Jackie Newnam is a tech savvy professional with high aspirations in product strategy, product marketing, and scalable process. A Butler University grad with over 15 years of experience living overseas, her international exposure in Southeast Asia have prepared her to be highly adaptable in different environments and build relationships with a vast majority of personalities and cultures. A master of roadmapping, Jackie isn't afraid to go off-piste and tackle big problems by breaking.

 Max: Hi, Jackie Newman. How are you?

Jackie: Hello. Good. How are you?

Max: I'm very good. Thank you very much for making the time and being on the show. 

Jackie: Absolutely.

Max: Very excited with you and talk about all things product, working, asynchronous communication; all these buzzwords. To start, I would just love to hear about you. This is something I don't know. If you could take me through your career and product and how you ended up in the position you are now

Jackie: Yeah so now I'm at a senior product management level, which is crazy. I started in sales in lead generation and then quickly realized that my colleagues were getting more leads than I was, which then brought me into marketing operations, and then I quickly moved into product operations overall. So then that eventually led to the decision of whether I wanted to go into product marketing or product management, and I found that I really enjoyed working with developers, putting a plan together, working with design, less copy person, more of like design-oriented. So quickly started into product management through being a product analyst to begin with, which I think is really important in this day and age with data. Big data, the big buzzword, but then moved into product management, was specialized in enterprise product management for a long time at a forms company called Formstack, and then moved over to Typeform to become a product manager specialized in distribution, so how do, people get access to forms in the channels that they're in. Then I moved to Process Suite to be a product manager here focusing on many different things based on the stage of this startup. So I think having different experience in different size product orgs and where they are in the life stages of a product has been really, really interesting and eye-opening, especially at this new startup that's a lot smaller than I'd been at.

Max: Okay, interesting. So how many people are at the Process Street at the moment?

Jackie: I think we have 80, like 75, 80? And we've got about - I just looked this morning - just over 5K customers, but then we've got 700,000 users of different aspects. So you got creators and then you also have users, and we always have to keep these individuals in mind when we're building product.

Max: That's so exciting. So when you joined Typeform, it was kind of at that kicking off stage where I think it was maybe about 200 employees when you joined, and then it was more like 400 when you left...

Yeah it was around that, and it felt like more of like a stabilized product. We knew what we wanted to do and the things that we needed to do moving forward, and now it's more of, here are the things that our customers really need, and then we're up against innovation. So it's an interesting space to be in at Process Street and it's similar to forms where it is data collection, but it is more focused on automating process, making it fun, fast, and faultless for everyone kind of thing.

Max: Yes when I was looking into Process Street before this conversation, I was quite interested and was like oh cool! One of the main conversations I've had with people are about remote work especially, and I think a lot of what's kills company culture is  processes, and the sea of processes that are made that are also necessary because you don't have the same tools you have working together physically. So processes need to be in place. So how do you try and make processes cool? And I guess that's kind of what Process Street is doing. 

It started off as a checklist and then they quickly moved into more conditional logic, more automations, and then now we're getting into more custom customization of your brand. So you can have cover images across the experience to kind of give, like if it's a PTO request form, like having a beach to set the tone of what you're about to be filling out. We've got this cool new feature that I'm actually testing today where you can change the colours of the in-app experience to be your single brand colour. So trying to add as much splash of fun as we can, because processes can get boring. I would say that our specialty is employee onboarding and client onboarding. It's really where our bread and butter is, and onboarding through Process Street was really helpful to see your task list and then all of the different things that you needed to learn on another panel. It really helped organize me as I was learning the product and onboarding, but just get to grips with how quickly I can get up to speed in the first three months.

Max: That's great. I was gonna ask you what your kind of main use case is with Process Street. I guess onboarding makes sense because you know that I've only onboarded onto one company remotely and it's a hard process because there are some obvious things, but then there's some things where you don't want to leave someone stranded. Because if someone's stranded in the office, you have your buddy, you can kind of keep an eye on them, right? But if someone's feeling a bit stranded and they're just in front of their desk at home, it can be a bit worrying. So I guess that's a sensitive subject.

Jackie: Yeah, and I think one of the key features that we released - I think it was over a year ago - was being able to add comments. So if you're stuck on a task or something, you can just tag somebody in a comment to help you out. Obviously you've got Slack and email and whatnot, but something within the tool itself to be able to help raise your hand on a specific task that doesn't make sense or who knows.

