Today, I'm connecting with Shipra Mahindra, Principal Product Manager at Octopus Deploy. Let’s just say—Shipra’s peers can’t stop raving about her. She made her mark as the first product manager at Canva, working closely with co-founder Mel Perkins and the early mobile team. Shipra takes us through the highs, lows, and many celebrations that came with launching and scaling Canva’s first mobile app. She shares how she found her rhythm as a product manager and the lessons she's learned, both as a human and a product leader, during rapid growth at Canva, Xero, Creatively Squared, and now at Octopus Deploy. And when she’s not leading product, she’s showing how New Zealand can be an incubator for world-leading, world-class companies as a Partner at Phase One Ventures.
Today, I'm connecting with Shipra Mahindra, Principal Product Manager at Octopus Deploy. Let’s just say—Shipra’s peers can’t stop raving about her. She made her mark as the first product manager at Canva, working closely with co-founder Mel Perkins and the early mobile team. Shipra takes us through the highs, lows, and many celebrations that came with launching and scaling Canva’s first mobile app. She shares how she found her rhythm as a product manager and the lessons she's learned, both as a human and a product leader, during rapid growth at Canva, Xero, Creatively Squared, and now at Octopus Deploy. And when she’s not leading product, she’s showing how New Zealand can be an incubator for world-leading, world-class companies as a Partner at Phase One Ventures.
Connecting with Shipra Mahindra, Principal Product Manager at Octopus Deploy:
[Note: This transcript is AI-generated via Descript. Please expect typos]
Laura Nicol: connecting with Shipper Mahindra principal Product Manager Act octopus Deploy Shipper's journey started as the first PM hire at Canva the first person that Mel co-founder of Canva hired to be an extension of herself and she's since worked in some great projects great companies and is now a product leader at Octopus Deploy I think what's really key to take away from this interview today is how respected shipper is in the a NZ ecosystem When I published a teaser post for this episode there's comments like easy one of the best if not the top product leader in Australia New Zealand Also a hashtag Knew her before she was cool So very very excited to bring you this story today please give the podcast a follow and rating if you enjoy this episode also we're changing things up today And we'll wrap things up in a fun rapid fire set of questions inspired by my previous guest Harry Dale So thanks Harry for um for building this podcast Alongside me is a podcast for operators and I'd love to hear from you if you've got any additional ideas enjoy the episode
welcome to Calling Operator I'd love to hear who are you beyond your job title
Ships Mahindra: I'm a mother to a six year old a wife a daughter I'm also a first gen immigrant into New Zealand I've learned this new term actually I'm a 1 5 gen immigrant which I explain a bit if you like I'm a Harry Potter fan and I love walks on the beach
Laura Nicol: So explain your 1.5
Ships Mahindra: I came across this article mentioning immigrants and generations So a 1 5 gen person is someone who's moved into a country as a child but just around or before their teenage adolescent years So they develop a lot of their personality and will combine you know their originating culture with the country they've landed in into that culture they'll keep a lot of their native language but then they'll also know their way around the new culture really well as an adult essentially they'll be a melting pot of the two So there's first gen there's 1 5 which is a new term for me and then there's second gen and so on third gen onward
Laura Nicol: So then who or what made you the human you are today
Ships Mahindra: I guess the defining moment where I sort of feel like that my personality shifted so traditionally I would just call myself a really good girl Followed everything said yes to all the good things you know said no to all the not so good things all of that right And that started to subtly shift and change when I did my MBA back in Sydney towards the end of 2013 we moved to Sydney and 2014 the whole year it was the year of my MBA and then started challenging a lot of my beliefs and what I thought was the right thing to do And also the way I sort of behave in the world
Laura Nicol: where did you think you were going to end up at the start of your career versus where you are now
Ships Mahindra: I don't know there's this belief and a lot of folks coming in you know from school into university always think oh yeah this is the only choice I have You know this is the make it or break it If I don't choose right now my career is going to be miserable for the rest of my life and that's such a myth even in my first year I was a Physics math nerd I chose to do engineering and I'm like yeah I'm going to do electrical or mechanical and then after that first year which is your common year of engineering a change my mind and chose software engineering Mm just from that year one I started to change What my thoughts were on my long term career and so yeah coming out of uni I'm like okay cool I'm a software engineer but I always knew long term like I don't know when but I will probably move out of being a software engineer possibly into at that time it was felt like a very linear path but felt like you know people management was the only option at that time But again going into it getting that experience working two three years into it I'd again change that view already as I learn more and more every day the shape and the path changes slightly And it's almost like I'm always on the discovery path of I think I might do that next but Something will happen or something will change and I'll get new information and I'll change that again I definitely thought when I started I'd be like a CTO type person you know that's my goal And I'm like nope that is no longer my goal right now I'm very much aiming towards starting my own thing it's a startup whether it's a fund I'm not sure yet but I will start my own thing in the next couple of years
