Q&A with Audrey Cheng, CTO @ Imagr

We caught up with Audrey Cheng, CTO at Imagr to learn more about her winding career path into tech, what the role of CTO looks like on a day-to-day basis, as well as a look into some of the lessons she has learnt along her journey to becoming a CTO.

Audrey was kind enough to share some guidance on what has helped her progress in her career, how she has worked hard to get better at public speaking and storytelling over time and why she is so excited about joining Imagr.

About the Speaker


Audrey Cheng

Audrey Cheng is the CTO at Imagr

Transcription of the Q&A with Audrey

“I'm really new. So if we don't count the weekends, I think it's day seven or day eight, I think.”

Greg Denton:

All right, welcome everyone. Today, we are having a chat with Audrey Cheng CTO at Imagr. Audrey, great to have you on. First things first, if we could get a quick background as to who you are and what you do.

Audrey Cheng:

Hi, Greg. Thanks so much for having me on. Great to be here with you. Well, as you mentioned, I'm the CTO at Imagr. And so at Imagr, we really help support retailers provide a really frictionless shopping and checkout experience for their shoppers and that's really through our computer vision technology.

Greg Denton:

Outstanding. Now, you are feeling new to Imagr yourself. How many days have you been?

Audrey Cheng:

Yeah, I'm really new. So if we don't count the weekends, I think it's day seven or day eight, I think.

“..soon find that the workload never decreases, it's constantly like this. So you really have to challenge the way that you are working.”

Greg Denton:

We'll get into that a little bit more in a moment, but first we'd love to hear a bit more about your background, Audrey. So can you give us a quick snapshot as to your career journey leading up to becoming a CTO?

Audrey Cheng:

Yeah, absolutely. Well, most recently I was the Chief Product Officer at a company called SnapComms and we've really focused on employee engagement. We had a communication tool that really helped to help employers really engage their employees.

Particularly, in this time when we're working in different, like working from our homes, working in different geographies. We're more distributed and SnapComms was acquired by a company called Everbridge who focuses on critical event management systems.

They've got a ton of products in their suite and they focus, on as I said, critical event management system. So we think about the tsunami warnings that we've had here in New Zealand, the earthquake warnings, and you've sort of seen your phone shake with an alert. That's the Everbridge system.

It was a really interesting experience. I had the opportunity to lead the Auckland team in partnership with Phil Nun, as well as lead the Global UX team as well, across all products. So that was a really exciting time for me, leading the team, learning so many different products and really leading a wonderful team.

Prior to that, I was at Pushpay and I was the VP of product there. I was there for six years. Pushpay is a hyper-growth company. So really leading and growing that team from the beginning, which was a really exciting opportunity and really lots of lessons to learn about yourself and about the challenges that companies face at a really fast pace.

I think the most important lesson is really about your own growth and about the growth of the people around you.

It is really challenging what your idea of success looks like. I remember a time there really thinking, "Oh, there's lots to do. So I'll just work a little bit longer. I'll work a little bit more."

But you soon find that the workload never decreases, it's constantly like this. So you really have to challenge the way that you are working, the way you think about work and what you prioritise. That was a really interesting experience.

I've been in technology for a long time, I guess, more than 15 years. My first real job out of university was at Auckland Hospital at the medical lab there. I've had a really diverse and interesting career and product management wasn't something that I was thinking about.

It was actually something I fell into. I think when we think about careers and backgrounds, sometimes not everybody knows what they want to do. I think having that rich diverse background really can add to a role rather than take away from having a long, lengthy service in a particular profession.

“..my hope really is to create a really great high performing team with a strong culture of care and empathy for each other while also striving to hit those strong goals.”

Greg Denton:

Yeah, that's super interesting. And then I suppose, coming from the product side to being a CTO, could you give us a top line sort of description as to what are the core objectives of a CTO?

I know that will be different depending on the organisation and you're probably still figuring that out, but what are those three main objectives or what is the day in the life of a CTO at Imagr?

Audrey Cheng:

Yeah, absolutely. I think, for me, the role is really about helping the organisation to think about their long term product and technology strategy, right? And a lot of that has to do with the amazing work that the team is already doing.

