Today, I'm connecting with Anna Prell, VP Operations at Ivo.
Laura Nicol dials into Anna Prell, VP Operations at Ivo.
Anna reminds us why being an operator is a) so damn exciting and b) the ultimate leadership testing ground:
"In a startup, you can be your own version of a founder. You’re the founder of whatever it is you’re in charge of. You keep testing, learning, and scaling until it works."
Inside this conversation:
Want to connect with Anna? Find her on LinkedIn.
Also mentioned:
Pre-interview chats:
Connecting with Anna Prell, VP Operations at Ivo:
[Note: This transcript is AI-generated via Descript. Please expect typos]
Laura: [00:00:00] Welcome to Calling Operator a podcast, dialing into the stories of startup operators. Tune in as they share their incredible and often challenging journeys of building and scaling startups. Operator connecting with Anna per VP of Operations at Ivo. Anna gets mentioned in so many different operating circles from what it takes to create a customer success or legal function, or essentially who is somebody that just runs at fires.
And in this discussion, she said a quote that actually I really wanna highlight here because it shows the opportunity that comes with operating inside tech startups. A startup, you can be your own version of a founder. You're the founder of whatever it is you're in charge of. You just keep testing, learning, and scaling until it works.
End quote. And I absolutely just love that. I just think there's such an opportunity, which is I guess why I am learning through this podcast every fortnight. [00:01:00] But back to Anna. For Anna, this journey started when she made that transition from corporate to startups in 2019, and she's also been living in the Bay Area since 2020.
At Forage, she moved through four roles, customer Success manager, chief of Staff, which is actually the role she moved over to the States for, to the CEO, VP of Ops, head of Customer Success, plus navigating the acquisition and integration with. The new owner, EAB, we talk about all of this and then how she figured out her next right fit when she decided it was to move on.
That next fit happens to be Ivo, which is a Kiwi founded legal tech company. So it takes her legal tech experience and then also all the lessons she learned at Forage tied up into a nice bow that she can learn and build again. So I hope you enjoyed the conversation today. Huge thanks to Katie Newnan who actually was interviewed with us for episode four.
So go back through the archives for the [00:02:00] episode and also Tom Brunskill, who's the co-founder of Forage. Thank you so much for your time and helping shape this episode.
Anna, welcome to Calling Operator. How are you doing?
Anna: I am so well, it's Friday afternoon and I can't think of anything I'd rather be doing than speaking to you, so thanks for having me.
Laura: Oh, that's so nice. Thank you for giving me your Friday afternoon. So I wanted to touch on something really lovely that Katie mentioned in the pre-interview chat, and she mentioned you're an eldest daughter and the fact that she named that as a thing I found really interesting.
So I'd love to start by painting the picture of what does she mean by that?
Anna: I think there are some things about me that are typical of an eldest daughter, and there are actually some things that aren't. I think what's typical of me as an eldest daughter and probably what she was referring to is I am [00:03:00] a people pleaser at heart.
That is both a good thing and a bad thing, so it can work in my favor and it can work against me. I think at its best, I find that one of my strengths is. You know, building relationships and connections with people because I figured out early or maybe naturally how to connect with people and empathize because it drives me to make other people happy.
At its worst, it becomes a bit. Overwhelming and can be toxic. And so being an eldest daughter, I think that comes from a position of responsibility within the family and wanting to be the best in the family. Leading by example. I think where I'm. Perhaps not a stereotypical eldest daughter. Um, where my sister, who is the youngest daughter actually trumps me, is she's often taking care of me 'cause I'm booking flights a week before I'm meant to go somewhere.
I'm forgetting that [00:04:00] I've made a reservation and then making another one over the top of it. My organizational skills in my personal life somehow are not the same as my organizational skills at work. So that's a weird quirk.
Laura: Same. I actually called mom on the 1st of September 'cause I was like, mom, the move's officially this month.
I'm so overwhelmed. And she was like, have you canceled your electricity bill? Have you canceled your contents insurance? And I was just like, of course I haven't. She was like, ah, that's such a Laura thing.
Anna: Yeah, I'm like, this isn't helping. I feel like that's my sister. She'd be like, why haven't you booked your flights home for Christmas?
And I'd be like, well, I'll do it eventually.
Laura: Yeah. And talking about, uh, booking your flights home for Christmas. So you moved from Australia to the US so you're actually joining us from the US today. But the beginning of your career started in Australia and it started at Herbert Smith Free Hills, which I understand is a very prestigious law firm.[00:05:00]
I'd love to know what solid training did that give you, that set you up in your operating career?