Laura Nicol: so That's so great you did an MBA and then you've landed various product roles which you're now at Octopus Deploy what's like an interesting story or insight to unpack from that journey
Ships Mahindra: building on to the question that you've just asked before you know no one stays in the same role or the same career path or even the same career or the same industry for a life I think a career is only a choice for the next maybe five years maybe 10 years and you move through different phases That's a thing that I learned obviously with experience other interesting insights I have is around before when I started and this is probably true for a lot of folks actually who start as graduates or some of their first job roles you know you take everything personally and if something goes wrong it's your fault that's how you think about it But over time i've realized that's definitely not true There are multiple factors that cause something to go wrong or something to fail and even when given feedback
Laura Nicol: Mm
Ships Mahindra: Always take that with a grain of salt you need to be really clear about what your role was in that and how you could have made that better But you know everything that goes wrong or every fault that happens with your product with your code is not your fault essentially those are some of the things that I've internalized over my career and I think the last bit I'd add to that is and this took me a while So this took me until pretty much the last year or so to figure out where building a team culture where the team together can perform at the highest levels is way better for Solving problems making progress you know achieving your goals all of that then hiring A players kind of don't work together or just are out to prove themselves essentially took me a while to figure that one out But yes
Laura Nicol: yeah I love that your first product role if I'm correct was Canva So being the first PM at Canva I had a chat with Mahesh ahead of this call and he yeah gave me some insight that you were essentially the first person that Mel Perkins Co founder of Canva trusted to be her first PM So I'd love to unpack that story and maybe some of the projects that you worked on at Canva
Ships Mahindra: the funny story So after my MBA I knew I wanted to go back into tech I knew I didn't want to go back as a software engineer And I felt like a product management role was a really good fit because I could get a bit of the strategy and interact with the other parts of the business and you know get some of those work on some more gre y and ambiguous problems over a lot of not a lot but sometimes you know as a programmer you're working on very technical highly defined problems Anyway so I was looking for a product management role but in Sydney in Australia the path is not very simple that way because if you take a top management school in the U S it's pretty much a guaranteed career path lots of companies high product managers that have just graduated out of their MBA program but it's not so true for Australia or for New Zealand for that matter even at that time I was talking to Atlassian was the big deal at that time the biggest the hottest tech company to work at And even talking to some of the senior PMs there expressing my interest No one really wanted to hire a non experienced PM They were all importing their PMs who had a few years experience from overseas so yeah it was very hard to find a product role is the short of that kind of got lucky with Mel and Canva because they were Mel is very much if you don't know her personally she's very much wants to shape the way of working So it's not just about building her vision but it's also about how she wants to go about getting there And she wants to shape A lot of that and shape the company culture and all of those things And so she really didn't want anyone with lots of PM experience to come and you know roll out their own things and the way they do things you wanted someone to fit into the Canva way of doing things Which was pretty ambiguous at that time right I don't know what that meant I think I met Mahesh at one of the local meetups and I met another lady Chris who was there at that time as well She's awesome too And you know just sort of applied thinking oh yeah I'm looking for a PM role so you know why not Yeah I remember the whole interview process was pretty intense compared to anywhere else I'd interviewed at that time I think maybe closest to the Google level where you have five different interviews to get through so Google was another company that applied then at that point as well and I remember the first two rounds went okay And then the last round was at half a day in their office working through a particular problem It was an activation problem they'd given the data the qualitative quantitative data access to a lot of their resources that they would have internally to figure out you know how we can improve activation for Canva And it was a half day challenge I had to come up with recommendations analyze data come up with recommendations and give a bit of a presentation
problem in this way specifically or worked on activation or any of that I knew the concepts but I mean it all went well I guess Ultimately they loved what I had to hear and that experience was quite intense But the biggest part that I remember was at the end there's the you know presentation and then the Q A The Q A was supposed to last about an hour and went on for about three hours My husband actually thought they'd like kidnapped me or something ridiculous like that They were like messaging me but my phone was switched off and he was really worried
Laura Nicol: just a second I'm just getting grilled by Canva
Ships Mahindra: yeah like you know it was pretty much the first four or five employees at Canva were in the room feeding off of me asking questions you know and we were just having a really long conversation And I remember there's Cliff and Anna and Zach and everyone was just super excited to have me in the room and and we were chatting away and we were talking about all the problems and what if this didn't work out what could we do next And also the questions like that they were happy to talk to me for three hours and that's probably why I convinced them to hire me
