is what we need to know. Now, we’re going to go get that knowledge, whether we’re going to read it, experiment it, do it, or we’re going to talk to people who’ve already done it two, three times before. We’re going to grab time with them and we’re going to get it done.
Jennifer: Talk about exemplifying a growth mindset, I met Amy and like 11 minutes later she said, “Can I bring my team to your office and spy on your sales people all day long?”
Amy: She said yes.
Jennifer: In market research, who’s going to say no to that? Like, “OK.” Some of the sales people that helped Amy out are here today.
I recently called Michel for some advice for something very product specific because she is a bonafide product. She considers herself a nerd expert, right?
Jennifer: Yeah, I’ve run product before, but I don’t know everything there is to know. A big help for me as a leader has been seeing other people not be afraid to ask me for help. It enables me to feel confident in asking other people for help.
When you get asked for help, who really says no to that? You want to be helpful generally, right?
Michel: Yeah. One of the most interesting dynamics on my team, and founders in the room will probably have this, is I have some members of my direct team who’ve done their roles before. My CRO took a company to 80 million. My CFO has had multiple exits and been a serial CFO in the Seattle area.
Then I have the majority of my team is in their role for the first time. I call them ascenders. My head of engineering teams has never been at the exec table before. I find that I have to help them really differently.
I have to help a lot of the people who are in their seats for the first time really make sure that they get that they’re empowered at that table. We need them to lean in, bring their voice, and engage in constructive conflict.
Then when I look at my serial people one of the challenge I give to them is this isn’t the business you built before. My CFO, for example, hasn’t really done SaaS before. I’ve gotten them mentors to help them.
For me, the most important thing is that the team is stronger than any one individual. My most important outcome at that table is like, “How do I create a perfect team?” That whole “Remember the Titans” thing, of we have to be perfect as a team.
Amy: Including you, right?
Michel: Yeah, well they all just pick me up.
Amy: The hero complex is a thing.
Michel: I’ve made every mistake in the world. I feel like literally every. The history of our company is like every mistake that I made. Pick up a rock and there’s a Michel turd underneath there.
Jennifer: We often say you’ve got to burn the first few pancakes before you get them perfectly golden brown, right?
Michel: Yeah. No, but that dynamic was a real learning experience for me in being a first time CEO. Managing them differently. Really getting them different kinds of coaches. They need different help.
Michel: They think about the company differently. Some of them have done organizational planning and development before. Some haven’t. Some have done calibration. Some haven’t.
Even just norming in my own team our expectation of ourselves has been a journey and really eye opening since I was part of an executive team, but I was kind of participating versus leading and driving that key development.
Jennifer: How do you strike the balance between driving your team hard, really stretching them, pushing them, making sure that they’re not constrained by their ability to imagine a future and keeping the encouraged, engaged, and celebrating enough success?
There are witnesses here.
Jennifer: I could be accused of moving on very quickly, like success celebration is 40 seconds and then we’re onto what we need to fix and do better the next time. How do you strike that balance, Amy?
Amy: Oh, I got that feedback probably eight years ago. I got my first coach while I was at Google. They got one for me because I needed one. I was driving the team too hard. We were not celebrating those moments enough. It was too much. There was strong feedback.
You need to acknowledge when someone does something right. Be specific about praise that you give and remember to give it. Give it literally in order of magnitude more than you think it’s necessary. I have worked on that for the last 10 years.
I think I’ve gotten better. I mean my team will have to put the proof in the pudding.
Jennifer: Anybody here to let us know?
Jennifer: Any Accompany people?
Amy: No. They’re all working.
Jennifer: We’ll check that later.
Amy: We do do that. Now we try to give specific praise. We actually have programs inside of the company. There’s peer bonuses that people can give. They can give each other, “M’s” and gift certificates for something someone did that’s great.
We want the team to be acknowledging each other and the team to be thanking each other. We’re trying to create a culture where people appreciate one another and say thank you whenever someone goes the extra mile. We’re trying to do that.
I’m trying to just make it a thing for me on every Sunday. To think about who I need to appreciate for this week and what emails do I need to send. I want to be specific when I send them and thank them really for the thing that was above and beyond that week. I’m trying to remember to do it every single week.
Jennifer: That’s a great idea. Instead of cleaning out your inbox on Sunday thinking about who need to appreciate, I’m going to…I might try that. Get ready guys. Monday.
Jennifer: Good news from Jen on Monday. Michel, how about you? How do you manage to strike that down?
Michel: Oh my gosh, I suck at that.
Michel: I suck at that.
Jennifer: Honesty, right there.
