How to Grow Alongside Your Startup: Chathri Ali on Going From Employee #10 to COO
Episode Transcript
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Alicia Thomas (00:03):
Hey, I'm Alicia and you're listening to Non-Founder Crew, your insider guide to surviving and succeeding in tech startups. Hey crew, welcome to another episode of the Non-Founder Crew Podcast. If this is your first time tuning in, I'm so glad you found us. And if you're a returning listener, welcome back. I hope you've been finding value in these conversations. Today, we're talking about what it takes to actually grow your career inside of a startup. Not the polished LinkedIn version, the real version, the “figuring it out as you go, saying yes before you know how” version. Because as you can see, most career advice is written for founders, but the majority of us aren't founders. We're the people building alongside them, trying to grow to understand where we fit as the company changes around us. Today's guest knows that seat better than almost anyone I've come across.
(00:54):
I'm excited to introduce you to Chathri Ali. So Chethri joined subscription platform ReCharge as employee number 10, before the funding, before the structure, before anyone really knew what the company was going to become. She grew from the first go- to-market hire all the way to COO, and she was there when the company hit a $2.1 billion valuation. After that, she went to Klaviyo where she saw the company through their IPO. And now she's a founder herself building Accel Health. It's a smarter physician recruiting platform that she co-founded, using everything she's learned about building from scratch to solve one of healthcare's most persistent hiring problems. So what I love about Chutthri is that she's not talking theory. Every single thing that she shares in this conversation, she has lived through firsthand. The good, the uncomfortable, and the stuff most people don't say out loud. This one is for anyone who has ever wondered how to make themselves indispensable, how to grow with a company, or how to know when it's time to move on.
(01:52):
So let's dive in. Chelthree. In 2016, you joined ReCharge. It was a small, bootstrapped, Shopify subscription app. I'm curious what drew you to the company and why you decided that was the one you're going to bet your career on.
Chathri Ali (02:10):
Yeah. So for me, it was partly that I knew one of the co-founders there, and I actually worked with him, the co-founder and CTO at a prior startup. So he was a known entity. So I knew if things go wrong or if there's a challenge, at least I know one person inside the company that I could chat with, but ultimately he was not the one who hired me, was actually the CEO. So it was pretty cool. I actually found a job on a website called Built In LA. So there's built in New York, built in Chicago. At the time, I was looking at different startups and went to the website for built in LA and found this company called ReCharge, and they were looking for a marketing associate. And for every job I was applying for, I was looking at the about us page and I noticed, "Oh, hey, I know that guy." So I just called him actually on a sell call and just said, "Hey, I see you're hiring." And then he said, "Classic, I'm busy, but I'm not hiring for this role.
(03:04):
It's my other co-founder. You should come into the office, talk to him. Things work out. We'll move forward." So that's really how it came about and spent two hours inside the office with the other co-founder, Sheen, the CEO. And from there it was, let's take the leap of faith because frankly, that's the case with most startups. You don't really know what you're getting yourself into and you kind of have to experiment and see what works and what doesn't work.
Alicia Thomas (03:32):
So I'm super curious. You went from the first go- to-market hire, then you went and you were the head of growth, and then you grew into a COO role all in just a couple of years. How did your role expand? I mean, that's quite a trajectory in terms of your career growing alongside the company. How did that manifest?
Chathri Ali (03:52):
So the entire time I was there, I was reporting to the CEO. At the time, there was just 10 of us. I was employee number 10. So to say I was reporting to CEO just meant we sat next to each other and would talk about what was going on in the go- to-market side. And what ended up happening was I started out in a marketing role that was why I was hired. But eventually four months into the role, the CEO asked me, "We're getting a lot of demo calls." And the two people on sales right now, including him, so him and one other person were inundated with calls. So he kind of rolled over and said to my desk and said, "Do you mind taking some sales calls? Can you just jump on a couple per day, as many as you can take? We just got to get these people through the door." And I said, yes.