Laura Nicol: That's unreal What year was this and how many employees were at Canva at this stage
Ships Mahindra: Very early 2016 It would have had maybe less than 50 for sure I can't remember the exact number but definitely less than 50 And the folks were split across We had like literally one floor on this in the Sydney office And then we had Manila office which had less than 10 people in it as well supporting us those were the two
Laura Nicol: Incredible So then you got through the golden gates you got in to Canva and then what
Ships Mahindra: and then what so at that time they were building the mobile app but I hadn't quite launched it yet so it was before launching the mobile app And so they decided to first as an onboarding exercise I did work on the activation problem for about a month or so the best way to onboard us just to do the work that's what I got to do We pushed out a bunch of experiments and improved activation by about two or three percentage points which was awesome a good win And then moved on to the mobile app and delivering that I think I spent about two or three months working with the team uh getting to launch and figuring out all the things that needed to be done for the launch So in a startup as you probably know you put on multiple hats So it's very much being the tester making sure all the bugs are fixed figuring out which user experience could be more intuitive can flow easily what are features we could improve and working with the engineers to do all of that and designers sorry One of my best experiences was working with uh engineers and designers at that time we were about three engineers one designer and myself kind of launched that mobile app I also obviously did the marketing pieces of it letting customers know doing app store optimization and you know all of that sort of stuff we launched and I think we had maybe day one maybe a hundred users at that point uh maybe less you say that you say that now I remember very clearly I had poured in so much of my heart into it And I was up until at the last minute before we were having the launch party the iPhone launch party So canvas notorious for celebrating every moment so at this moment we were having this launch party for the iPhone app And at 1 a m in a meeting room somewhere Mel and I are sitting revising emails that we're going to be sending out in about two hours U S time zone to our customers about the launch right And so you can imagine that mad last minute sprint to get to launch a week after launch I was told by at that time our growth person that this was a very unsuccessful launch because you know Canva the web app had a few thousand users a day like daily active users And I didn't even get to 1000 downloads I got to a hundred or less I think for memory And he's like how do you consider this a successful launch I'm like uh I think the app didn't break down We didn't go offline That's pretty good Right I like that was one of those hard moments which I was not prepared for my startup journey It felt like such a roller coaster because you put in so much hard work and it's just like nope your app's shit you couldn't get thousands of users on it from day one that's the kind of feedback just the whole week I was so sad and then it took a few people around the company you know including mel herself It's like i'll ignore that person They're really upfront That's just their personality type launch is just the beginning Don't worry you'll get there So everyone else it didn't affect but um Yeah
Laura Nicol: You're like I'm experiencing some trauma around this app
Ships Mahindra: pretty much That was me And from then on I worked for about two years from memory just growing the mobile app team as well as the product we launched the Android product grew it to millions of monthly active users hired a growth person to work with me on it you know all of that
Laura Nicol: Insert celebration
Ships Mahindra: Yeah every quarter was a celebration because we hit a new milestone and it would just feel like we're winning but it's definitely a rollercoaster because you know there were definitely times where we thought we wouldn't meet our goals and it's always hard the thing that I'm most grateful for is the team I had around me as the company grew obviously I didn't get to work with Mel As much day to day but the team around me I remember one of my engineers there's Andrew and Nick Whitteson and make was our designer you know some of the these early mobile folks and Max Sheffler and I'm missing out a lot of names here but there were a bunch of these folks who were just amazing to work with And that's I think what made me stay more so than working on the app itself
Laura Nicol: I love celebrating the peers So everybody that's in that pool you know who you are zooming out what do you reckon was the biggest lesson that you learned and took away from your journey at Canva
Ships Mahindra: you go in at a startup thinking this is your chance to make an impact This is your chance to prove that you can build something deliver something of value make a difference in the world shape something from the very beginning Kinda true but kinda not true as well this is my biggest lesson is basically startup is the founder's baby and their child and their baby and their life really And so they have a lot of say in the future whether it's the vision whether it's a long term strategy whatever you can think about right Even the shape of the product even the design Right So you see a lots of feedback from Mel on every little detail of the design And that's actually a good thing because they're the one who had the original vision They know what they want to deliver They went out and secured the funds to make it a real company And they have that right and so you need to become their biggest ally the person they can rely on who can get shit done who can deliver on the vision on their vision not on your vision on their vision you need to be very clear about that going the startup It's not your vision it's their vision And you're the person who's there to help them accelerate them deliver and magnify their impact this is a hindsight learning Let me tell you I did not feel like that when I was working in it So in the hindsight this is my big takeaway So if you're thinking of joining a startup you know keep this in mind