Anna: I am so grateful for the training that I had as a lawyer, and I am biased, but I continue to believe that people who have been trained as lawyers make excellent operators. Why is that? I think that's because in a law firm.
There is this very specific mix of being customer facing and so needing to figure out how to manage your time, figure out how to be really punctual, figure out how to, again, solve problems and everything is framed around that. So everything is in service of these clients and. Law firms hold their employees to an incredibly high standard, and sometimes that can be problematic, and that's a whole different conversation.
But that high standard teaches you [00:06:00] early on the benchmarks for being able to prioritize, being able to keep yourself organized so that you can meet the requirements, the deadlines of the client laid underneath the structure of. Legal frameworks, and so that creates another kind of structure that you need to work within that.
Plus, I think there's a bit of a, a social network aspect to it as well, so you're usually surrounded by people who are also holding themselves to a very high standard. And so I think when people step out of that environment into an operator space, they're used to high levels of pressure. They have the customer facing skills, and they learned really early on how to prioritize.
Laura: And something actually you didn't mention in the eldest daughter piece was carving your own path. You went from being a lawyer to being a startup operator across two continents, and actually very early, making [00:07:00] that corporate to startup transition. And often you're kind of known as somebody in the ecosystem that made that transition early.
So can you take us on that journey?
Anna: Yeah, it was not planned. It wasn't part of the plan. Again, maybe this is something that makes me an atypical eldest daughter. I usually don't have a plan. You know, if someone asks me what my five year plan is, I balk and I dunno what to say. Coming out of law school and then going into Herbert Smith Free Hills, I guess I always knew it wasn't going to be my forever path.
But one day around four or five years in, I sat up and I, I looked at. The people around me and I, it just felt like that wasn't going to be my path for the rest of my life. I was terrified because I didn't know what I did want to do, and so I just decided to explore and I spoke to a bunch of people. I had a lot of [00:08:00] conversations.
I interviewed for a bunch of different other types of careers, so I. For a hot second, I thought I was going to go and be a consultant. I thought I'd try a career in the government. I thought I'd try a career in the not-for-profit space. I thought about going in-house as a lawyer. The amazing thing about not having a plan, although that was an incredibly stressful period for me, because I, I felt like I had no direction, I didn't know what I was gonna do, is I just allowed myself to sort of explore all those different options.
And then Tom Brunskill, who was the co-founder of Forage, is the co-founder of Forage. Because he'd heard that I was having all these conversations reached out and said, I have this opportunity as a customer success manager, and joining a startup was not something I'd ever thought about before. I didn't know anyone who was doing that.
It was so daunting. He will tell you that I originally said no, which is true, and I think. To be really vulnerable about it. I was just too scared and [00:09:00] I didn't know what that was gonna look like. It was a very unfamiliar path. I didn't know anyone else doing it. And then I reflected on it and it was the one thing, the one conversation that I had had with someone.
Tom was a friend of mine at the time, but even still, of all the conversations I'd had with everyone, that was the one that kind of stuck to me and felt the most compelling. And also I was excited at the idea of working with him. And so I turned around and came crawling back and I begged him. To reconsider.
And I was so lucky that he said yes. And I, I think in some ways, the fact that it was so unknown, it was a blessing in disguise because I think maybe if I had have known then the rational part of me would've said, no, this is gonna be a lot of work and scary. And so I'm kind of lucky that I didn't have too much of that in my head.
So it was more fear of the unknown. But I, I jumped two feet in and basically didn't look back. [00:10:00]
Laura: You give a lot of time to mentoring and mentoring people that are either trying to follow in your same path or actually just being a startup operator. What is the most repeated piece of advice you give?
Anna: I think varying different versions of throw out the rule book.
If it makes sense to do it. I think I've learned that sometimes, especially in a startup environment, actually what you know, or what you think can, you know, can work against you. And just trying to take everything from a first principles basis and then trust your gut is usually the best way to figure out the specific solution for the specific problem.
You are trying to solve. And having just been here at Ivo for two and a half months, I sometimes find that [00:11:00] where I can trip myself up is relying too much on what I knew or what I've learned from Forage. And instead of just saying, well, here's how we did it at Forage, so this is how we do it at Ivo, it's more about.
What have I learned in terms of how to assess a problem, how to assess a risk, how to figure out the solution and using that skillset to come to the solution rather than just take the playbook and repeat it. And again, that's very against the training that I had as a lawyer, where it's all about playbooks and precedent and in fact.