Max: I think that really resonates quite well with me, just because I feel something that I've really, really valued when things have gone well in onboarding, is when you are immediately thrust into collaboration. Because you can often feel like you are not ready to raise your hand. You're like, I probably need a few months under my belt before I can raise my hand, so it it's quite nice that you're empowering people to do that already. .

Jackie: Yeah. Well, with forms in general, I think taking those paper processes and then making them online is a jump forward into the remote space, and I feel like once everything happened with COVID, forms got more interesting because people needed a way to communicate and work together without being in the office. Then Process Street I feel has taken it to another sub-level. Forms SEC does have a workflow product so I feel like it's rumbling in the form space to have workflows and databases and so I think I data collection's an interesting space.

Max: Yeah I bet. I would love to hear a little bit more, do you feel like you still use that sales experience that you got at the start? Do you feel like that's still feeding into your job role?

Jackie: I feel like it has to. You've gotta be compelling to get things moved forward. You've gotta have real, not swag, but you have to have that confidence in trying to get others to see your side without being too pushy. So I think that's definitely come in quite a bit, Especially when at Typeform and having - love Kim - but he would always be like, well, why are we doing this? And it's like, it's up against the CEO, let's go!

Max: That's so interesting. Was it Formstack you were at before Typeform?

Jackie: Mm-hmm yeah

Max: And it was there you got various promotions that took you up to the level you are now as a senior product manager, right?

Jackie: Yeah

Max: So I would love to know what main lessons you learnt there and what kind of things you realize don't work and some things you realize do work and you've then taken onto your new jobs at Typeform and Process Street.

Jackie: Yeah, at Formstack in particular, it was not having a roadmap more than six months. I think at Formstack I was really trying to follow, I didn't necessarily have individuals that had done the role before. There was a lot of things going on, the head of product had left, I was kind of stranded and the first project I had was HIPAA compliance and releasing that. So that was a biggie and it was a lot of fun. It was a huge document I had to read, but I kind of doubled down on thinking about how we could create a roadmap that we could use for a year, and that wasn't realistic. Things change, customers have feedback, you need to pivot, you need to be agile, and it's just not worth the effort to put a year product roadmap together. So that was a big lesson there. I think another big lesson is product. You're like a parent, so you just need to make sure that everybody's getting along. You need to work really closely with design and because I like to say that product likes to squash dreams of what is realistic. And so working closely with design to make sure that you understand where they're coming from. They're designing the vision and helping them understand what is the happy medium of what is capable versus what is the vision. It's always good to show the vision to the developers, but then also making sure developers and designers are getting along because that's definitely a point of conflict that I've seen in other organizations that I've been at, and so making sure that everybody is getting along and creating an environment where everybody can have a collaborative approach, facilitating collaborative conversations and brainstorming. So I always like to think that - I think I had a manager at Typeform told me this - you and the engineering manager are like parents in this grand scheme of things, and so I think that was a big lesson learned there, where it was just like, we just need all get along so we can move faster.Being remote, it's so hard to get to know people, so at Formstack I had to forcefully create some of those environments so that we can all get to know each other, so that we can move fast and faultless without conflict. At Typeform it was the same because I think when I joined it was the first remote team of devs. Everyone had been in the office. Our office wasn't necessarily conducive to remote work at the time. I remember joining Zoom meetings and they couldn't figure out Zoom inside one of the conference rooms, and it was very challenging. Having developers come on board who have been used to a specific way of working, which is the traditional way of product or design, throwing a project over this gate and developers just going in and building it. So we wanted to create more of a collaborative approach, more of a Typeform environment as you would say, because we did have a really good culture. So facilitating a lot of those brainstorming activities really helped from my learnings at Formstack.

Max: Okay, great. I was gonna say, because you joined Typeform while there still was an office

Jackie: Mm-hmm.

Max: At the end of... was it the end of 2019?

Jackie: Yep. Yep. Bar-ception, lunch in the office. It was great.

Max: Yeah these things can't exist anymore, sadly. So yeah, you and I were in the same situation where I was at Typeform and I was in the office as well, so we both experienced the big change to remote. It's very interesting look at companies that start remote first and companies that become remote first, and how much harder it is for a company to change than just start out and choose it from the beginning, from the early stages anyway. 