You know, communicating that, understanding what the market looks like, and making sure that we really have a really strong line view from what the market needs are, where the customers are, where they're going and making sure that we really can help and attack those challenges from the technology perspective.

And so a lot of my role is making sure that one, we are aligned across the board in terms of the organisation on helping our retailers.

Secondly, is really helping make sure that we hit our business objectives so that we can grow as our retailers grow and really so that our team underneath, as well, can also grow in their career and their profession by achieving some really amazing things through the products that we're building.

And so my hope really is to create a really great high performing team with a strong culture of care and empathy for each other while also striving to hit those strong goals.

“..I think I was really hard on myself for not having it all figured out in my early twenties and I think like you think you're supposed to know it all at that point”

Greg Denton:

Is there anything that sticks out from a career standpoint that you wish you would have known earlier? Or if you were say talking to a younger version of yourself, do you have any advice for that person?

Audrey Cheng:

I don't know if I have advice, but I think perhaps earlier in my career, I was really hard on myself by not knowing what I wanted to do. You know, I studied... I have a bachelor of science. I thought I'd go into medicine.

I obviously didn't take that pathway, but I think I was really hard on myself for not having it all figured out in my early twenties and I think like you think you're supposed to know it all at that point.

I think you're really hard on yourself sometimes when you feel like, "Oh, everybody's becoming an accountant or a lawyer, or they've gone down an engineering path or they've chosen a particular profession."

But for me, I really didn't know what I wanted to do. I was just really interested in a lot of things, you know?

Someone would say, "Oh, hey, I've got this job over here. It's in finance." I was like, "Okay, let me give it a try." I think at the time I felt like, "Oh, do I have this wandering career?"

But to be honest, I think a lot of the roles that I had in the past really helped to give me a different perspective in many different ways, and I think that has been really helpful in my career as a product manager now.

Being able to put myself in other people's shoes to understand what it's like to be in sales. What it's like actually to be in customer support where customers need help now and they're really stressed out. Understanding what the pressures feel like.

The decisions that we make in the product today, how do they actually impact our teams? How do they impact customers? How do they impact if you're selling to a business, how does it impact their downstream customer as well?

I think having that rich background now as I look at it means that I'm able to think about different perspectives, and it's a little bit easier for me to bring that experience to the table, and to be able to consider different perspectives as I make decisions in our technology.

“..trying different things and being open to different opportunities and taking things that might have been slightly outside of what you were thinking is often a great opportunity to explore..”

Greg Denton:

Do you think you see that quite often today as young people putting too much pressure on themselves to have things figured out too early?

Audrey Cheng:

Oh, I think people do it in general. I've seen it all throughout. I think it's just the way we are. We feel like we're supposed to be successful out of the gate, and I think we're supposed to know it all, and we're on a pathway, and we should be really intentional about everything, but I think it's hard.

I think particularly early on in your career, you don't know what's available to you. You don't know all the roles that could be out there. You don't know how to really unlock your own potential.

But I think trying different things and being open to different opportunities and taking things that might have been slightly outside of what you were thinking is often a great opportunity to explore and learn your own talents and interests and build skills.

Greg Denton:

Yeah. And sometimes you gotta figure out what you don't like, as well.

Audrey Cheng:

Yeah, absolutely.

“I've seen people really accelerate their careers by letting their managers know and getting support from their managers to help them provide opportunities.”

Greg Denton:

When we first caught up, Audrey, you were talking about that early stage of your own career in terms of actually just owning your own professional development.

Can you tell us a little bit more about your own personal experience of that, and how that sort of helped shape your career journey into becoming a senior leader within a really interesting business?

Audrey Cheng:

I think, to be honest, for a long time, I found it very hard to find a pathway. And then I thought, "Oh, I'll take a little bit more generic pathway, maybe trying to go into project management or business analysis."

I think there comes a point where you realise that actually people are around, and you're hoping that someone is going to give you that "Aha!" moment but I think taking those opportunities and opening your own eyes to what you enjoy doing, what you don't enjoy doing, and then trying to, even if you don't know what careers those are even just saying like, "Hey, I really enjoy doing things like this."

Trying to write down things are you are really good at, and then trying to find things that actually are in that vein. I think once you are in a profession that you do enjoy, quite often what I see with team members that I am supporting is that they're expecting me to tell them what their career path should be.

