Finding Your Own Path to Innovation with Natasha Jakubowski

Her Story to the Top

 Guest: Natasha Jakubowski, Chief Innovation Officer & Global Partner, Anomaly

Episode Overview

In this episode of Her Story to the Top, Helen Vaysman speaks with Natasha Jakubowski, Chief Innovation Officer and Global Partner at Anomaly. Natasha shares her unconventional career journey, insights into innovation and leadership, and what she's learned from interviewing successful founders on her own podcast, Professional Jealousy.

From moving to the U.S. without a clear plan to helping companies develop breakthrough products and experiences, Natasha’s story highlights the power of curiosity, adaptability, and the courage to try something new.

This conversation explores leadership, career growth, balancing family and ambition, and how AI is reshaping the future of marketing and innovation.

In This Episode, We Discuss:

• How Natasha built a career without a traditional plan
• Transitioning from advertising strategy to innovation leadership
• Why trying — even imperfectly — matters more than overthinking
• The realities of balancing career success and family life
• Leadership lessons learned without formal training
• The future of marketing in an AI-driven world
• Why developing your own voice matters more than ever
• Career advice for young professionals entering marketing and innovation
• Natasha’s passion projects and advisory ambitions
• The story behind Disney’s MagicBand and other innovation work

Key Takeaways

1. You don’t need a perfect career plan
Natasha built her career by identifying what she enjoyed — and gradually removing what she didn’t.

2. Try more, overthink less
A major lesson from interviewing successful founders:
"Do I have more to lose by not trying?" became a guiding question.

3. Leadership is built over time
Natasha emphasizes kindness, transparency, and communication as essential leadership skills — even without formal training.

4. AI is reshaping marketing
Future professionals should:

• Learn AI tools
• Use AI as a thinking partner
• Develop expertise in a niche
• Create content to build their voice

5. Recognition matters
Simple feedback and acknowledgment can have more impact than monetary rewards, especially for junior team members.

About the Podcast

Her Story to the Top brings you real conversations with female leaders who have claimed their seat at the C-Suite table — sharing the lessons, challenges, and breakthroughs along the way.

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Transcript

SPEAKER_01 0:00

If I'm hypercritical, I could have tried more stuff. And maybe I didn't, but I did think about it. So I I think of one other big takeout is that do I have more to lose by not trying? Is probably the question.

SPEAKER_00 0:17

Welcome to her story to the top. I'm Yanna Blackwilder and I'm co-founder of C-Suite Readiness. My name is Helen Baseman, and I'm a co-founder of C-Suite Readiness. In this podcast, we will bring you the stories of those women who've made it to the C-Suite and became successful founders. No flops, no pretends, just real stories and real insights of what it took to make it to the top. Hi, Natasha. Welcome to the first story to the top. We're so excited to have you here with us. Would you mind introducing yourself and telling our audience a little bit about yourself?

SPEAKER_01 0:58

Well, thank you for having me. My name is Natasha Jacobowski, and I am Chief Innovation Officer and a global partner at a company called Anomaly. And I always realize that Chief Innovation Officer at Anomaly sounds very vague, and everyone's like, what exactly does that mean? Well, I'm a strategist by background, and I help companies, usually big companies, although increasingly I try and look for some startups to help as well. But I help companies find new ways to grow. So that could be new business ideas, new brands, new products, new experiences, basically working with them to solve business challenges and figure out how to how to grow and thrive, hopefully.

SPEAKER_00 1:48

So looking at your background a little bit, you got your first class honors from Oxford University and a master's in media communications. So what led you to this role of innovation?