(04:39):
And I think that's what got me to each new role, which was just saying yes and figuring it out afterwards. And in a startup that's still small, no role's perfectly defined and you have to be okay with that uncertainty. I don't think everyone would've leaped into this opportunity that was undefined. For me, I just said, "Well, they trust me enough to do this next step. Let me just do really well in that role." And then I did well. And then we ended up hiring more people after sales got bigger, marketing got bigger. And then eventually we end up hiring vice presidents for each of those functional areas. And then it became obvious, I can't just do one area, I should just oversee multiple areas. So that's where the COO role came about from was, you know each of these areas so well, you should be the one to hear from these vice presidents of what is working, what's not working, and then kind of be the voice to the co-founders saying, "Here's what we need to focus on or change or iterate on.
(05:46):
" And that I think was the biggest lesson I carry today, which is just say yes. You can figure it all out after the fact.
Alicia Thomas (05:54):
I love the just say yes. I feel like that is such a common thread between people who are early and successful. Just raising your hand saying, "I can do that and going and figuring it out. " So I'm also curious, the company was bootstrapped for a while and did really well, but you didn't have any big VC checks, probably not any rapid hiring sprees. What limitations did you feel when you were building the machine or building the organization from the constraints of being bootstrapped?
Chathri Ali (06:23):
Trying to make big bets. So things like sponsorships at these e-commerce conferences or having more than one to two people attend, everything was an expense. Every dollar was accounted for because of being bootstrapped, you have dollars in and then immediately dollars out. So understanding where to make the right bets and all of that came down to ROI. And oftentimes it was our first time doing a sponsorship or first time doing an event. And so we just got scrappy. So there was a happy hour, perfect example that we did around Shopify Unite. This is 2017 or 2018, I believe. And it was a happy hour we wanted to host around the Unite Conference. And so we decided to partner up with two other partners to split the costs. So as a bet, it was just a third of the cost for us. And so I was able to advocate for the fact that we negotiated, we split the cost, and it was with actually Klaviyo and Privy.
(07:22): So two Boston companies that we split the cost with. And actually, no, it was Smile. It was Smile. Smile, Klaviyo and ReCharge. And those bets ended up becoming a success. And then we could take that success and say, "This worked, here's what the ROI was. Now let's next year invest more." So a lot of it was just making hard choices of where to put your dollars and then using the data after the fact to figure out, okay, we can do this again, or no, that was a dud event.
Alicia Thomas (07:57):
And so you went for five years with no funding, at least when you were there.
Chathri Ali (08:01):
Yeah.
Alicia Thomas (08:01): When-
Chathri Ali (08:02): Four years. Four years.
Alicia Thomas (08:03). Okay.
Chathri Ali (08:04): Yeah.
Alicia Thomas (08:05): When the funding did come through, I'm curious what changes the company made or you were able to do differently. Maybe there were things that held you back previously. Was there a big change when it suddenly became funded?
Chathri Ali (08:17): Yeah, I think this is at the time, and this was not just exclusive to ReCharge. I think Klaviyo and other companies in the e-comm space also went through this. Actually, frankly, all startups went through this, which was 2020, 2021. We had outside macro factors impacting each startup. So things like COVID, things like the Zerp era, where it was really easy to fund at the time or get funding at the time because of those low interest rates. So for us, that was why we raised. Not that it was easy. It was good timing for us. We had really good metrics. We were category leader.That's what you love to invest in as a VC. So it was an obvious investment for Summit who was our series A partner who invested at the time. And then 2021, we had three other VCs invest. What changed was we no longer had to second guess, can I put a dollar here or dollar there?
(09:18): We just kind of started placing chips around the roulette table respectively and to hiring. Yeah, to your point about scaling up where we had a pinch in customer success or a pinch in sales, man, we could use a couple more AEs. We finally opened the floodgates and started to hire. And two, on the leadership side, we were able to meet people with the salaries that they commanded because of their experience. So we got greater leadership, made more bets, and then scaled up the team.