Quite often that's not really possible cause I don't know what they enjoy doing. I don't know all the attributes, but if they can kind of narrow down the things that they like doing, what they like doing, what opportunities they might like to try or what projects they might like to try, then it's a lot more helpful for me in terms of trying to find a match for them.

I always try to find opportunities that help people stretch and grow, but I can't do that unless someone says like, "Hey, I'm really interested in learning about this. I don't really know much about it, but if there's an opportunity, I would love to jump on it."

That is much more empowering for the person, than taking control of their own career and helping direct where they might go next, rather than me going, "I have this work, I have this project. I need to give it to somebody."

If I can find a match between what I've got and someone that really wants to learn that I'd really love to bring those things together. And quite often what you can see is people begin to flourish and then their eyes open a little bit more and they're like, "Oh, well next I'd really like to try this thing."

I've seen people really accelerate their careers by letting their managers know and getting support from their managers to help them provide opportunities. Of course, you got to put in the work, but if you have a supportive manager and you're very clear about what you want to learn, I think that you'll find that you'll get a lot more support that way.

“..even coming and speaking today, I still have a little bit of anxiety about doing that and I think it's been a journey that I've been on..”

Greg Denton:

That's really good advice. I suppose being the captain of your own ship and really taking ownership of your career is great advice.

In terms of breaking that down into more practical steps, for you, have there been any examples of you sort of coming to that point of realizing that you needed to take more ownership of your own personal growth?

Audrey Cheng:

Yeah, I think as you progress in your career there are skills that you think you have, but that perhaps are not as sharp as you think that they are.

And one of the areas I think for me that has been an area of focus, actually, for the last six years has been around public speaking and storytelling. It's really not been an area that is actually comfortable for me at all.

And even coming and speaking today, I still have a little bit of anxiety about doing that and I think it's been a journey that I've been on and to be honest, I'm really grateful that someone had the honesty to tell me that actually, I was not a very good public speaker.

To give you an example about that is I used to stand up, and even in my small team, I have my notes, be really shaky, and then read my notes, and that's not a very engaging way. I've been really trying to one, build the confidence to be up there.

One of the things that really helped me was someone said to me, "Well, Audrey, your perspective and your experience is really uniquely yours." No one can tell you that's right or wrong. And that really helped me a lot because I think it's that idea of standing up there and people judging your ideas or what you say.

I think that can be often really hard for people, particularly like you're standing up there, you're very vulnerable. So for me, what that pathway looked like was being really intentional about that learning and doing it for six years.

The first step really for me was getting more and more comfortable in front of the team that I was working with, who are really supportive. Starting to do one external talk where there were people I didn't know.

I started out with a panel talk, which is a little bit safer. I asked for the questions in advance. You're in a panel of people who are going to swoop in if you are stuck.

Slowly building up to bigger and bigger talks and finally being able to do a large public talk whether that's in person, I was able to do talk in Melbourne, in person at a conference, being able to do digital talk to 2000 people. All of these things take time to build up.

I still feel a lot of anxiety when I'm doing them, but I think small steps incrementally and the things I did along the way were things like Speechcraft. At Pushpay, we had a really great team of people who had listened to your talk before you actually gave it, whether it was internal or external, and that was really supportive.

Having people there who would be honest with you and help you to grow in your journey.

And they weren't all managers that were helping me. They were engineers that were participating in the Speechcraft program, who would give me feedback on my talk and give me some tips on what they thought I could do better.

That was really great. It's a really great way to build team comradery around it. You support them, they support you, and then slowly build-up.

Now, I'm really sharpening the storytelling element of my public speaking. It is really to try and be a more engaging speaker, trying to get better at bringing in external stories that people can relate to. It's still a journey. I'm not done yet, I guess.

“I think sometimes it's really hard to give feedback and I think that's something that we all need to learn. ”

Greg Denton:

Yeah. It seems like you seem extremely confident when you're speaking. It's surprising to hear that it's been such an area of focus, and obviously the work that you've put in is yielding dividends.

In terms of that first part that you mentioned, in terms of people actually highlighting to you that perhaps it wasn't one of your strongest skill sets, was that a close friend or a colleague? Because that's quite a confronting and brave thing for them to do.