SPEAKER_01 2:02

I'm quite interested in how people get to where they get to. And I think one of the reasons I'm so interested is because I've always felt like I haven't had a plan. And I think that's because I was never sure what my passion was. After my master's, I got a job what helping at the BBC writing documentaries. I moved age 25 to America because a friend of mine got a job here and was like, get a job and we can live together. And so I was like, Yes, I'm gonna get a job. And today no one would give me a visa, I don't think. But I managed to get a visa and I moved three weeks later. But yeah, so that's that's kind of my career journey. I ended up in innovation from strategy in advertising because I realized that my end, my a lot of an advertising strategist is about briefing a creative team who then comes up with the the creative ad. And I realized probably 15 years ago that it was very frustrating as a strategist to have the end of your role be briefing a creative team. And so I found multiple ways to take the strategic leap by myself and help clients with new ideas that weren't words and pictures, which I can't, I don't want to write ads, I'm not good at that. But I found other ways to basically help brands and businesses grow that didn't involve advertising but could involve a new strategy for reaching a new target or using design to reinvent how they kind of come across or a new product to acquire new types of consumers. And so I basically realized that I had other ways to use my strategic skills to help companies, and and that's how I moved from advertising strategy through to a broader kind of brand strategy and innovation strategy.

SPEAKER_00 4:00

So it sounds like having no plan turns into quite a plan and creating a sort of like niche within your industry and creating Yeah, I kind of versus one big plan, I kind of figured out what I did and didn't like to do.

SPEAKER_01 4:15

So I got rid of as many things that I didn't like to do and I focused on things that I did like to do. Now, I still always think, should I be doing something else? But the truth is I'm happy with my job because I've created a role where I do do things that I'm I'm really enjoying, and I try and minimize the things that I don't enjoy. And that's that's kind of been my career process.

SPEAKER_00 4:41

You have launched something new, which I would assume is a bit of a passion project. It's a podcast as well. It's called Professional Jealousy, and you've interviewed some incredible guests so far. Anybody like Rebecca Minkoff or the founder of Fleur DeMall, which is a lingerie brand, to AI Google fund.

SPEAKER_01 5:03

Well, thank you for the plug. Everyone listening should subscribe, follow. Yeah, exactly. You can find it wherever you listen to or look at, watch podcasts. And I realized that podcasting would be a great way for someone who is actually slightly introverted. Doing something new, doing something I enjoy, meeting interesting people. A lot of the people that I've interviewed, I haven't someone's introduced me to, and I so I didn't know. And it's been fun learning something new. I created my first website, which I assumed was going to be pretty easy with all these ads from different vibe coding and all this stuff. It was hard. But I've now on I'm releasing episode 14 next week with the founder of Dagny Jover. Got like 10 more already recorded. Yeah, it's interesting.

SPEAKER_00 5:53

So, from what have you learned about your own career from interviewing these, from interviewing your podcast guests?

SPEAKER_01 6:00

Realizing that you can be successful in lots of different ways is one big insight. I think there is a couple of others that sound blindingly simple, but like you don't get anywhere without like asking for it, without doing something about it. So one of the big insights is also that all these people have kind of put themselves out there and just tried instead of thinking about it. If I'm hyper-critical, I could have tried more stuff, and maybe I didn't, but I did think about it. So I I think one other big takeout is that do I have more to lose by not trying? Is probably the question. I've just come back from Japan where I was a keynote opening up a conference in Tokyo for like 600 people, so that was fun. I don't think that was a chance, that was just an amazing opportunity that I was offered. So I think versus big challenges, I'm open to more and more challenges. I think I'm at a point where my kids are a bit older, I feel like I still have the drive to do new things. I'm trying the podcast, I'm actively looking to help startups and founders and be an advisor or a board member. Like I'm looking now for more opportunities like that because I think that it's the sort of thing that will help me grow beyond my everyday job as a kind of full-time worker in the innovation space. So I think I can expand by doing more advisory and and and again probably helping some smaller companies than than I am doing in my day job.

SPEAKER_00 7:40

What would you say is the biggest challenge, like living in New York City, navigating family and a successful career? What's been the biggest challenge for you?

SPEAKER_01 7:49

I think the the biggest challenge is probably self-inflicted. It's that feeling of guilt. Am I spending enough time with my kids? I think now I'm getting increasingly worried as my tenth grader starts thinking about college. Like now I'm getting worried that oh my god, I'm gonna be losing my kids soon. They're getting old and like now I'm getting the fear that I don't have much time left with them.