Michel: That’s the answer to that question. I suck at that. In the company, we have…I often take a wait class in the company. Meaning my directs are different than…I see in the company who’s an engineer who just worked over the weekend.
I probably spend a lot more trying to publicly praise the rest of the company. More than my directs. When people really go above and beyond for the company, that’s what you want to model. That’s an area I make an effort, far more than to the people who work and report to me.
We created a Boom channel on Slack, so I’m famous for walking around saying, “Boom.” The team is called Boomees. A great deal is a sonic boom. So, you guys don’t steal this.
In a team of 50 people, we get five or seven of those a day, and we use those to make awards. You boom someone and you refer to a company value and then we give awards every couple of months, and we actually do that by booms. We count them as opposed to the execs deciding.
With my team, one thing that’s worked for me is I do dinners maybe quarterly or every six months if I want to work on something with them. That’s when I really try to let them know, “This is something I really appreciate about you, that’s great about you.”
For the most part, my expectation is that my directs are…It’s a different discussion. I need them to be motivated but I want to spend 99 percent of the time talking about the business. I would say I definitely do want to acknowledge my team. Everyone’s different. I call my leadership the land of the misfit toys.
One conscious decision you need to make is are you hiring the same people to speed decision‑making, or are you hiring really different people to create conflict? It’s actually harder to create a high‑performing team when people are different. I’m in that category that’s a really strong part of leadership philosophy.
Jennifer: Do you have a good mix of stables and volatiles?
Michel: I do. I have a pretty interesting mix of people.
Jennifer: You’re the volatile?
Michel: I’m a volatile.
Michel: Can I say that I’m volatile as ****.
Michel: I’m definitely a volatile personality.
Jennifer: It’s late‑night TV, right? We can swear?
Michel: Top ten list.
Jennifer: PagerDuty, we have these jars in the offices where you have to put money in if you use an acronym. You can swear as much as you want.
Jennifer: But you cannot use any acronyms because it slows down learning.
Michel: I love that. I want to steal that.
Jennifer: Everybody should have an acronym jar. Swear like sailors. No problem. Like I said, the fish stinks from the head.
Jennifer: Let’s talk a little bit about boards. We’re all at different stages in our business. We’re building boards. I’m adding an appendex. We’ve got investors on our boards. How do you think an approach building and managing a board?
What’s the role of the board in your company? What have you learned from your board? What are you trying to teach your board?
Amy: On the board front, one of the things that I’d like to use the board for is to see around corners. I don’t have time to go to every industry conference, to go be meeting with everyone who’s doing something interesting in that industry.
But they more likely do because they’re interested in the industry or in adjacencies to it.
Sometimes I will ask them, “Hey, will you go to this? Will you meet with this person? Will you try and see what’s going on there?” It’s better leverage for me and they have the context to go do it. Them seeing around corners for me is a fantastic service they provide to me.
The other thing, the service I provide to them then, is no surprises. If there is something controversial that’s going to come up at the next board meeting, I don’t like to blindside them with it.
Chuck Robbins, CEO of Cisco, for example, does this beautifully. He will do pre calls if there’s anything that’s going to be surprising. He will take the time ‑‑ and he’s freaking busy ‑‑ but he will take the time to call every single one of us and let us know that something is up and get our thoughts on it.
When we walk into that room, we’re not blindsided, and we’ve already had time to process and come up with a point of view. I think that’s important. If you’re going to have that level of trust with your board…You’re going to be with these people for 7, 8, 9, 10, given how long companies stay private these days.
Jennifer: Choose them wisely. It’s a long time.
Amy: Choose them very wisely. But invest in that relationship too, because it’s a relationship. When we’re talking about stuff to delegate, that’s one not to delegate. Your board relationships.
You may want other executives on your team to have a relationship with that board member. They need exposure to board members as well, the other portions of your leadership team, but you don’t want to delegate the core relationship because you want that trust to be there.
If shit hits the fan and you need them, you want them to be there with you and to understand the context and how you got there together. I’m a big fan of surprises at the board level and making sure you, this is a silly word, but pre‑syndicate. Give them time to respond and formulate a response.
Michel: I love my board. My first board member was Ben Horowitz and I’ve known him for 10 years. I got a lot of advice. People told me, “Get your biggest shareholder to be someone where you have a lot of loyalty and trust.” That’s been vital. I would do it over again if I could.
If you have a guy like Ben on your board…Actually, I’ve been really thoughtful about follow‑on board member from other VCs, because you need someone really self‑assured, really experienced, in order for them to voice their opinion at that table and be an effective board member.
A big factor for me in adding a board member is the chemistry. Like, do I think that person’s going to add another point of view and actually be willing to throw down in a meeting with Ben or Matt?