Audrey Cheng:

Yeah, it was someone that was like that I worked with, was my manager, but someone also that I have a lot of respect for, as well, and a friend. I think sometimes it's really hard to give feedback and I think that's something that we all need to learn.

That skill actually is how to give feedback and how to receive it. I think I'm a really big fan of radical candour. I think the elements of radical candour are really positive. It's about being direct, but also delivering feedback with humanity and making sure that the timing of the feedback that you're giving the person is open to it.

If I'm having a really bad day, probably a really bad day to give me feedback. If I'm doing all right today, and you can always check in about it, I think maybe it's a good day to give me some constructive feedback, but it's good for people.

And I think people really crave some feedback because feedback is a gift. If it's given with the right intention, it helps you to grow. It helps you to see those blind spots in the way that you are delivering things, in the way that you're working, things that actually help you to be more intentional to focus on.

I think I always say about feedback if you don't have to act on every feedback. Feedback is a gift, so you choose to receive it or you choose to receive it and say like, "Hey, that's great, but I don't really think that's something that I want to change or I want to do or want to focus on," and you can leave that, and it's okay.

But I think it's great to be open to hearing feedback and to listening because what one person perceives may also be what another person is perceiving as well about your actions or what you're doing.

“..is this a way to actually get people of backgrounds of diverse thinking into our organisation?”

Greg Denton:

Yeah. In terms of that first point is people actually going out and being really intentional about seeking honest feedback to find out their weaknesses. And then I suppose the next part that you mentioned is that you had a lot of support around people actually continuing to give you feedback, to make sure that you progressed.

Who were those people that really stood out in your sort of journey? Was it, as you said, not always your managers, it was people that were also trying to upskill themselves, but were you quite clear as to the people that you were regularly getting feedback from to continue on that journey?

Audrey Cheng:

I think I would ask, I asked a lot of people. We had a group of like people who took speech craft that would participate and it was really great when people want to participate in a community like that, and I felt that was really wonderful, being able to have an opportunity to present in a safe space and equally to share and give feedback as well.

I thought that was really fantastic. Quite often I will ask people who are open to often giving me feedback, "How do you think that went? What do you think?" And sometimes I'd say, "Oh, it was good. Next time try and be more spontaneous in the moment. Maybe incorporate what someone said in the previous talk into what you're doing."

I think when you are open to allowing yourself to not be perfect at having always perfect delivery, then you really open yourself up to grow and to take on board feedback to be better next time.

Greg Denton:

Yeah. That's really interesting. I think that so many people share that same fear of public speaking. I think for of people like yourself to share that has been a bit of a journey to continue to get better at it, and, I suppose, keep working at it's.

I think it's really helpful for others that might be starting out at an earlier stage, trying to get better themselves. Switching gears a little bit, Audrey, we obviously, a couple of days ago had International Women's Day.

In New Zealand, we still have a really long way to go, particularly in terms of getting more women participating in the industry and not just participating, but helping lead these organisations. As someone that has a really good influence at a senior level within a tech company.

What do you think we can be doing more of in New Zealand to encourage not just greater diversity in terms of gender, but right across the board?

Audrey Cheng:

Yeah, well, definitely, I would love to see more diversity at senior levels and I think part of that is for all of us to be thinking about the environment that we're creating within the workplace and what those expectations are, and are those welcoming to the people that we want to be part of the organisation?

I think that's something for all organisations to think about and reflect on like, do our processes allow for different people to come on board? We design these processes, so they're a little bit biassed towards the way that we work and how we judge things.

I think opening ourselves up to think about, "Hey, is this a way to actually get people of backgrounds of diverse thinking into our organisation? Or do we have a cookie cutter process that we're always going to get the same type of people through our organisation?"

Audrey Cheng:

And I think that there are some things that we need to be thinking about in terms of reviewing those processes to see like, "Hey, how do we encourage more people?" I definitely think seeing more people in an organisation also is very encouraging.

I think organisations need to be thinking about how to do... As we think about these processes, it can only get better if you can attract more people into your organisation. I think thinking about it too late means that you have a lot of heavy lifting to do.

One of the things I think is really hard is that I think often women are the ones that have to, or people of diverse backgrounds end up being the ones trying to drive the change.

And I think that there are a lot of allies out there, but maybe not knowing how to support in the right way.