SPEAKER_00 8:18

As I've been listening to you talk about sort of like your journey to where you are now, it's like what advice would you have would you give someone trying to break into marketing or innovation strategy? Like, I mean, I know you've mentioned things like saying yes, challenging yourself, asking the right questions, but is there maybe one particular lesson that comes to mind?

SPEAKER_01 8:41

I feel like marketing is one of those industries that is already, I mean, I guess a lot of industries are, but you know, it it's an interesting time with AI and clients using more AI, both whether it's on the creative and the content production side or it's on the kind of analyst and kind of data side. Those are two areas where AI actually is turning out to be pretty good. So I think the marketing world is definitely more under pressure than ever. I would say if I was talking to a a young person, I I don't I'm not sure I would start looking for a role on the agency side because I worry that the so as a service industry within this space it's gonna get harder and harder. So moving towards a client-side role, I think, would be a good thing to think about. In terms of strategy, I think again, getting really comfortable with a lot of the AI tools and not using them purely to give you the answer, but understanding how you can use them as a co-pilot or a way to save time and to actually accelerate your thinking versus f just rely on it for the answer. Like I'm seeing more and more pieces of work where I'm like, ah, that's just AI. You actually need to take that, and it's definitely a crazy market out there. I would say think client side before agency, think about how you get really smart and good at all these amazing AI tools that are coming out so that you're on top of them versus trying to catch up. Use them to help create an expertise. I think more and more being really smart at something, whether and that I often tell juniors like, get smart something so someone internally knows that you're the person to go to for Gen Alpha insights or social media hacks or something, like get smart and known for something, and then create content, like push yourself to create stuff so that you're honing your voice, whether that's a Substack or a newsletter or just uh an old-fashioned kind of blog or journal, even if you don't show anyone, like start really thinking about you think about stuff. I think that's gonna be more and more important to kind of define your voice in a world of AI slot.

SPEAKER_00 11:11

So the name of our podcast is her story to the top, and as we know it's not always a smooth road. And if you feel comfortable, can you share maybe some maybe fumbles or like stumbling blocks that sort of led through a break breakthrough and making the next step that had made have made a difference in your career?

SPEAKER_01 11:33

It's not really answering it, but I've stayed at one company for a long time, so you know the benefit of that is that I've had a safe space where I've known my position and I've created a position with trust and over 18 years. So I don't have any big fumbles really in the last because I've kind of it's hard to think of in terms of macro career. I mean I've stayed at the same place. Maybe that's my fumble.

SPEAKER_00 12:07

I don't think it is.

SPEAKER_01 12:09

And I'm sure, like on client business, there are there are things all the time that could go wrong. And I think usually it's about communication. I think some of if I really think about the times where I feel disappointed in how I've performed, it's usually about not leaning in and showing leadership. I think it's very easy to just kind of let things drift versus actually take control of a situation and try and make them better. So I am thinking actually of something recently on a client business where there were loads there were almost too many senior people involved. And because of that, I probably took a a step back thinking everyone else is going to sort this out. But actually, I probably could have done more to make it to fix it than I did. And I actually have thought about that as that was a bit of a fail, a personal fail.

SPEAKER_00 13:08

Not that anyone else necessarily thought that so you must be reading my mind because my next question I want to ask is that obviously because you've been in this position for so many years, and you do have a senior role, and you lead a lot of junior associates who look up to you. So I was going to ask you about sort of what leadership skills do you find have helped you along the way.