I will say I actually get more value from my board outside the board meetings than inside the board meetings. I don’t know if it’s just me or if it’s every CEO. I use them for a lot of things.
I feel like my informal conversations with my board about everything, management challenges I’m having, I’m thinking about hiring a role, I’m thinking about the org structure of the company over the next year, what should I be thinking about, when to open a region, go to market problems, partnerships.
To me, a lot of these conversations where I get so much value don’t happen in the board context. They’re much more one‑on‑ones. I actually, regularly, maybe not in a scheduled fashion, but I spend a lot of time leveraging them to help me think through thorny problems in the company.
The other thing is, I don’t know about you guys, but I’m constantly bumping into a problem I’ve never thought about before. Year from now, I’m going to have to hire my first CMO. I don’t even know what a CMO is and I don’t know really know what they do, how do you do what a good CMO is.
By the way, how is it different from enterprise to…I’m exaggerating, because I work with great CMOs. I’ve never had to really think through that problem. Another way I use my board members is for intros.
I will have them intro me to the two best CMO they know. Each of them, have a coffee or something, and I am doing that a year ahead of knowing I need to make that decision.
I’m very intuitive, everyone’s…we all roll different, but I need to put the date in my brain and let it sit for six months. Then something will digest and synthesize. Gosh, I use my board a ton.
Amy: Yeah, can I add one thing to it?
Amy: In complement to the board, I don’t know if you do this too but an advisory board, super helpful to also have an advisory board.
Jennifer: And don’t get them mixed up.
Amy: Yes, they’re not the same thing, right? We have an advisory member here. Armando’s right over there. He’s been extremely helpful to me on a number of aspects of the business. You don’t have to go to your board for everything.
If you have an advisory board, for example, you have, let’s say three CMOs, two CROs, and somebody else. When you domain specific questions, you can also hit those people and get their point of view too. I actually…
Michel: I think you guys like people more than me.
Michel: I thought about having an advisory board, but I’m like, “Another group of people I have to deal with?”
Amy: We’re easy.
Jennifer: Power to the people, extroverts at the table. Introvert CEOs, less people.
Jennifer: Automation, AI.
Michel: I don’t like people.
Jennifer: One of the things, I inherited my board at PagerDuty, and I’m currently building out a board and to a point of looking for complements amongst the investors and the founders’ skills sets. How we really build a board that will help take us in to the future.
One of the things I’ve seen in a lot of early stage boards, I’ve been a director of over 10 boards in my career, is an accidental habit of delegating a decision to the board.
As a board member, the last thing you want to see is the CEO that delegates a hard decision up. Share the big decisions, sure. Get them engaged, no surprises. Make sure they understand the challenges you are facing, warts and all.
A good habit to get into and someone else gave me this tip to give to another young CEO that I was working with, start your sentences at the board meeting with “We’ve decided,” or “I’ve decided.” Not “What do you think of?” Welcome to rat‑holing. “What do you think of this?” or “What do you think of that?”
That sounding board conversation is better one‑on‑one outside of the board meeting. The board meeting is about talking through big strategic issues, making sure everybody is in line around the fundamental business drivers in the business that you’re focused on, your line around the outcomes, and making sure you keep those things separate will make your board members happier and enable them to be more effective and help you more.
We’re going to run out of time here. One of my pet peeves about panels is when people get up and talk about how shiny and awesome they are, in perfect at everything, and make you feel like a complete impostor. I thought we would talk about some of the stupidest, biggest screws ups that we’ve made.
One of the things that I’ve learned at PagerDuty from our engineering community, in addition to really what DevOps culture brings to an organization, but also how decisions have to get distributed to the edge. Like the command and control hierarchy, the way companies were built historically, the way I learned to be a leader of Procter & Gamble a hundred years ago etc. are totally outdated.
Dinosaur convention doesn’t work anymore. When you are letting anybody in the front line of an engineering organization, making a decision in real time while some things breaking for instance, you have to treat those people with a high level of empathy and respect.
One of the dumbest things I did early in my days at PagerDuty was were in a SevOne, I don’t know if you remember in 2016, when one of the biggest DNS providers was attacked in a distributed Adidas attack and half of the cloud went down. Netflix was down…Big companies were down, Gmail was down for a while, etc.
We had a disruption and it was going on for a period of time and I was worried we were going to get press cover. So I went in to the incident war room, I was like, “Hey guys, pick up the pace.” Like, “How long is this going to take?” That is now infamously referred to as the executive poop n swoop.