I think on both sides, we have to be open to teaching people how to think about the challenge of creating an environment that's more welcoming to a wider group of people, thinking about how we think about talent, how we think about... If we think about a traditional talent pool is, go to university, you study, you come into the industry.

We have to be thinking about the world that we have, now. We have a lot of people who have been displaced out of their own industry. People who are rethinking their lives and thinking like, "Ah, this is a chance for a new career."

I think we as an industry also have to be embracing of that and thinking about how do we help people transition into the technology industry?

We know we have a shortage of... Or you have a skill gap here. We know we have a shortage of people for the technology industry, so we need to be thinking creatively of how we bring onboard people in the industry, whether that's out of university or whether that's later on in their careers.

I think this is the time for reinventing yourself, trying something new and getting out there. I think the tech industry can create amazing career paths for people. I think it's an amazing industry to be part of.

“I don't have an engineering background myself, but for me, I really love technology and I really love how it can help people on a scale”

Greg Denton:

That's interesting. I suppose to that point, I think there's often a perception that working for a tech company or in a startup you had to have been coding as a teenager or you had to have some real passion for the technical side of the business.

Whereas you're an example that is not necessarily the case and there are many others in terms of that as well. Were you ever, when you were studying a bachelor of science once upon a time, ever thinking about working at a really cutting edge hardware/software technology company?

Audrey Cheng:

No, I definitely don't... I don't know that I thought in those early days that I would be working in technology let alone leading a technology team.

Yeah. I think even for me, I feel like at some point I started a new... I started down this technology career path but it wasn't something that I was sort of thinking about in those early days.

It's amazing. I think that technology has brought about access, right? It's brought about access to education. I think that today people do a lot of self-learning, transition careers. I've seen people go from IT networking to becoming a software engineer.

We've seen software engineers become product managers. I think product management is actually a really interesting and great example actually for what we're talking about.

I don't have an engineering background myself, but for me, I really love technology and I really love how it can help people on a scale and those are the things... I'm a really curious person.

I really like knowing how things are made. I really like solving and helping people. I think that what technology can bring is helping people on a larger scale. I think there are lots of careers within technology where you don't have to have come from an engineering background, but you have to have that curiosity.

You have to have that mind of thinking about how to bring things together, but there are a lot of creative careers as well within the industry. If you think about product marketing, it kind of brings the marketing and the technical marketing skill sets, the creative marketing skill sets and brings that together into product development.

We partner really strongly with product marketing because we want to make sure that our message is resonating strongly with our market. That's how we make sure our products are successful for example, as well.

I think there are a lot of careers that can comment that are part of the technology industry where you don't necessarily need to be, or have come from an engineering background.

“I really think that people who are self-starters, take the initiative, are curious, willing to learn. ”

Greg Denton:

There's not necessarily a typical background. What do you see as some of the key traits or characteristics of people that typically do well within startups or the tech environment, given that you've been exposed to a lot of people that have worked in that industry?

You mentioned curiosity and you mentioned an aspect of self-learning, but what are some of the other things that you see that are common?

Audrey Cheng:

Yeah. Well, I think curiosity is a big one and I think problem-solving is another one that I would say, so that curiosity is like, "Ooh, this is interesting," but then also like, "Ah, how might we solve it?"

I think is also another interesting element, I think for startups, really, people who... Kind of going back to the growth mindset, people who are self-starters. We don't all know everything. Sometimes we're doing this for the first time.

Even having been in the startup world, new problems or challenges come up all the time. It's the way that we attack those and go and learn so that we can have that, "How might we solve" moment.

I really think that people who are self-starters, take the initiative, are curious, willing to learn. I think more strongly it's becoming more valued, it's being able to build empathy and have empathy for others. We build products for people. We're not building technology for technology.

We're building things to help people. I think when we put people at the centre of what we're doing, it's so much more powerful than saying, "Hey, this is so cool, it's leading-edge technology. Who cares about the consequences?"

Audrey Cheng:

I think having that thought of like, "Hey, what do we create and how does this help someone else? How does it change the behaviour? How does it make someone's life better?" That and also thinking through like, "Hey, how does this affect my team? If I descope this, how does it actually influence my customer success team?