I think working with Tom, he's the best example of someone who did an exceptional job of leaving behind everything he'd learned as a lawyer and, and taking everything from first principles. And so I always have his voice in my head in terms of just take it from the ground up first principles. So that's what I'd say.
Laura: So, forage. Forage. So [00:12:00] for anyone listening that hasn't heard of Forage, what is Forage?
Anna: It is an educational technology company and. We, I say we, but they create virtual job simulations, so that gives college students the opportunity to try a day in the life of a software engineer or an accountant or a lawyer.
So Forage works with Fortune 500 companies across the globe like Citibank, Walmart, to create these simulations of particular jobs for college students.
Laura: And over your time, you helped them scale to a hundred million earners and there is so much to unpack 'cause you've had multiple roles. I think where I'd like to start is, so your roles have been, you joined as a customer success manager, then you went to chief of staff, VP of Ops, and then head of Customer Success.
But during this journey, you actually moved from Sydney, Australia. It was [00:13:00] Sydney, wasn't it? Yes. Yeah. Sydney, Australia to San Francisco in 2020. COVID. Yeah. Like that's a brave, brave thing to do.
Anna: Yeah, I classically didn't really think too much about it beforehand. I think I've always wanted to live outside of Australia for a certain period of my life and.
Certainly when I joined Forage, I had an idea that that might be on the cards moving to San Francisco, and then when it really became a possibility was when I moved into the chief of staff role and it made more sense for me to be. In the US as the kind of center of the business. And so it did get delayed by COVID.
So I did have to wait a little longer than I had originally planned. But in the end, I'm grateful that I went after COVID rather than before because I think setting up a life in San Francisco would've been so much harder had [00:14:00] COVID just been happening. So in a lot of ways, I feel very lucky that I moved over afterwards, and it's been really fun to watch.
San Francisco kind of come back to life over the last couple of years in a post COVID environment.
Laura: Yeah, totally. Let's actually talk about the environment and the differences of the environment, because the Australian ecosystem, it feels small, right? And then drop you into San Francisco. Paint the picture.
What was it like?
Anna: It was very different three and a half years ago than it is now for a number of reasons. So firstly, at that time, a lot of people had actually physically moved out of San Francisco to get away from COVID, and so the city itself was kind of a ghost town, which was jarring. The other thing.
About San Francisco is, it's a very small city with a very small financial district, and so it's not at all like New York or even Sydney, and a lot of the tech companies are actually in Silicon Valley, which is kind of an hour south of the [00:15:00] center of San Francisco. And so I think I was initially struck by, it's kind of a more virtual envir.
It was back then a more virtual environment. Then Sydney was where everyone was very much in office in Sydney, and here it's a bit more dispersed, but then that has changed, especially in the last six to 12 months, there's a real push to move back into the office. So with Ivo, for example, we're five days in an office in the center of San Francisco, and I think when I moved over initially we were.
Right in the tech bubble wave, and now we're in the AI wave and it feels even faster, even bigger, and starting to feel like a more in-person sort of city, which has been really exciting. But yeah, I was overwhelmed. I remember going to my first tech conference and just feeling completely blown away by the sheer number of people.
That was a big change from Sydney.
Laura: I can only imagine like how daunting that would be. I'd be like, [00:16:00] ah, I'm suddenly scared of people.
Anna: Well, especially after COVID where we were living inside the whole time and then suddenly when conferences ha started happening in person again, it was really quite confronting.
'cause we, we all had the fear of being close to someone and here we now were in conference halls, which were enormous with tens of thousands of people.
Laura: So you've seen Forage start in Sydney through Y Combinator, then UNSW founders, 10 x, how do you say that? 10 X 10 X accelerator program? Yeah. Yeah. And then raise multiple funding rounds.
And then it was acquired by a US education firm, EAB mm, last year. Mm. So how do we wanna unpack each role and transition and what would be most valuable in terms of the lessons to share today?
Anna: Wow. Um.
Laura: Huge question.
Anna: Huge question, particularly because loaded again, again, in my scattered approach to all of [00:17:00] this, each one of those roles when they came up was sort of an opportunity that I jumped at not really knowing what I was getting myself into, because all I knew was law and legal practices, and so I didn't know what being a customer success manager at Forage.
Meant, and actually there was a short period of time where I even pretended to be a product manager and not a good one at that. I, I did not hold that role for very long because we didn't have a product manager. And I think if I'd known what a product manager was, there's no way I would've put myself in that position because that's a skill that I, I don't know.