Jennifer: Right? Imagine these folks in the room are killing themselves to try and fix this under time pressure. They are not at all confused about the impact that this could have on our business and our customers, and I come in and make them feel like shit. Right? Like, good job.
Empathy and really under…Empowering people to make those decisions on the edge, do them in real time and really understanding the boundaries of what my role is when we are undergoing a major incident, I am not command.
There is an instinct commander whose power usurps mine. The last thing I should be doing is making people feel bad.
Amy: Poop and swoop.
Jennifer: Yeah. Executive swoop and poop.
Jennifer: Step away from the swoop and poop. What about you, Amy?
We were good citizens and we put that line in so that any time the page was delayed and we were the last ones to put that line in, we would show up. Sergei emails me one morning at 3:00 am and says, “You are slowing down the entire web.” That is heart attack time.
That is like, urghh. The next morning, we are frantically trying to figure this out. My CTO in…
Jennifer: We should have the community.
Amy: Yes, we should have. We should have. Long story short, I did, roughly, the same thing. It was because somebody’s stress response was so different than mine. A lot of times, people, when they are under crazy duress, respond differently.
This guy cracks jokes. That’s his coping mechanism is to crack jokes. Otherwise, he said, he would cry if he wasn’t cracking jokes.
Amy: Which I did not realize, but I was like, “Why are you joking?” I got in his face like, “Are you not taking this seriously?”
Jennifer: Did you make him cry?
Amy: He did not cry, but he shrunk into himself. I was like, “Ooh that probably wasn’t good.” After the whole thing happened, I went to him and I said, “I think I screwed up. I think I made it worse for you.
Can you help me understand what you were thinking while this was happening? I will try and I’ll do better next time. Can you help me understand?”
That led to a whole thing on our team now of going through when talking through stress responses by team. The whole eng team sat down and everybody explained, this is my response to stress.
This is what I look like when I’m under massive stress and here’s how you can help me. We recorded that down. We actually have it on a list.
When people see other people going to that mode of urghh clench, they know OK, this person cracks jokes. This person cries. This person gets super quiet or this person has to go on a walk by themselves because they need to process it.
Now we know how to support each other better as a result of that screw up.
Jennifer: Michel, what about you? Any good lessons learned? You don’t screw anything up, do you?
Michel: Oh, my God. My mistakes are like existential.
Michel: I found my company. My co‑founder and I put in a little bit of money. We hired one developer. We had a prototype. Got lucky and ended up raising a series A. We raised $7.6 million. Now, we have to go build a team. I basically made every mistake you could make in the next nine months, but I’ll point to two.
I felt a lot of pressure to hire fast. I was super convinced we a found a gigantic market. Really convinced that nobody else saw the thing we saw. I don’t know who else is founding here, but some ideas are really, really defensible and they’re such unique IP that no one can steal it.
A lot of software ideas are just obvious and we win by being first.
Then somebody rips our idea off and it’s 80 percent. The biggest mistake in the company that has taken me years to unwind it, we hired our first five devs or first couple devs. Our dev team wasn’t working. You know the one pizza rule?
Michel: We kept scaling, engineering. I’m like, “I’m not getting enough features. There must need more people.” Essential thing I focus on now is, never scale anything until the first thing is working.
We’re going to do a SWAT team on verticals. We’re going to get a couple of deals. We’re not going to scale anything until we get three or four of those working. I didn’t scale sales in turn. We’re still not scaling that fast, because we have to find the repeatable motions.
Literally, it probably took me two years to recover, to actually figure out we had teaming issues. We had process issues. We had architectural issues. We had code issues. I read all the same books all of you as founders all read, and I’m still making all those mistakes. I almost killed my own company by being so aggressive to grow, because I didn’t diagnose the problem accurately.
Jennifer: I think a great saying is ‘hire slow, fire fast’. You are going to make a bad hire. I’ve made bad hires and I’ve been at this a long time. The most important thing you can do is, the minute you realize it, move quickly.
By the time you can see what a bad hire is doing to your organization, people underneath that person have been suffering for three times the amount of time.
Michel: Make the function work before you scale it.
Jennifer: Hire slow, fire fast. Make the function work.
Michel: Make the team work with the smallest number of individuals that you can make it work with. Then you can onboard everybody into a functional organization. You don’t screw up your culture. You don’t screw up your code base.
Jennifer: I don’t want you guys to miss whatever exciting thing is happening next. There’s no timer here, but I think we are…Is that right? Am I out of time or do we have more time?
Woman: More time.
Jennifer: How much more time do I have?
Man: Over five.
Jennifer: I’m over five!
Jennifer: Well, on that note, thank you to whoever the useful counter is. Thank you very much.