Alicia Thomas (09:53): When I think about your story, something that I'm immediately curious about is you had the founders and they built a product. Really everything else around that, you kind of grew up. I'm curious about the dynamic with the founders. Very much like they are the folks that own the company, but you have a lot of authority and a lot of responsibility. How did that dynamic work for you?
Chathri Ali (10:18): A lot of trust, a lot of trust from both sides. And I think that's why I was able to step into the COO role. I mean, even the founders and myself at the time, we don't know what a COO does. Even in different companies, the CEO role, COO role looks different amongst Stripe as a COO at the time that I've very much looked up to. Her role was different from the COO at Facebook and different from the COO to Shopify. So that role is pretty fluid, but the way we made it work was we had a common understanding of these are the things that you are the authority on. And because of that, you had the decision making power. And so because of the trust we have, we're going to just let you execute. And so that's what we did. And again, I had leadership that was reporting into me.
(11:08): It was the same one layer down. I looked at them and I said, "Sales, marketing, that's your area of expertise. I'll probably only lean in if something's off to our quarterly goals, but trust upwards, downwards." And then just if there was something that was broken, really instant communication. Constant communication was key. Also, fun fact that we didn't talk about, ReCharge was remote from day one when I started.
Alicia Thomas (11:40): That's a big factor in this story.
Chathri Ali (11:42): Yeah.
Alicia Thomas (11:42): Yeah.
Chathri Ali (11:44): So open communication all over Slack or Zoom, that's really hard to do unless you have great leaders and team members. Totally.
Alicia Thomas (11:54): Did you ever feel moments of tension? I mean, one, you're remote, so you're not in the same room normally. I mean, I think a lot of you were in California at the time, but were there moments of tension where you're like, "I have authority in this, but I've got to figure out how I navigate things, especially with the founders."
Chathri Ali (12:15): I mean, I think the tension came from there's a lot of ideas, there's a lot of people advocating for whether it be a new product feature, whether it be we really need to chase after this particular customer while other folks might think it's a bad fit for us. So there was a lot of people advocating for certain things like features or even people, "I want to hire this person." So for us, it just became around going back to our operating principles, our decision making principles, and even higher level, our culture. Does this make sense? So from a product perspective, it was, we want to do the right thing for our customer. Is this the right thing for the customer? Well, if a certain feature only helps one or two customers, maybe that's not the right decision based on our principles of doing the right thing for most of our customers.
(13:13): So for us, it was also hard to do remotely. And so the tension I would say mostly came from in person. We would do quarterly. Once COVID died down and even before COVID, we would do quarterly planning as a senior leadership team. It was healthy tension. Again, with the advocating for what each department wanted within a specific budget and a certain timeframe, there was a push and pull. And so everyone had to navigate between that tension, but again, it was healthy tension.
Alicia Thomas (13:45): Let's talk about something that I feel is not openly discussed with people who have been in positions like yourself, and that is negotiating for yourself. I'm very curious, you were an early employee, the company went on to get a $2.1 billion valuation. As things went along, how did you negotiate your equity, comp, even your title? Did you feel like you were very savvy or was there things you had to learn along the way?
Chathri Ali (14:12): This was the first company I'd been at that had institutional funding at the size that we did, and also the first company where I had even the opportunity to advocate for myself. I actually did more advocating for my team first, to be honest. We went from bootstrap to being a venture backed company, and we had the opportunity to assign some values for what kind of equity package folks would get. I actually spent more time advocating for certain team members than myself. For myself, we didn't have CARTA at the time. We didn't have CARTA data to fact check against for a certain role. Does this make sense? We had really old school salary data. We're Googling. There was no AI. So for me, I felt less empowered to advocate for myself back then versus now. And now as a founder and understanding how to have that conversation with my now employees.