SPEAKER_01 13:32

I mean, I think I definitely have a slight insecurity. I mean, one of the benefits of growing in the same company is that I've kind of built my own world. I now feel like I control, I'm at a senior position in the company. I think one of the downsides actually is that I don't think I necessarily had a ton of leadership training or mentors. I started at anomaly as a partner. So I kind of started 18 years ago, rightly or wrongly, very senior. And so I I think one of the things that I sometimes think about is I probably could have gotten better at traditional leadership training and skills. So I feel like I kind of cobbled them together and probably thought about that more in the last 10 years than I did in my first uh 10 years at anomaly. So I don't know. I think I think there are some basics around kindness and empathy and understanding where people are on the team, the importance of transparency. And I can I can be pretty blunt, like, and I really I'm not a great small talk. I when something's wrong, I I definitely I I probably I'm a little too quick to just talk about what's wrong. And I think that can be sometimes a little, I need to watch that it doesn't come across as too harsh, but but I do think transparency and understanding that it's not personal, but really figuring out what stuff needs to be talked about and what expectations are is important, and then communication like the worst possible thing is I I often think it's interesting that times when someone is doing really well on a team, you kind of leave them alone because you don't need to worry about them, and then sometimes that can feel for the person being great like they're they're just being ignored, and it and it's actually the opposite, you're you're leaving them alone because you don't need to deal with them, you can deal with all the other problems because you know they're going to be great, and so understanding, always remembering that even if someone is your your second in command or someone that you can rely on, you just need to remember that they still need to hear good feedback and have communication. So I think those are a few of the things that I've learned along the way.

SPEAKER_00 16:05

Well, this is a good time to plug C-suite readiness, because that's a place where someone can hone in on their leadership skills or get executive coaching. Because it's showing Yeah, what are the things that you would suggest?

SPEAKER_01 16:18

What are what are some things that you think help senior women that haven't had any formal properties that learners?

SPEAKER_00 16:26

I think coaching is a great tool. I think there are a lot of leadership programs that provide skills. A lot of these things are a lot of these things almost work like a formula, right? If you do A, B happens, for example, what you said that about somebody who's doing well on the team, right? What are some of the easiest ways to encourage your employees or your juniors? Of course, there's pay, right? Because we all live in your city and life is expensive, but that's not always enough. People want to be recognized, people want to be acknowledged. There has to be some sort of like a reward system, and I think also it's important to not just have leadership training for just the senior partners, which often happens in which often happens, right? Where like the senior partners get the training, but it's all the junior partners, right? It's a junior person who perhaps in two years is gonna be leading a team. And although somebody could be a very cre in your business, could be a very creative person, and they're very good at client interface, and all of a sudden they're placed in a position where they're now managing a team, but they don't have those skills and the tools. Yeah. So I think as a senior leader, although it's important to to obtain the training for yourself, whether it's through leadership programs or just executive coaching, but I think it's equally important to recognize that it's not just the senior members who need the training, it sort of needs to trickle down, and that way as your staff sort of like moves up the ladder, they're prepared and you have those like mechanisms in place. Great point sort of I I I think it's more than just the senior the senior members getting the training. Because it's very difficult, also, I think, in especially in your business, if someone is super creative and they can come up with a great campaign and a great idea, and then all of a sudden it's a month or two months later, and you're in a meeting with your clients and you have to present it. And I feel like a lot of people sometimes fumble that, right? Because it's much easier to sort of sit at your desk and do your work and come up with the ideas, yeah. Drawings of you know, what whatever that may be, or you're very good with AI, but all of a sudden you have to translate those ideas to a client who is a you know, sort of like a lay person, right? That's often not something creative, it's just a business person where, like, okay, like how does it do the numbers add up? So I think a lot of times it's important to recognize that this training should be sort of done like from bottom up, and everybody should have a different level of training, and I think it really changes the culture of the yeah, of the state. And and I and I will tell you, a lot of it is if you decide to partake in any of these leadership programs, hopefully with us, or to get, or if you would like to bring our sort of like associates to do some training for your employees, you really will see that a lot of it is a formula. It's it could be easy sending that employee, you know what, like you did great, like this was a great week, you performed so well in the meeting, and people really appreciate it sometimes more than the than the monetary sort of rewards, right? Whereas I think someone who's in the senior role, your responsibilities are also very different, and you're also have a lot of fiscal things that you need to be cognizant of that may take priority over somebody sending you. Oh, Natasha, great job. You did so well at this conference. Because you probably you got here, so you're no, you did great at that conference. You may not need that email, but whereas someone younger and in a different position may appreciate that email and it could it could change their day, it could change their outlook on things.