But I think on the flip side. I took on the chief of staff role before knowing exactly what that was, at a time when I think chiefs of staff were kind of a new thing anyway, and so therefore not having a clear idea of what it was meant [00:18:00] that I was able to kind of build the rollout and Tom and I made it.
What worked for him and what worked for me and the business at the time. So really the experience of being at Forage in that early stage was a matter of just, again, kind of running towards the fires and figuring out what was needed. So the reason I ended up in the chief of staff role was because I saw.
Things that needed to be done. So for example, I was offering to help Tom review customer contracts I was offering to help do interviews for various roles. Even though I was not confident that I knew how to do that, I just figured I could give it a crack and help him. And so, because I was driven to help and to take ownership of problems that the business was facing.
Eventually, he said, well, you're doing all this different stuff. It doesn't make sense that you're in a customer success role, so. Why don't we build out a chief of staff role? Then when I'd [00:19:00] done that for two years, I had built a HR function. I had built a legal function, and so then it made sense to move into a VP of operations role.
So we built this VP of op operations role, and so I think the way that that journey happened was me finding opportunities. Putting my hand up to do it where it wasn't even necessary. Just doing the things. And that's part of being an operator is seeing, okay, there's something going on over there that I think needs fixing or solving or building.
I'm just gonna go and have a crack at it and see how I go, and then that could lead to a whole new adventure.
Laura: Operator, I have a quick ask. This show is all about creating space for tech operators and learning how to be a better operator along the way. Please help me reach the builders doers and multipliers behind great founders by hitting, subscribe or follow wherever you're listening.
Thank you, operator. Let's double down on [00:20:00] moving from a chief of staff to, I guess, leading and owning a function officially 'cause that comes of managing teams. And had you even at that point, managed teams before? And if no, like what did you learn?
Anna: So much. I think people really underestimate how hard it can be to manage people, even for seasoned managers.
It's a skill that you need to hone and develop, and I was very aware of that at the time, and again, I. Tried to come at it from a first principles basis. So the first person that I managed was our director of people. I was pretty open with her that I had no experience or background in hr, and actually she was the expert and I was going to be learning more from her, which was true because I didn't know how to run an HR [00:21:00] function and.
By positioning myself as more like a sounding board for her or someone who could help come at the project she was doing and the challenges she was solving from the perspective of the business meant that I could manage her in a way that would help her and, and we could grow together rather than trying to do it from a top down approach.
And. I sort of ran with that and learned lessons along the way about how to give feedback and how to receive feedback. And as they say, sometimes in startups, you've gotta be flying the plane as you're building it and that that is very much what my experience of learning to manage teams was.
Laura: Yeah, totally.
And trial and error and through the error being open to that feedback. So what was the biggest aha moment of like, ah, this is how I can get the best out of people? [00:22:00]
Anna: I dunno that there was an aha moment necessarily, but at some point along the way, I figured out. Actually, I think maybe this is really present in my mind right now because I am in a different environment now in Ivo and managing people who've been at Ivo for longer than I have and know the product, know the customers, know the business way better than I do, again, is kind of.
Leaning into what does this individual relationship look like? And managing in my experience is absolutely not a one size fits all, especially because I managed a bunch. So I managed a legal function and an HR function, and then a customer success function. And it's definitely a more. Draining experience as a manager to treat every individual person as an individual person and try to [00:23:00] build a relationship with that person rather than saying, this is my management style.
It's more work for sure, but I find that I get more out of people by remembering what is it about the way that we interact. So I think a really tactical example is my one-on-ones with people, especially at Forage, were always very different. Some people I found worked really well with a preset agenda where they'd come to me with a list of things that they wanted to talk about other people.
It worked better if I did the agenda. Some people had trackers that we worked off. Some people was more like, I have three issues I want you to talk me through. It wasn't always just a matter of you tell me what's best for you and then I'll do that. It was more, how can we work together to figure out what's going to be most productive for you in this role?
And so I think just over time, managing [00:24:00] a lot of different people taught me that.
Laura: Yeah. And like being flexible in your approach to meet their needs.
Anna: Totally. And also making it. A matter of importance that a large part of any management relationship is firstly setting clear expectations and then secondly, having a really clear feedback loop.