(15:14): But back then, I honestly, again, going back to trust, I just kind of went with, I trust that this number's right, and I trust that if it's not right in the future, I could probably have a conversation about maybe a refresh at some point. But from my standpoint, very fair. And then anything that wasn't fair for my team members, that's where I advocated for them.
Alicia Thomas (15:38): So when you look back at that first year, is there any advice you would've given yourself to have a better outcome?
Chathri Ali (15:45): Have less imposter syndrome.
Alicia Thomas (15:48): Oh, man. Yeah, me too.
Chathri Ali (15:53): No one knows what they're doing that early, and you're not the only one in the room who has no idea how to take that first step. Everything I was given was the first time for everything. I can't even name how many things we did for the first time. So I think giving myself forgiveness that we're all just figuring it out together, that's, I think, the advice I would give myself in the first year. It's okay. You're not an imposter. You deserve to be there.
Alicia Thomas (16:25): Many of us still to this day, when you get to even be senior, you have those moments too, right? I mean, I imagine you're a founder now. I'm sure you have moments of that as well, which is ... Oh, it's so relatable and it's so human. After the funding came in, did you ever have a moment where you felt like even though things were good, you were kind of being watched for performance. I know a lot of times when funding rounds come in, there's a lot of changes that happen and a lot of looking at things and assessing if we've got the right team on board for the next area of growth. And was that something you felt or you thought about?
Chathri Ali (16:57): At the time, our entire team was changing. The whole company was changing. And I think one thing that we learned was every three months, the company's going to look different. So every three months after the funding happened, we were all looking around the room saying, "Am I still in the right place? Am I in the right position? Am I on the right team? Am I surrounding myself with the right people? " And so I think that's the biggest thing that for me, I was never really concerned about performance per se. It was more, I was concerned about just making sure that the culture of the company continued to get better and better with every single addition of a new hire or new leader. I was actually more concerned about that. My own performance, of course, not perfect. There's some personalities as I'm being transparent that you just don't get along with because they're new and they're maybe going to change the alchemy of a team.
(18:00):And my hope as a OG is kind of what I would call myself is that they either make the collective whole better and see the good for what was there before they came. So yeah, for me, it was more making sure I navigated those personalities the right way and being welcoming. It's tough to come in from the outside after a funding round and after you have the first X number of team members who all are really, really close. So for me, it was more about, okay, making sure that I was adapting and understanding this is a whole new chapter. So was I perfect every day? Absolutely not. I'm sure there's a lot I could have done differently, but at the time everything was new, everyone was adapting, some better than others. And I could raise my hand and say there were days where I was probably a little bit stubborn and bullheaded to try to keep things the same way as I used to be and didn't want to adapt, but eventually came around to it.
(19:02):And at some point, you look around and you realize maybe this isn't the place I want to stay, not sure if that's where you're going with next, but at some point for everybody who's a early stage employee, you think about your "tour of duty." You're dropped into this chaotic Lord of the Flies environment. You don't realize that it's Lord of the Flies while you're there. You don't realize you don't have things like proper shoes or shade. This is my Lords of Flies analogy. And then all of a sudden you get funding and you get shoes and shade and running water and like, "Oh, this is just nice." So you have second level problems that you start to think about. And eventually, yeah, everything's built and your tour of duty is done. And so for me, that's kind of what the case was after five and a half years.
Alicia Thomas (19:56): It's like you've been reading my questions
Alicia Thomas (19:58): My next one is right in that kind of wheelhouse. So you left ReCharge after five years and the $2.1 billion valuation, then you went to Klaviyo, you worked there for two years, saw them through their IPO. Both are really big milestones where you can celebrate and be at the top of the mountain cheering on. What told you that it might be time to leave after those events? Was there anything in particular or any moments where you're like, "Hmm, might be
Chathri Ali (20:24): Time?" Yeah, I like to think that I'm a builder, and so when I stopped building, that's really when I saw the opportunity to build elsewhere. So at ReCharge, I built the entire go- to-market engine, had it in a good spot, really incredible leaders who were running each of those departments. And then there was absolutely still more to build, but to me, I look at impact. Am I still going to have the same amount of impact with every hour I put in? Am I going to feel the same impact coming out for me as I reflect on my time day after day, month after month? And at some point it becomes, no, I don't think I'm going to have the same amount of impact or even ego-wise, influence. Let's be real. I think with a bigger company, you have less and less influence over time. And then at Klaviyo it was, and this is public info, basically the team, the leadership team there was really trying to move back to a hub approach at Klaviyo.