Laura Nicol: just know that so many people listening to this episode that maybe wanting to get into product be having this experience that you had all those years ago of like first product role I'd love to know given it's the founders maybe the founders vision how do you deal with that pushback as a PM especially when you need to almost Disagree and commit
Ships Mahindra: As a TLDR you've summarized it really well where you need to learn to disagree and commit so you might believe in a different direction but until you I think I think one of the things I found really helpful was bringing lots of proof so bringing qualitative and quantitative feedback on things on decisions But also having lots of alternatives there's always a middle ground I'm sort of struggling to think of a good example here But there's always a middle ground where the founder wants something but you want something else And then there's a halfway between or a little bit
Laura Nicol: Mm
Ships Mahindra: somewhere right So you need to get good at finding those as well and the crossover might be yes we'll do that but how about we do that next quarter and not this quarter and we try this this quarter and that will give us a good base to start in the meantime we'll do all this research or we'll go talk to a bunch of users blah blah blah to Get prepared for the thing that you want next quarter T here's always stuff like that And then things always change So every quarter you're rethinking your roadmap that's just normal and in a startup at that early stage you're rethinking your roadmap every two weeks even your iteration cycles are very very short that's one way to deal with pushback but I think Just being okay with the fact that you're there to deliver their vision and you know make peace with that firstly always talk it through So I think a lot of founders even in my current job Paul our CEO who's the founder of octopus even he appreciates anyone playing devil's advocate and walking him through the argument on the other side for a killer choice He really always values that doesn't mean at the end you'll get your way or you know it doesn't matter like cause the ultimately if the company needs to win right
Laura Nicol: Mm
Ships Mahindra: It doesn't matter if it's your way or their way choose something move on make the decision and learn from it That's the best way that company can learn and win in the long run
Laura Nicol: from Canva and getting to millions of users you've had some really great exposure to the scaling journey across various roles from Xero to creatively squared to your current role at Octopus Deploy what are some of those things that you've seen and what lessons have you taken along the way on that journey
Ships Mahindra: Canva was my first and only product role And I really wanted to see what it was like to work in a larger company with an established product management practice and I was hoping I'd be able to learn even more there and that's kind of when I joined Xero didn't quite work out for me from that perspective I think being in a startup and moving fast and making decisions happen really quickly spoiled me a little bit in that sense I lost patience I think in the hindsight for convincing 10 stakeholders to move forward with the thing which is what zero was at that stage you had to convince 10 teams or 10 head of teams or leads or whatever to continue making progress along your roadmap that's mainly why it didn't work out but I did enjoy having more Experienced product managers around and having someone even as a manager and so at Canva again you didn't really have managers A lot of it was up to you you know you make your own career decisions so I'm didn't really have very many experienced managers until much later on in the life of the company that I was there Xero was obviously the opposite We had few really good managers of people who I learned from and a lot of it was around that stakeholder management piece and also bringing the rest of the company along your journey how do you communicate and over communicate and communicate 10 different ways so everyone gets excited by your mission and wants to join you and make you and help you all along the way so a lot of that came from working at Xero even though it was a very short time and then I joined creative squared after that that was very much a five uh well less than 10 percent startup probably you were about seven people in hindsight for that one was a very very short stint It was about less than six months I'd say And the main reason for that was the startup had just hired Too early they were bootstrapped doing really good work but completely bootstrapped So slow growth and very much dependent on the revenue coming in to expand the team they'd hired thinking you know their previous two or three quarters have been really good and they were expecting the same sort of growth to continue for the next three quarters And they were making a bet on that obviously And then based on that they would have hired one like full team of seven or eight engineers plus myself So they hired me first and then sort of gave me the opportunity to then hire my own team But the revenue piece just didn't work out and the founder really just had to be there at that point I had learned that the founder has to be the product person until they can't scale themselves whether that's at 10 people whether that's at 20 people whether that's at 30 people but I think at the minimum your first engineering team needs to be led by the founder because they need to be the PM they need to be the person in the room you can't really outsource that at that point So that was one thing I learned from there Again I'm still in touch with the co founders there and whenever I visit Brisbane they're from there too so I do say hi was one of those very humbling experiences where you know I thought Oh I've done some cool stuff in my career You know I'm sure this would be a piece of cake or not a piece of cake but a different challenge but I'd really enjoy it but didn't quite work out And it was very much like okay back to earth Let's try and figure out where to start again