I think the setting expectations part is really hard because it can feel really daunting, especially as a first time manager to sit down with someone and say, here's what I expect of you. 'cause that feels. Aggressive and it can feel confronting and especially if that person maybe is older than you or maybe has more experience than you, which again, with the director of people ops, Olga, she had way more experience, but I have no idea what I was doing, but I came in as her manager.
And [00:25:00] so having that, here's what I expect. Conversation is really. Confronting. But if you don't do that, then anytime you feel like they aren't meeting your expectations, it's really unfair to then give them feedback because they, how could they have expected to know? So I am a big believer in, in having that conversation early, even though it feels really awkward and challenging, it makes everything so much easier from that point.
Laura: So let's get into the acquisition. I actually was listening to voice notes from Tom Co-founder this morning, and he shared a story that during the acquisition, there was a moment that you guys were up between, I think it was like one to 3:00 AM every morning. You're working a hundred hour weeks. There was this one day that really stood out to him that.
It was 3:00 AM He was at this point that he was just emotionally exhausted by the whole thing. Stop, start, stop, start. Is it happening? And you just turn around to him and you just were [00:26:00] like, Tom, I've got this. Go to sleep for two hours. I will run this meeting. And I just wanna like set the tone of like how instrumental you were through the acquisition.
So with that framing, where do we start?
Anna: The hardest thing about the acquisition was we had no idea how long it was going to take to do the deal cycle. And usually when you do a project, you have a timeline and we thought we had a timeline. And as is. As far as I know, always the case with acquisitions.
There's always a little tricky issue that pops up, that extends out the timeline and you're suddenly doing diligence for a lot longer than you had initially anticipated. And for Tom, who felt the full burden of managing this acquisition, resting pretty much solo on his shoulders, it was just. [00:27:00] Becoming exhausting trying to run without an end in sight.
If, you know I've only gotta run for another kilometer, that's much easier than you gotta just keep running and, and we'll just tell you when to stop. And so I figured that my role. I don't have a finance background, so our VP of finance was really instrumental in, in running the financial mechanics of the deal, and Tom was kind of running the negotiations.
I saw myself as how do I stitch this all together and keep this thing afloat while we're all running? And maybe that's partly kindness. Maybe that's partly, again, run towards the fires, but it was just this operator mentality of. What gaps need to be plugged and how do I do that? And so. That example of the 3:00 AM call where everyone was at their wits end, at the end of their tether.
But I could tell that if Tom was at the end of his tether and he didn't have the energy to keep going, then the whole thing would fall apart. And [00:28:00] so I had to tell him, I had to say, I'm gonna figure this out. The first priority is you go to sleep. So I guess in that moment I was like, what's the potential risk here?
The potential risk here is that actually he just runs out of. Steam in this incredibly high pressure environment, and I had no confidence that I was actually gonna be able to figure it out. But I knew I would find a way somehow, so I was like, I'll just shut my eyes and try.
Laura: Yeah. What's so magical about this operator founder relationship and partnership and hearing it from the founder's perspective is actually, it was actually just so nice, but we should also say that when you're running an acquisition, you're kind of trying to do it all while having an uninterrupted employee experience.
That's like including supporting Tom, that's managing your own team, that's working with the lawyers, hiring, implementation, and also building relationships on the other. Side, so with the new company. So walk us through that experience. [00:29:00]
Anna: Yeah. It was juggling so many balls, which is life in a startup, in an early stage startup anyway, but it was really tough.
Tom was really big on leading. With transparency, and that was one of the best things about him as a founder and a leader, and I tried my best to emulate that as well. That's really tough when you're doing this whole other thing, which is ultimately a win for everyone. The acquisition and the deal was in the best interest of the business and was a good thing, but not being able to talk about it felt disingenuous.
And so we had to go at it with this mentality of, we have to remember that this is in the interest of the business, and that's kind of what. Was the guiding principle all the way through. I think the other thing was everyone who was kind of in the tent [00:30:00] on the deal, we really supported one another. We knew how important it was that we were working together as a team.
There was so many moments where we had arguments and it was usually late at night, but. The strength of that was we always reset and came back the next day, and there was never any like tension or grudges that got held for a long time. We knew that it was just the heat of the moment that was making it difficult, but we were fortunate enough that we had such a great working relationship.
I think again, because we all did operate from a position of kindness that made that easier.
Laura: Was there one moment that felt really hard that actually leapfrog your growth quite substantially.
Anna: A few moments, and one of them was that moment that you mentioned earlier where the negotiations felt like they might grind to a halt because of a particular legal or financial issue that the parties just couldn't come together over.