(21:28): So was my time there done? Was I still building there? Absolutely. My time was not done, but I had the opportunity to move to Boston. And for me, it was a lifestyle choice to not do that. And for me, it was, okay, if I don't stay at Klaviyo or/move to Boston, what would I do instead? So it was actually my choice. Having gone zero to one at ReCharge, having done one to a hundred at Klaviyo, that was a moment where I said, "I think I'm ready to become a founder. I'm ready to be a founder."
Alicia Thomas (22:02): How long did you sit with that decision? Did you have to really think about it or did you have a moment where you're like, "This is what I got to do? "
Chathri Ali (22:11): I knew after ReCharge, I wasn't ready to be a founder. That much I knew was true. I was also ready to not be the front lines of being senior leadership. It was kind of nice to take a different position at Klaviyo and let the founders and SLT at Klaviyo make the hard decisions there. So that was a nice change of pace. And what really clicked for me was seeing the decisions that were made by the founders and leaders, seeing how I probably would've made certain decisions, whether it's the same route or a different route. Not to say I kind of knew the right answers, but it felt like after doing those two journeys, I knew so much more about how to think through these decisions. And frankly, the founders at ReCharge, the founders at Klaviyo, some of the smartest people I've ever worked for, I respect them so much.
(23:02): I learned so much. I'm so grateful. I didn't think I could do this founder experience without having gone through that. So that's really what clicked for me, which is, could I learn anything more from another founder at this point? Maybe, absolutely, but not that I couldn't fill in at the margins by being a founder myself.
Alicia Thomas (23:22): What was a moment where you look back and you thought to yourself, "If I ever did my own thing, I do this differently." Did you have some of those moments where you're like, "I learned my lesson and we'll never do that.
Chathri Ali (23:34): " I could take another hour long podcast to answer this question. That's everything. That is absolutely everything I took from those experiences and have applied to this startup that we started two years ago from who do I want to be my co-founder? This is a marriage. Having seen other marriages and seeing their marital, air quotes, conflicts, who do I want to get in the ring with that we're not going to get bloodied during our debate or fight that we can have a logical discussion. And I always knew the VP of engineering at ReCharge and I, we very much got along. We very much had the same type of style in terms of leadership, approach to startups, just mindset about how to build. And for me, it was, okay, I think I know how to pick the right co-founder and my other co-founder happens to be my husband.
Alicia Thomas (24:38): You literally are married.
Chathri Ali (24:39): I'm literally married. Yes. So even thinking through that, is that even the right decision for me? Do I want to mix business and personal life? Beyond that, the lessons around how to hire. How do we think through our first hire, second hire? How do we think about venture capital? Do we want it? Do we want to be bootstrapped? There's so many, so many things I learned. I'm really glad I got to be part of this speed bumps when I wasn't a founder. And not to say we haven't made mistakes here, but man, we learned a lot.
Alicia Thomas (25:13): Is there anything you do differently as a founder because you were formerly an employee who has seen how it all gets made? Is there anything that top of mind, like 100% I do it this way or that kind of thing?
Chathri Ali (25:28): I'm not the smartest person in the room. I can understand that I have an ego, but I can also separate my ego from reality. And so something that I've done a lot is just ask more questions and not assume I am the one and only authority on a particular subject. So frankly, and I know everybody says this, I've hired people who are smarter than me, but also I've hired people who I can empower to just own their domain, let them make decisions, bring me in to either inform me or consult with me, but ultimately they're the decision makers. That's huge. I think for me is that I'm able to see what has transpired in my previous life and have tried to do the opposite. And that's worked out really well.