Jackie: It's definitely difficult because at FormStack there was an office and there it was I think 30/70, 30% was in the office and then people were remote and there was perks that were happening in the office that everyone remote felt left out of. So that was really difficult. While at Typeform, everyone had to go remote. I think Typeform had a good way of facilitating remote work with Typecoins and benefits for everyone across different countries. So I think there was benefits there. Process Street is remote first, which is my first experience going into a remote company. Onboarding remotely, not meeting your friends or your colleagues until an office party or a meetup. So it has been an interesting experience and it does take a lot for organizations to change if they have not started remote first.

Max: How is that process now - like you say - you almost have to adapt this teacher role, this parent... How do you find that happening and managing to maintain that feeling remotely?

Jackie: Yeah, I think it's through happy hours and Friday dates where you're just chatting, talking about your weekend, talking about hobbies, playing games, but then also - and it's something that I had to start at Typeform, which was having brainstorming meetings using tools like Mural or Mural or now FigJam. Being able to start harnessing some of those brainstorming sessions online only. I've tried to do that at Process Street as well, especially with bigger projects that are coming up. We are working on a forms product, so that also needed a lot of brainstorming and discussion between developers and designers and ahead of taking it on as a project. So yeah, facilitating a lot of those conversations and just like scheduling them. I think that's the hardest part, is everyone's so busy and finding time on somebody's calendar for an hour or an hour and a half is challenging.

Max: Yeah, I think everyone feels the meeting fatigue and do you wanna say, even the Slack fatigue. I mean people love Slack, but you can get Slack fatigue quite easily because you're just kinda lost in channels and you're lost in notifications, not really knowing what notifications mean, and worrying that you're not gonna have the right amount in contact. So that was gonna be my next question, was asking what kind of tools you guys use at Process Street to keep your communication working and keep the product moving?

Jackie: We use Slack, but there is fatigue. There's definitely a lot of fatigue. There are channels that I pay attention to, channels that I ignore. I kind of have folders now with Slack like an alarm bell next to the ones that I know that needs my attention. I would prefer to have a balance between Slack and email. I think that's the space where if something that needs to be communicated this is set in stone. Something around communications about the company. I feel like email is a good space for that. Working with a team I think is better in Slack, but there's just a lot of discussion. And then I find that a lot of people would rather just communicate in Slack, and then it's like I'm spending more time reading and thinking before responding when we could have just had five minute discussion and that would've just solved it. So I think there's a balance of understanding of okay, we want everything to be in slack, but we also need to figure out what is more time consuming. Is it more time consuming for me to read your big ass paragraph and try and understand and internalize it? And before I respond, because you know, Slack is the word, you wanna make sure that you're being clear when you're communicating, especially via text. So I think it's always gonna be challenging in this remote environment. I think at FormStack the way that we really handled it was daily standups, which is also fatigue of itself, but it was a space to talk about problems that came up and to have a dedicated time to actually talk through them versus relying on Slack to communicate through text. We also use Loom quite a bit, which is video recordings of the pro-visual problem and then communication on top of that, which I think has really really helped me. It's not something that we did at Typeform as much, but at Process Street we're using Loom quite a bit and I think that really helps communicate on top of a paragraph of text.

Max: So partnering visual communication with text communication, I feel is probably what's gonna be helping a lot of teams, especially product and engineering teams in the future. It's because you need to be visual. It's like you said, it's so hard to explain things perfectly in a paragraph, and if you do, you end up with a big long paragraph. People see it and they're like, I'm not reading that now, I'm not gonna get exactly into that. Do you see in your experience, you think you're finding a tool that can actually visually show things better is maybe saving you time? 

Jackie: I think so. I think Loom is great. I think it, if there's a space where you can have a video and have comments - which Loom has - but it would be great to have more descriptive spaces. So if I'm asking a question, I can verbally show it, but then I can also type it out, specifically what I'm seeing as both and then having individuals comment. I think that would be helpful. I think the last follow up loop is for that comment to go into the main channel of communication which is Slack for us.

Max: Yeah, exactly that. I feel like what what slows down a lot of products and engineering teams is just the decision making part of it is is the feedback loop, right. That's one of the hardest things about asynchronous communication and the world of distributed work is you're kind of working on everybody's clock

Jackie: Mmm yeah.