[00:31:00] There were moments where it really felt like. We might be at a dead end here, and you find yourself kind of scrambling and scraping the bottom of your brain to try and figure out how to get around it, and the only way through at that moment when I felt so far out of my depth was just to continue.
Talking about it, and again, that team mentality and coming back to first principles and trying not to let the technical aspects of it really get out ahead of us. And I think in a way, because I'd never done it before, again, coming into it. For the first time without expectations was also helpful because you could approach it as well.
This is just another problem that I've gotta solve. And yes, it's not a problem I've solved before, but I've done that before.
Laura: Those relationships that you built on the other side with the EAB team, what were the lessons that you took from there around advocating [00:32:00] for, I guess, your company, but the new company within their business?
Anna: Yeah, it's an incredibly disruptive thing for a company that's. Being acquired to suddenly become a part of this other organization. And we were really lucky that the culture of the two organizations felt very aligned and that I think was part of the deal thesis was that. There was a mentality towards what we were building, but also how to build it on the inside.
That meant that it made it much more seamless than it could have been. It took a lot of patience, I think, to learn everything that. Was specific and unique to Forage and figure out how to insert that into the existing ecosystem on the EAB side. And so there were a lot of people that I worked very closely with at EAB, who just exercised so much patience around trying to [00:33:00] understand exactly how everything worked because even though Forage was a relatively uncomplicated business.
When you dig into it, it's very nuanced and the way that we've decided to do things has developed and evolved over a period of six years. And then to pick that up and just try to plug it in, you gotta undo some things. And it does require going back and saying, what's the context behind why you set up Salesforce in this way?
And EAB was. Very good at just unraveling the full thread to understand why something was the way it was, and then figuring out how to take that and put it in the system without completely breaking it.
Laura: So the acquisition went through, the integration begins, but then there came a time that you were making your next career decision.
So you've been through so much with Forage. Walk me through the process of making that career [00:34:00] transition and decision.
Anna: It was so hard. It was definitely harder than when I decided to move from law into a startup because forage felt like something I had created and something I had lived, and the relationships that I'd built were so important to me and a part of my identity, and actually the fact that I'd moved over.
To San Francisco with Forage. I had this existential crisis for a hot second where I was like, I don't know who I am in the US without forage. And that was a weird thing to think about.
Laura: This identity in the US with a company. 'cause your identity was so tied in like why stay in the us? Like how did you even know what was important to you after Forage?
Yeah. Like how did you start to gain some of that clarity through Probably a lot of tiredness too, if we're honest.
Anna: [00:35:00] Well, I wasn't so tired by the time, so it was a full year post the acquisition that I actually made the decision that I was going to start exploring o other options and, and so that made it hard too.
It was almost like the EAB forage part of my career was a shift in job and career itself. And so I had found another home in EAB, so then it felt like I was leaving that as well. So it was less being really tired and more like, well, could I see a future for myself here? And in a, in a lot of ways I could, but I think I just had this underlying gut feeling that I wanted to go.
Back to building something and I wasn't exactly sure what that would look like. And I had these two visions of am I gonna be in operations or am I gonna be in customer success? And how do I figure out which one of those I like as if it was some sort of [00:36:00] binary decision, and do I wanna stay in the us?
And I think I just. Tried again to have as many conversations as I could, reach out to as many people within my network as I could and sort of figure it out along the way. And some of the early conversations, like I look back on one of the earliest conversations I had with an investor who I had asked if I could just sort of chat to her about what my next steps might be.
Looking back on it, it was such an unstructured conversation. I'm mortified that I had the audacity to speak to this. Incredibly experienced investor and just be like, would he reckon? But I sort of had to go through that in order to figure out what I would target myself towards,
Laura: give us like a fly on the wall view.
What became that piece of advice that was so valuable that actually would help shortcut somebody else? I know it's quite unique, but is there anything?
Anna: I really [00:37:00] think it was a matter of. Taking each conversation on its own merits, and rather than trying to think about, I'm gonna go after a particular opportunity.
What is this opportunity going to look like? And I think the challenging thing for me as a non-US person is I don't have as many signals in the market here that are as. Recognized as someone who's been to college here and come through and got all the signals. I don't have a recognizable university here, and I had a lot of imposter syndrome around that, and so I had to just put that to one side and treat each conversation as an opportunity in itself.