How will this affect our sales team? What are they going to encounter? What are they going to face?" Building empathy also for your teammates I think is something that's really important. I don't know. Those are the qualities I think I value in people. There are some very specific skills that you need for each of the roles, but, in general, those are the qualities that I value.

Greg Denton:

A lot of the advice seems to come from a very good foundation in product management. Would that be fair?

Audrey Cheng:

I'd say that's fair.

“..this is a really great team, really capable and we could really do something amazing together.

Greg Denton:

Switching gears a little bit, in terms of your perspective on Imagr, given you're coming at it with a fresh set of eyes, obviously an incredible company that's really revolutionising the way that people think about shopping and that's both hardware and software, what was it that, I suppose, initially attracted you to the business in the first place?

Audrey Cheng:

Yeah, I think there are so many things. I actually had talked to Will a few years ago, but I think the timing just wasn't quite right for us. I think the problem is actually a problem that I've been thinking about even in my own personal life, that the problem that we're trying to solve, really, for shoppers and retailers.

I feel like this industry is ripe for disruption. The same user journey my mom had when I was a kid is the same user journey that I have today, more or less.

I have had those instances where I've been rushing. My kids are still young. A few years ago I was still picking them up from daycare, and then you're thinking about the meal that you're going to put on the table and you quickly run to the shop.

You pick everything you need, you go to the checkout and you're like, "Ugh, I don't have time. Daycare's closing in 15 minutes." You leave your basket, you walk out of the shop, you go get your children, and then you're like, "Okay, what do I got in the pantry?" That idea of the fact that like my mom has the same journey that she had all her life and I now have that journey. I feel like this could be better.

We are probably busier now because of technology and the internet and the access to information, and, I guess, just the pace that we're working at now and so the demands on our time are greater.

I think that we can help retailers really support their shoppers and give them back time, giving them a really great experience so that they can go on and do the things that they need to do with their families and in their lives. I really love that.

I think technology is really interesting, too. I think it's a really interesting space to be in with the AI and computer vision pieces, how we might leverage that technology to support improving people's lives.

I think it's a really cool space to be in. I just really love the team. Meeting with all of the team members, I thought, "Ah, this is a really great team, really capable and we could really do something amazing together."

Greg Denton:

That's really interesting to hear. I suppose it might be a bit of an unfair question given that you are in the early stage of working there, but what is the current state of play?

I know obviously deployments in Japan, deployments in Europe, and really starting to be held in the same conversation as Amazon in a lot of ways, in terms of disrupting that shopping experience. What is the current state of play at Imagr in terms of the markets that you're operating in and the state of the product?

Audrey Cheng:

I think right now we have Japan, and we have the focus on Europe. I think for us, we're really wanting to build momentum, show that the journey can be different, demonstrate that. I think retailers are really receptive to and open to the solution and a possible different journey that we could be supporting them with.

I think it's a really exciting time for retailers. I think regardless of people still do shopping online. I think people all still go to the shops. I still go to the shop. I do online shopping, but inevitably I find myself there.

I think providing that really great experience when you are on-premise is a really amazing thing for retailers to be able to provide to their shoppers. I think we're excited to be able to be there at Imagr.

“ We have a lot to accomplish, a lot of amazing challenges for really talented people to come on board and be a part of.”

Greg Denton:

That's cool. And then finally, before we let you get back to your day, two-part question. The first part is why do you think now is such an exciting time to be involved in startups or involved in tech in New Zealand and why should more people be considering it? And then secondly to that, is why now for Imagr?

Audrey Cheng:

Well, I think there are so many exciting things going on. New Zealand's amazing for building tech talent and for us at Imagr, I think we're at the beginning of our journey. We still have a lot to do. We have a lot to accomplish, a lot of amazing challenges for really talented people to come on board and be a part of.

We're really excited about where the market is going, what we can achieve for our retailers. I think this is just a really great time in the business to grow and I mean, I'm sold.

Greg Denton:

Perfect. Well, we really appreciate you taking the time, Audrey. I found that super interesting hearing more about your journey. It's obviously an incredibly exciting time to be part of the Imagr journey and we are looking forward to hearing a lot more from yourself as well as the rest of the Imagr team, so thanks for taking the time.

Audrey Cheng:

Great, thanks so much, Greg.

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