Laura Nicol: Oh damn brings you to today
Ships Mahindra: octopus Yeah
Laura Nicol: So you're a principal product manager at Octopus and also a partner at Phase One Ventures.How would would you describe your role and growth journey across both businesses
Ships Mahindra: So let's do octopus first I joined as a senior PM when the company was maybe about a hundred ish people and quickly gained trust by delivering on the team that I was on you know moving the metrics in the right direction and all that stuff and setting up just new ways of working the company didn't have a good product management practice at that time So whatever I bought on was very much new to the company Most of the time it got accepted and well received and then based off of that so worked on pretty much a feature team for the first year um to pretty much kind of showcase and lay the path of what good product management looks like then worked on onboarding our first ever real proper enterprise customer for about six to nine months and this is where I started to get exposed to a lot of the sales stuff So understanding the deal understanding contracts understanding pre sale promises versus post sale promises And you know what those workflows and processes look like working a lot with the sales team but from a product perspective to ensure that our first ever enterprise customer had a really good experience of using Octopus and deploying it within their company within their business And then that brings me to my current growth which is working on the next differentiating strategy for our company It's kind of like the next chapter of Octopus the deployment market I don't know how much you know about it but it's quite Saturated and we do want to stand out and differentiate And so we're hoping the stuff that I'm working on right now we're hoping is going to be hot leading within the industry and within the space
Laura Nicol: let's just stay on Octopus Deploy Can you share any strategies that have led to success and what you've learned from failures
Ships Mahindra: I think Octopus is a unique culture in itself It's a remote first company And what are skills that you really need to work at Octopus is your communication but specifically your written communication communication happens asynchronously ideas get shared through written documents like we call them pitch docs or sometimes RFCs So we have different tools for different things to get a decision so one of the things I've had to hone in on is how best do I communicate over documents and Slack to get the team on board get folks excited get the right feedback at the right time and keep things moving and what is the right balance between that and say jumping on a zoom call for half an hour where the call is much more valuable and where it's not and what that means is I've gotten much better at getting my thoughts down on paper but also using that to clarify the problem and thinking through the problem multiple times before sharing that with folks so thinking about all the different aspects of a problem
Laura Nicol: Just for context what is RFC
Ships Mahindra: it's a old school term it's called Request for change but in octopus it means that we are making a decision that could be a one-way door or just a difficult door to walk back from a two video but that's a difficult one And impacts multiple teams or multiple groups of folk it's a written format of how we basically get feedback on that decision and a way to almost strengthen that decision make sure we're considering all its impact and ultimately making the right choice
Laura Nicol: that was learnings from successes and what you're doing successfully there anything that you want to share what you've learned from failures
Ships Mahindra: I think one of the things I've learned is bringing a team along the journey every team has its own subculture and People come together and form this complex web of thoughts and they have complex set of behaviors and aside from individual preferences the team culture also dictates how much they want to be involved early or how early they want to be involved and how much communication is good or bad for example there was a time where I had to hand over stepping into a team temporarily because they didn't have a PM you know I'd worked for them for about six months and onboarded a new PM into the team that we hired The mistake I'd made there is I onboarded PM and gave them all the right context correctly but then the team sort of was left in the dark in a way of what's happening And that caused some low decision making on their part And overall they were just wanting more visibility of What's the transition plan which parts are going to be done by the time you've left and which parts of new PM will take over and that kind of stuff It's the day to day you know I need some certainty kind of emotion coming through and I sort of feel to provide that And it felt very abrupt that one day I was in the team and then one day I wasn't even though in the background they knew this was happening the new PM and I were both in all the meetings for a while and I'd sort of started in meetings handed over the mic to her a lot more but it wasn't obvious still to the team somehow I've done those things before in other teams and it's worked perfectly well other teams not had any issues because in previous teams the subculture is like Oh yeah of course the new here So we should talk to them They just naturally gravitate and I know they will fully take over in a couple of weeks or in four weeks or whatever it might be you know and things like that were more obvious but with this team somehow it wasn't
Laura Nicol: almost like they were looking for you to be that bridge and bear hug that support
Ships Mahindra: exactly parts of that is cultural because at Octopus we understand that the domain that we work on is complex It's not everyone's cup of tea and especially if you've not come from a technical background and you know nothing about software and how built or delivered it's yet quite overwhelming very quickly to understand the DevOps space so we're very mindful as a culture To give lots of space for people to learn and on board So sometimes on boardings can even last for up to anywhere between three to six months because they might just be picking up the domain and learning all the domain concepts and it might take them a while to get to performing part of that is actually just the culture of the company and the way we choose to work and give space to folks