Alicia Thomas (26:19): For someone who is an early employee, say number 15 at a startup, they're really ambitious, they want to scale with the company, they want to have impact. What advice would you give to someone in that position?
Chathri Ali (26:32): Just say yes. Honestly, try to be so informed on the product you become indisposable. So whether it's the product, product knowledge, like in your own area, become indisposable. And I don't mean that in the sense that you just have job security because you know everything. It's more the leaders lean on you to help or make a decision on a particular topic on either the product or the customer or if it's data, the data, just become an expert. That's what I would say is do the same thing I'm doing, which is like ask more questions, talk to more people outside of your area. Oh gosh, that's huge. Put yourself in a different department. Ask. Make the ask. Can I go spend a Friday afternoon in customer success and answer a few tickets if it's not required of me? I just want to learn. Or even flip side, can I jump into engineering and maybe sit in on a dev standup and understand how they go through their priorities and figure out what's most important?
(27:40): I would say that cross-pollination is so key and that's what makes you indisposable. It's a lot of team members know who you are. You show that you care. You show that you know the product, which I think I come from two, three companies that are product first. If you can become this product expert at employee number 15, you're going to have a pretty long career, at least for the next three to four years, and have probably the opportunity to go into different positions because you'll be known as that malleable team member.
Alicia Thomas (28:14): You're somebody who's curious and you care. I think that goes really far for people. I have the same experience, like people who drop into other meetings and want to learn about the other teams. When it comes to making decisions and placing bets, they're so much more informed because they understand what else is going on in the business. Definitely something that people should be thinking about.
Chathri Ali (28:33): Context is everything.
Alicia Thomas (28:35):Absolutely. What have you learned about working with challenging leaders that you might be able to share with our audience? I know we've got a lot of people who struggle with how to work with folks that are different than them or that are in a senior position. Anything you've learned along the way?
Chathri Ali (28:52): You have to learn how they make decisions. And a couple things. One, a lot of the leaders I've worked with have a little bit of an ego and two, oftentimes they're not self-aware. So you have to figure out how to navigate around them and having the humility to say, "That's okay. It's okay. That's how they operate. I'm going to have to operate around them in a positive way." So with that, how does that person make decisions? Do they want to hear from 10 different people before they make a move? Do they feel that they're the authority and you have to convince them otherwise? So I'm saying this because I've dealt with multiple different founders, and so you have to understand their style. And if you think you have the same playbook for each leader, it's just not going to work. So one particular leader would like to talk to experts who are outside of our company, who are the experts in their domain, who ran billion dollar companies and they were the authority for that co-founder.
(29:59):Okay. Well, let's figure out who else we can get to influence based off of their own authority that maybe they haven't talked to before. Or another co-founder might be more data backed and they're just very technical. Maybe we bring data to them to say, "This is actually what's going on on the ground. This is why we need to pivot this way." So whether it's influence, whether it's thinking about data or even that they like to get more personal. So they like to go on a walk or they want to have a chat after everyone's left the office and they prefer to really get into the topic offline. I remember at Klaviyo actually, one of the co-founders sat with an engineer at the pub across the street just to really talk through something related to the API and they hashed it out and had a beer and the decision was made.
(30:55): So every co-founder's different, you have to figure out their style.
Alicia Thomas (30:59): Fabulous advice. Well, thank you so much for coming on this show and sharing your story. You are certainly a builder and I am so excited to see how you build out Accel Health.
Chathri Ali (31:09): Thank you for having me. This is great.
Alicia Thomas (31:15): Thank you for listening to Non-Founder Crew. If you want more insights, learnings, and stories from the trenches, sign up for my newsletter by going to www.nonfoundercrew.com. And hey, listen, if you know a friend who could stand to hear this advice, send it to them. See you next time.