Max: And not everybody's available at the same time, and definitely I think everyone feels a bit unsure of who makes the final decision. That's why it's very important to have those spaces work, like you say, where you can just make strong hard decisions.

Jackie: Yeah I think that's been the way that we work at Shape Up. The founders are really heavily involved and so I think the decision making line is very thin. At Typeform, it was product managers and I think that's helpful to have somebody that's gonna do the final, final decision. I feel like right now what I'm experiencing at Process Street is I'll make a decision and then someone will come in and be like, well, let's do this instead. And it's like, okay, that's great. Let's just do that instead. So I think every org is gonna be different.

Max: Exactly that, and there's no - this is one thing that's kind of been recurring across all the conversations we've had for the podcast - there's no quick fix. There's no one size fits all, and I think a lot of what comes down to being in the successful product team that actually pushes growth is just adapting, right? It's just adapting and adapting and adapting. 

Jackie: Yeah making a decision, iterating on it. I think the biggest thing that I've always tried to take is just not be scared to fail. Fail fast. If you can fail, fail fast as you can make a decision so that no one's bottlenecked. And if that was the wrong decision, well we'll fix it. It's not a big deal. 

Max: Exactly that. On the subject of working with the engineering teams, how are you doing that at Process Street? How are you kind of visualizing updates of the product and the changes you wanna be made?

Jackie: A lot of the time, every update that they are creating, they'll create a Loom video for us to watch, and then at some point we have feature flags in LaunchDarkly. So if it's at a point where it's pushed into that feature flag, we can test it on our own. We also have a testing environment that you can test on as well. I usually like to wait until it's on the feature flag because I know that there's nothing additionally being added at that moment. And so it's kind of like more of a final end product. So a lot of Looms and then testing on my own, and then I'll usually send a Loom back if there's any issues that I'm starting to see myself

Max: Cool that's great. And how are you finding going back to your original ideas that never make more than a six month roadmap? How is it going sticking to that ethos you've had?

Jackie: Well, at Processor we don't have a roadmap, so we work in Shape Up, which is really about taking what customers have been saying, what we've been learning about the industry and the market within the last two weeks and making a decision on what we wanna build. And so it's very fast paced. The developers have about six weeks to deliver something that is going to be put into the customers' hands. So it's like sprinting to the end. You're basically running this - I would say marathon, but it's really not, it's like a sprint - to get these lists of features that would help a customer with this specific pain point if some things don't get done, that's just the line that they build in. So I'll put a list together of the things that we wanna do. We've got designed for that list. Halfway through the sprint we'll figure out, we'll sprint halfway through the cycle, we'll figure out if all of these are accomplishable, they're in priority orders in chunks that would be valuable to customers so that if the development team doesn't get to a specific scope, it's not end all be all. We have the chunk that is going to be valuable to customers. So we don't have a roadmap. It is a little aggressive for the product team because we gotta pivot a lot. It's a lot of writing out new documentation and identifying new features or things that are pain points for customers and then putting what we call a pitch together. Basically a sales pitch of why that feature should be taken into consideration. Then that goes into a betting table with the director of product as well as the founders to identify what will be moving forward. And that's just kind of how we work.

Max: So you're kind of pitching it to each other constantly.

Jackie: Yeah!

Max: I feel like that could create a lot of ownership within the product. You feel like you really own a part of the product.

Jackie: At this stage of the org because we're so young and there's a lot of things that we've released that customers have additional features, requests associated with, it's a lot of everything. So I feel like I've not necessarily had ownership, it's more of ownership of pain points of customers and working on various different features associated with that.

Max: Okay, cool. Are you kind of prioritizing - I'm assuming you're still organizing this quarter by quarter, right?

Jackie: Yes.

Max: So do you go into a quarter and try to tackle a certain customer profile or are you trying to attack lots of different places at the same time?

Jackie: Right now we are focusing on employee onboarding in more of the enterprise space, which is where brand customization came in. Moving forward, I think we're gonna wanna focus on specific metrics and then have that as the theme of the cycle. I think right now the next cycle will probably be more focused on the drop off rate between signup and then actual creation of a workflow and focusing on not necessarily experiments, but features associated with moving that needle.

Max: That's really interesting. And like you were saying, you are about 80 people at the moment at Process Street, and you've worked with 5,000 customers and about 700,00 users. Do you find you are leaning on your customers more and more as time goes on, in terms getting that feedback and/or do you feel like you are able to make the decisions a bit more independently now?