Laura Nicol: And then also you're working as a partner on phase one what work and impact are you having there And what do you love about working with the founders that you support
Ships Mahindra: phase one is a unique one it's not your traditional VC because the goal behind phase one is actually more the goal of proving that In New Zealand we've got lots of talent and that New Zealand can be an incubator to world leading world class companies It's almost proving that out that theory out It's not meant to be VC that grows which is like fund one fund two and keeps on going over many years and generations right it's not about growing that as such when it started it was very much about finding those founders who are super driven to build those world class companies and treat this as their life's work their legacy And bringing them all together showing them what good looks like and helping them connect to folks who have been there and done that so that was the premise of phase one I mean is the premise I should say no it's the premise All through that journey of sort of bounced ideas with Mahesh spoken to a lot of the founders who've come on that journey with us and mentored them on and off But with end of last year we sort of made a more official step forward where I joined them as a partner mainly to help the funds get into an operational rhythm We're closing the fund this month and then post that you know a lot of the stuff is around investor communication startup communication keep the community going and making sure the founders get the right support at the right time and the investors have full visibility of what's happening in the fund that's really going to be my role going forward aside from obviously sitting on the investment committee itself as well
Laura Nicol: could talk to you all day about the operational rhythm of a fund so we should catch up offline off this
Ships Mahindra: a hundred percent
Laura Nicol: in that operational rhythm work are you doing operational work to support the founders
Ships Mahindra: Yeah So what that means day to day is literally checking in with them catching up to see how they're doing see if they need any help So if they're hiring they're on a first ever salesperson Can I get them connected to someone who's done it before Who's built a sales team before in a B2B business and what that looks like Really those kinds of day to day logistics we're trying to get founder chats going as well on a monthly or quarterly basis and bringing in LPs who are also very experienced to share their learnings and their skills with our founders and then just yeah keeping a check on all the numbers and making sure the investments happening at the right time the founders are able to get the money and access the money all of that sort of stuff from a financial perspective And connecting them to other VCs as well So as the startups grow and need more funding we actually are very we work on very small ticket sizes because of thesis that we're proving it's because we don't want it to be a big VC into institutional fund so we're a very small fund we provide just you know a little bit of funding The value the founders get from us is not the money essentially So it's all the other things that we do being there and validating them cause a lot of founders are on this journey alone Yeah They might have co founders so it might be two of them on this journey but they still feel quite alone sometimes And so just being this external sounding board and validating that they're thinking about things the right way Or on the alternative challenging them that they should be thinking bigger and why are they thinking about these other options making sure they're able to confidently move forward with their chaotic startup journey
Laura Nicol: If you had to name one of the most rewarding moments from your time at Phase One what would it be
Ships Mahindra: just when the founders secure their first round of funding that is always the most rewarding and we've had that now for easily more than 10 startups 10 founders I should say sorry have either successfully closed their pre seed or seed with favorable terms like the terms that they're really happy with and they haven't had to compromise at all That is a big win
Laura Nicol: and actually such an important thought partnership area as well that you probably provide
Ships Mahindra: exactly a lot of founders when they go through these negotiations they can't ask Blackbird what to look in a look for in a good VC You know that's not a question they can ask
Laura Nicol: No
Ships Mahindra: institutional VC no matter how friendly they are So this is where phase one comes in we kind of form that bridge because we're not quite fully in that VC space we form that bridge It's like yeah well this is the things that will probably benefit you And don't go talk to that person if they're being you know an a hole
Laura Nicol: I love that we've got theme of bridges today which I'll bridge into our next segment what do you think your super Power strength or genius zone is as an operator
Ships Mahindra: Okay this is gonna sound cliche but it is getting shit done my version of getting shit done because everyone has their own version of it I think but the way I get shit done is making Achievable plans So where you have this big ambiguous goal how are you gonna actually get there I'm the one who builds the plan to get there And I'm the one who's making the small decisions the everyday decisions that gets us there quickly And then as a side effect of that a lot of it is bringing that calm and order to that chaos of getting to a longer Bigger vision and leveraging the team the smart people around me who probably have all the answers and they're way smarter than me Leveraging their skills and their knowledge to move forward quickly as well
Laura Nicol: Mahesh said that was your superpower strength And he also said humble in a sense that it's not about you It's about the job to be done