Laura: And ultimately Ivo became the company. So what was it about the co-founders that made you feel like it was the [00:38:00] right fit? And also just going back to what you said, like you were hungry to build again. Like why did you think you could make an impact there? Firstly, the product,
Anna: it felt like this wild, incredible confluence of my legal background and my tech startup background.
And once I started digging into the product and seeing what it could do, it felt so compelling to me, and I could just tell from both my experience as an in-house lawyer, but also building the legal function at Forage that this was a. Potential game changer for the way that contracts are negotiated and stored and reviewed.
And so the first thing for me was I could really stand behind this product. And I was very fortunate to be in that position at Forage [00:39:00] that I felt really deeply passionate about what we were doing there. And so then as soon as I could. Recognize that feeling at Ivo. That was a huge green flag. And then in terms of Min Q and Jacob, the co-founders of Ivo, they were both incredibly low ego, incredibly smart.
I felt a level of transparency that. I really appreciated and, and has definitely proved true today, two and a bit months in as the types of leaders that I would want to work with. They felt like people who also deeply cared were deeply ambitious, but were in it for the right reasons and felt relatable also.
They were Kiwi, so felt very close to home in terms of the impact that I thought that I could have. I recognized a lot of the. Same challenges in a slightly different [00:40:00] manifestation here, especially around building a customer success function for enterprise clients and building a people operations function for a rapidly scaling business.
And those were moments that I had been through at Forage. I definitely don't think that just because I saw those moments at Forage that I could lift. My learnings from there and just apply them here. But there is something about the muscle memory of having been through it that I felt like I could at least come in and provide a perspective that might help to build that out here.
Laura: Yeah, that's so exciting. And especially a Kiwi business hiring somebody in market, like, I'm not sure how many of you're in the office at the moment. Is it still relatively small?
Anna: There's around 30 to 35 of us. Okay. In the office here, and then a few people who are in other cities in the [00:41:00] us So it's a relatively big team.
Yeah.
Laura: So how are you going to continue figuring out what good looks like as you scale there?
Anna: That is a really good question, and I think I am still figuring that out. In fact, I think that is something that. As an operator, you should never stop figuring out, because I think as hard as it is, I do think the goalposts change and should change, and maybe what good looks like at Series A is different to what good looks like at Series B, and as the team grows.
Those expectations grow and, and I think this is what I saw at Forage as well, there's this tight knit group of early stage employees and suddenly, you know, you might not have as much access to the founders as you originally did, and you might not have exactly the same flow of information. It gets harder, it gets harder to [00:42:00] follow what's going on as things spread and become more complex.
And so what good looks like early on is. Everybody's working together directly and running at this thing. What good looks like as you get larger is now you're in more of a pod system, for example. And so again, you might become more narrow focused, so that's gonna change what good looks like. And I think the, a sign of a really good leadership team for me is a team that keeps.
Popping up and reevaluating that, and also setting really clear expectations. So if what good looks like does change, flag that. And you've gotta tell people because otherwise they, you can't expect them to just jump up and meet your high expectations if you don't tell them what they are.
Laura: Yeah, totally.
And like you're only two and a half months in, so we're gonna be kind here. So we're all gonna watch your journey for the next year. But in terms of like a growth area for you that you're working on [00:43:00] over the next year, what will it be?
Anna: I think one thing that I learned from a few of my colleagues at Forage that I am still working on myself is being a ruthless experimenter.
What I mean by that is. Figuring out what your hypothesis is for solving a particular problem, running a really tight test on that hypothesis, evaluating the results, and then rinse and repeat. And that's a very kind of product focused approach to building. But I don't think it has to just live in product land.
And as I think about how. We are building out a world class customer success business here at Ivo. I think the way that I wanna approach that is, here's an experiment that we're gonna run. If it works, great. If it doesn't, then tweak some things and run it again. And [00:44:00] Tom. Built that mentality into the team at Forage in a really impactful way.
And I think the lasting impression that that has left on me is in a startup, you can be your own version of a founder and you are the founder of whatever it is that you're in charge of. And what the founders do, they just run experiments and they do it until it works and scales. And so you can do that and be an owner and be a founder in your business.
And that's what I wanna work on here at Ivo.
Laura: That's so great. We'll have to talk in a year's time. Yeah. And unpack which experiments failed and which worked. Yeah. Give us those lessons. Okay. So you've been in the US for five years. From your vantage point, what's your outlook for the US tech ecosystem and what's the opportunity for a NZ companies within that?