Jackie: Now after a year and having a ton of customer calls, I feel like I can help speak for them, but I think we're still leaning on customers and how they're using us because I think in the past, everyone in the company was really focused on employee onboarding and recognizing that there are other different use cases that people are using Process Street for and making sure that we tap into those and understand their needs as well, I think will be key for us to move forward in being successful.

Max: Okay, great. That's really interesting. On that note, I would love to finish off the conversation by talking about the future of product and if there's anything you see in the product world, like any trends or any methodologies that you think are either, hey this isn't gonna be around in five years, or hey this thing we're doing now is gonna be the biggest thing in five years. What do you think is really gonna stick or not?

Jackie: Well, when talking to some of my colleagues around product, I feel like shape ups becoming more and more of a methodology that - I believe Basecamp was one that came up with it. And so I feel like a lot more orgs are adopting shape up in younger product spaces to help move quickly. I think there's always gonna be that challenge of how long things take, how quickly the estimate changes as soon as you get into the code. So I think it's really gonna depend on the org, how young their code is or how refreshed it is. I think more and more companies are going to be focusing on tech debt and making sure that their tech debt is handled or mitigated or there's a plan moving forward to constantly take that into consideration because in my experience, just having a ton of tech debt as at FormStack and at Typeform, it's very hindering to move forward and to move fast. So having that mindset of taking on tech debt and potentially moving into Shape Up, I think Agile will always be around. I think having plans depending on, where the product is in the stage of growth, like Process Suite is quite young and so there's still a lot of things that customers want us to improve on, features that we've already released. While at Typeform, it was more of a mature product where it was being innovative in finding new things to do and I think innovation, Agile kind of works more or Scrum works more with innovation when you're trying to focus on a new big thing that takes longer cycles to work on versus moving quickly on different items based on your customer's feedback. So I think it's really gonna be depending on the size of the company, the code bases, and where the product is in the growth process, whether it's a young product or a mature product.

Max: It's so interesting, isn't it? I've never worked in Shape Up. I think I've only worked in Agile. It sounds almost like a more agile version of Agile. It sounds like it's much more ready for spontaneity.

Jackie: Yes. It's a lot of pivoting and it's a lot of moving forward. I think it just depends. We take on shape up and we've made our own type of shape up methodology, and I think each organization's gonna take a bit of Agile or whatever and make it their own. If you're trying to move quickly and you're trying to try new things to see if they work or if you have a lot of customer feedback on particular items, Shape Up really gives you that space to be like, okay, what can we get? It's almost like Hive Sprint like at Typeform where it was like, what can we get done in two weeks. 

Max: Yeah lets kind of put ourselves in the box, right?

Jackie: Right!

Max: And put the constraints on to see if it inspires anything...

Jackie: And I feel like it does, because at that point, even with tasks, if you put five minutes down to clean your dishes, they're basically cleaned after five minutes. It's a mental space to be in, I don't know.

Max: It's very true. I think that's one of the things that kind of drives product teams so much is hey, we've got this crazy deadline and it's totally unrealistic and we're probably not gonna make it, but we're just gonna do our best to make it. And I think that's what drives the hey, how can we cut corners here without sacrificing the quality of the user experience? Or how can we make this process faster without having to hire another person. So I think it sounds like something I think a lot of people should try out, especially like you say, in those early stages.

Jackie: Yeah and I think the best way to have success is just having those milestones. Is milestone one something that's gonna be helpful for customers? I've seen in the past, milestones that don't really mean anything, and I think it's really important to make sure that they are not deliverable chunks, but something that's better than baseline, and having those milestones will really help move fast and get something out in the two weeks time or whatever timeframe you have.

Max: Perfect, cool. Thank you so much, Jackie! It's flown by.

Jackie: Yeah, I hope this was helpful.

Max: Yeah this is all so so useful. Thank you so much. If people want to hear more about you, follow you, where's the best place for them to do that?

Jackie: Probably LinkedIn. Yeah I'm not so much a Twitter gal. I don't know why but..

Max: Fair enough!

Jackie: Yeah reach out to me on LinkedIn, send me a message. Happy to chat. I think product's super interesting and as we're moving in the generation and the space that we're moving in now, I think product is gonna be more and more important in the future.

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