Ships Mahindra: it's always about how can we solve the problem The next thing what's the next thing What's the next thing How do we get there
Laura Nicol: what do you reckon has been the most challenging moment of your tech career
Ships Mahindra: Oh gosh having so many Okay so I've already mentioned glimpse of it at Canva at the beginning There were multiple moments of uncertainty across that journey and I think even early in my career as a software engineer got challenged a lot through gender bias as well and lost a lot of my original personality which I've only just started to reclaim back through a lot of the molding that happens as a graduate as an example early days I used to get a lot of feedback from my peers that I'm very upfront very brash or sometimes bordering on rude and I need to like calm the hell down and soften my language soften things right And I think reflecting back on it this is where the truth and the reality you know the truth is somewhere in between two worlds and I don't know where exactly it is but I'm pretty sure some of it was gender bias and some of it was probably yeah maybe I did I was rude a couple times sure and so all of that I'm slowly starting to reclaim a bit back in the way starting to you know especially in the last few years starting to be more confident more you know sure of everything of my views but I've also learned how to present them in a way where they're strong opinions but loosely held you know the language to frame that where I'm totally open to feedback where we could definitely go in a different direction but here's a strong opinion to start with
Laura Nicol: knowing what you know today and using that as an example would you do anything differently or is it just being a learning journey that you've needed to go on
Ships Mahindra: I'm on a learning journey even today um know I'm still learning don't think you can ever stop learning And I'm still learning that actually these traits probably go back to the way I was nurtured brought up with my parents and their thoughts and beliefs and the foundations they laid some of it goes back to that too where girls are meant to be Quiet and closed and soft and bring in with the calm voice in the room and boys are meant to be loud and boisterous You know there's a lot of that societal norms playing here as well So I can't really say there's anything I could have done up front other than I think the only thing I could have done up front which I think I should have is just expose myself to even more experiences As a software engineer I stuck to one company for almost four years That was not right I should have jumped I should have had different career experiences and I should have different life experiences Just even travel whether it's taking that leap of faith and going on an overseas semester abroad during my bachelor's I should have done more of that
Laura Nicol: in your pursuit of finding yourself in a way of like how can I show up uniquely as me Has there been a great resource or a process that you've gone through that's helped you get there
Ships Mahindra: this goes back to the psychology of the way you think I've learned this in the last year only as a tool so it's very new and I'm still practicing it but very much Reflecting on what's a must or a should day to day simple example you want to be a good citizen of the world so you must pick up and clean up rubbish behind you that's a must And every time when I'm doing something recognizing those and Giving them that frame and then really understanding is that really a month or is that something I was told but there are other options out there and other ways of living that haven't explored yet there's a foundation that's laid for you early in life And it's almost questioning every brick of that foundation is that the right brick Do I still want that there Or no I you know that's something I don't believe in anymore and okay so then what is the new thing that I believe in I don't know
Laura Nicol: Totally It's that topic of belief systems I love it And thank you sharing so vulnerably we're going to look ahead to the future now and I'd love to hear your perspective on what the future of work will look like for tech operators
Ships Mahindra: one of the things that I've started to realize over the last year and I know it's again probably cliched but I do feel like AI will change a lot of the ways of working I'm not sure if it will be in a good way or a bad way because as we become more and and more reliant on AI do things to get things done like writing a product one pager for example even had GPT can do that but not very good but there are better elements out there already that can do that much better and so we're starting to outsource a lot of the doing of our work to AI But I have this fear ultimately and this is where I feel like I'm a bit of a pessimist and all of this Lots of people see AI as this accelerator I think it could only be an accelerator if you know what you're doing like you've been through the pain yourself You've written 101 pages before so you know exactly what it's used for what the patterns are how best to leverage it if you've never done one before and you're a new graduate and you're still learning it But then you start using these tools you don't know what good looks like So you don't actually know what you're producing right So this is where I feel like it will actually make us dumber in a way
Laura Nicol: You're like get into that scale up get that experience
Ships Mahindra: Yeah so for me I think the future is going to be people who understand how to do things manually and at the same time can then leverage the technology to accelerate themselves the people who'd win and who do well
Laura Nicol: I very much agree where do you reckon the Australia New Zealand ecosystem is heading
Ships Mahindra: if things play out politically the way they are we're going to be doing really well in the way that we'll become one of the next top five innovation hubs If Like I said if policies and stuff play out the way they do we definitely have the potential of being in the world's top five innovation hubs and in a positive way So we're going to be the hub as you probably know New Zealand and Australia may be less so but New Zealand's very much thinking about sustainability getting the planet into a better shape doing their fair share towards the U N Goals that have been laid out and because of that we are very uniquely positioned to bring out innovation in that space yeah I think we can win that space in the long run