Anna: The opportunity is enormous. Things are moving so quickly here, and that's a real change that I've noticed from [00:45:00] Forage is the speed at which companies are moving now because of AI that can easily feel. Like an environment where it's harder to win because in some way everyone can do it, but in another way it actually means anyone can do it.
So therefore, I actually think the opportunity has broadened, and I'm seeing that here in the US and in Australia, where people are finding new challenges. New problems to solve, new businesses to build and doing it really fast. I'm really excited about that. So I think we're just at the beginning. I think sure there's gonna be a lot of change and a lot of that change will be scary and uncomfortable, but I think it's better to try to lean in and see what it can do for you, then worry too much about where [00:46:00] it's gonna hold you back or pull you down.
Laura: Talking of fast, we're in the final segment of the podcast and we're gonna do a quick lightning round. So just say what comes to mind? Operator, what's a decision you made early in your operator journey that you're most proud of?
Anna: It's a cliche, but I think the decision to go and work in a startup, as I said, in a really vulnerable moment, for me being very scared of doing that and then doing it anyway, or you know, crawling back to Tomara, asking him to give me a chance.
I'm really proud that I took that leap.
Laura: I'm proud of you too. Thanks. One to three operators you admire and why.
Anna: I really admire Amy g Glancey at Atlassian, who's she's the chief of staff at Atlassian. She is a rockstar.
Laura: I'm her biggest fan girl.
Anna: Same. She's incredible. I love what she's built. I love her approach.
I [00:47:00] love how personable she seems, even though she's done this incredible thing. I love listening to her talk. She's probably top of my list. Another one would be. Clara Ma, who built the Chief of Staff Network here in the Bay Area, when I first came across her, she basically just had this kind of like a newsletter on what it took to be a chief of staff and she was working out of On Deck and now she's turned it into a full on business herself, and I think she's done an incredible job of that and has built this incredible network that a lot of people turn to and really value.
Laura: I also love her mission of like finding a chief of staff for every exec or something like that. I've probably butchered it
Anna: totally. I just so wholeheartedly believe that every exec needs a chief of staff and it means such different things for different people. But yeah, I, I wholeheartedly believe that [00:48:00]
Laura: favorite US tradition.
Anna: I love Fleet Week. So here in SF there's a week in, I think it's in October, where they do this big air show. This is so unlike me, and this answer will surprise almost anyone who knows me, but I love. That air show is just such a crazy thing to me and so wild, what they do with those plans, and it really does take over the city because it, it is just so loud.
I also have become a big NFL fan again, A lot of people find that surprising, but I find it a really entertaining sport.
Laura: That's a good way to make friends as well. Yeah, that's true. I'm like excited for that. For Melbourne. I'll be like, oh, I'm suddenly the biggest sports fan. Yeah, exactly. So then a piece of advice you'd love to pass on.
Anna: It's gotta be just. Lean into trusting your gut. I think [00:49:00] particularly a lot of women operators that I speak to go through the journey of learning how to do that and find it so empowering once they do. I wouldn't say that I'm particularly good at it myself, and I'm definitely leaning into it, but I just think it's such an underrated skill is to really, really lean in and listen to what you know.
Laura: So true. It's very underrated. And lastly, who should I get on the pod next?
Anna: Great question. I would love to hear Alicia Wells, who I worked with closely at Forage, and she has now gone on to lead the customer success team at Holter. She. Led our UK team at Forage and so she built that side of the business and she's a rockstar.
Laura: And she's doing the same in the UK for Halter or has she come back to No, she's back. Back in [00:50:00] Australia. Oh, Australia. Oh, awesome. Yeah. Yeah. Alicia, expect are we Little message from me.
And we haven't actually touched on this subject at all today, but to round us out, building and scaling companies is hard. You've been through many a long week and hard things. What's been one mindset or daily practice that's helped you stay grounded?
Anna: I think running. I really have gotten into running in the last.
Three years, and especially forcing myself to run without headphones, so I'm not constantly trying to listen to something else and just reset by forcing myself to just go for a run with no headphones, ideally with someone else, and never thought I'd say that, but that has been a game changer.
Laura: So, perfect place to end the podcast.
Thank you so much, Anna. If people wanna connect with you, where's the best [00:51:00] place? You
Anna: can connect with me on LinkedIn or reach out to me through Ivo. My email address is anna@ivo.ai. I would love to connect with you,
Laura: and that's a wrap. Today's episode was recorded by me, your host, Laura Nichol, with original music composed by Steven Shelton.
If you enjoyed this episode, please give us a follow and we'll see you next time.