Laura Nicol: if you had to name another operator doing incredible things in our ecosystem or abroad who would you name
Ships Mahindra: I'd like to give a shout out to Colin my current VP of product at Octopus he's been fantastic and sort of foundational in terms of building everything at Octopus engineering culture product culture design culture all of the good things the ingredients the magic ingredients that come together to build an awesome product yeah he's been really great
Laura Nicol: The glue of the culture as well it sounds like
Ships Mahindra: Yeah very much so very much defining the way we work at Octopus and what things are important how to make Octomus a place where people can feel that they do their best work
Laura Nicol: Well here's to you Colin we are getting to our last segment which is a brand new segment for the podcast inspired by my last guest Harry Uffendell it's a quickfire round Let's get stuck in who's a leader you're aspiring to be like
Ships Mahindra: my ish
Laura Nicol: Yeah he's made this interview prep a delight too coolest way you've used AI recently
Ships Mahindra: Oh I discovered this new tool granola actually I lie Lenny discovered it in his newsletter or whatever posted it And then I stole it off that but it's amazing It makes all of my meetings really really easy because it summarizes all the action items and the key points that were discussed love it
Laura Nicol: and it's accurate
Ships Mahindra: It's accurate It's actually accurate and you wouldn't believe it but obviously in the industry of DevOps we have highly special technical terms that are only relevant to our industry And it picks up all of that too very clearly
Laura Nicol: Amazing So one skill every operator should master and why
Ships Mahindra: Learning from others learning from others more importantly outside of your company outside of the current comfort zone that you're in find a way to connect network and then learn from the best in your field Locally or internationally
Laura Nicol: The biggest misconception about your role
Ships Mahindra: Oh that I get to own the decisions Yeah as a product manager you never get to own the decisions very rarely do you get to do that You're the one shaping the decision and then everyone gets to stay in them
Laura Nicol: The one resource you swear by and why
Ships Mahindra: because you've given me a reference there more recently one of my favorite frameworks has become a Rose Bud and Thorn conversation don't know if you've heard of it but it's about something positive that happened which is a rose something you're looking forward to is starting new is a bud and then thorn is what's a blocker or roadmap or something prickly and I use that for almost everything now somehow it's deep into all my conversations where Even if I'm having a one-on-one I'm like okay what's your rose bottom tone And this can be about your life right What's happening in your life and then for team meetings and retrospectives is obviously a well-known tool but it's just a great tool to just get to know the other person in a corporate setting And yeah just keep reaching out for it more and more
Laura Nicol: A piece of advice you've received that you'd love to pay forward
Ships Mahindra: I've received this advice through multiple people now and it's about confidently making mistakes Continue to confidently make more mistakes so you keep learning more and more and what that means is you know plan for a mistake to happen in a way It's just like yep I'm going to go make this decision or choose to do this action but it could totally be a mistake Be prepared for that and plan for it and have other options ready and learn from it continue to always confidently make mistakes
Laura Nicol: hardest decision you've ever had to make as an operator
Ships Mahindra: when I was working on the mobile stuff at Canva we chose to stop developing the mobile apps in their native languages in the iOS specific and Android specific languages And we decided to then move that into a single code base So it should be the same code run across web and mobile And that was really hard on multiple fronts it was against best practice firstly Secondly it meant a lot of the folks the engineers working on it won't have the roles that they were in even from a user experience perspective and the longer term direction it was just very dicey whether we you know we were very unsure if the experience would be as good and so we did do a few spikes and we ran a few experiments and tried to attack smaller pieces of the mobile app to experiment with this so this was now after my time so by the time I'd left Canva it was all working out It worked out pretty well actually for them It was just hard at that time because it affected people's roles and what they'd be working on mainly
Laura Nicol: Very powerful thank you And then who's an operator I should have on the show next
Ships Mahindra: Oh you should get Cullinan
Laura Nicol: Ah Colin
Ships Mahindra: Yes
Laura Nicol: from me
a final question I always ask every guest is what's a tactic or piece of advice that's helped you stay grounded
Ships Mahindra: I think my family helps me keep grounded really They're the bedrock of my life and whether it's support from my husband or my mom or just playing with my son and learning How the world works from his perspective you know all of those things are really powerful that's keeps me grounded in terms of not losing my identity completely to my work
Laura Nicol: there's something so special about the perspectives in the mind of a six year old
Ships Mahindra: Yes there's like things that they ask about that I've never thought of and never questioned So it's almost like rediscovering the world from a different perspective
Laura Nicol: this is the perfect place to end the podcast Thank you so much for your time today and I'd love to know where people can find you
Ships Mahindra: LinkedIn would be the best way to connect with me