SPEAKER_01 20:39

Yeah, yeah, yeah. No, it's it's so true, so true. Definitely, I'm like literally, who am I gonna write to straight off?

SPEAKER_00 20:46

A little plug for all of us. So, where do you see yourself in the next five years in your career? Well, let's it's a two-prong with your career, and also I've listened to your podcast. You have amazing guests. I mean, I obviously, whether it's for the business or wherever people you're introduced to, you're definitely getting some very interesting and successful and brave guests. So let's start. Where where do you see your career in five years? And where would where would you like to go with your podcast?

SPEAKER_01 21:18

I think career-wise, I think it's about finding more and more opportunities to do advisory and maybe board work to kind of broaden my experience. I found it so interesting because I have such a consultancy business. I work on one day I'll be working on beauty, the next day I'll be working on hardcore CPG, the next day I'll be working in like fintech or digital kind of shopping or theme parks. I mean, like I I work on so many different categories so often that I think it's been really interesting as an advisor outside. Of these big companies because it it's quite valuable to have so many different perspectives from so many different categories and types of business challenges. So I think that's one thing for my career that I'm I'm interested in doing more of. And now that my kids are older, as I mentioned, I just came back from this Tokyo conference. I'm quite happy to fly off to other conferences if they're willing to pay for me to come and speak. So that's definitely I I don't think that's a goal, but if that happened again, I would do that. I think in terms of the podcast, it's interesting. I've had a couple of offers to to have some to read an ad for something. And at the moment, I'm I'm happy not trying to sell a product or advertising anything. Now, I will say that's because the the sponsorship fee that I would have been paid is just like I don't think it's worth it that to to suddenly start having advertising on it because I'm still pretty small potatoes. So I don't know. I'm gonna carry on. The podcast is I do it myself, and it's it's not no work, but it's a little bit of work, but it's still manageable so that I can do it uh above and beyond everything else going on in my life. So I'm quite happy to keep doing that. My plan is to continue recording and releasing every two weeks. I would love to see how that grows. I've had a lot of founders on my podcast just because of my network, and I plan to start bringing in more CEOs or C-suite beyond founders. So that's one short-term goal. But yeah, I'm I'm looking to see. I'm at thir over 30,000 at the moment. Yeah, I'm wondering how big this can, how many, how many views can I get? I don't know. Well, it sounds very exciting.

SPEAKER_00 23:58

Like you can really grow this podcast into something much bigger than what you had maybe even intended to be.

SPEAKER_01 24:05

Yeah, maybe. I mean, yeah, we'll see. I mean, it's still it's still a uh kind of business-y focus. Like, I don't think it's gonna, it's not like a mainstream thing, but for now, it's definitely worth it.

SPEAKER_00 24:17

What's a couple of the most fun projects you have worked on? I know of a couple that I can think of that you worked on, but I'm curious to see what you will say.

SPEAKER_01 24:27

I mean, I've been at Anomaly a long time. So there's so many. I've worked on I've literally worked on so many projects over almost 20 years. I think some of the ones that I'm particularly proud of, this is a long time. I mean, it's probably like I actually can I know when I finished it because I was heavily pregnant with my son. So almost 16 years ago, I worked, I did a long project for Disney World Parks, where we basically went into the theme parks and started thinking about how to how to evolve the fixed infrastructure. If you think of Disney, it was finished in the 1970s, and then they basically replicated the Florida park around the world. And when we did the project, suddenly they're crowded, they're not interactive. When every kid thinks you can kind of touch a screen and instead you're walking around something waiting in lines. So the project was all about basically figuring out how to use technology and solve some of the pain points in the parks. And we came up with the Disney Magic band and we did the initial prototypes, and now when I see that I'm like, that's kind of amazing. Like that is yeah, so I'm pretty proud of that, and then oh my god, I mean, I'm proud of so many, so many things. I mean, I've worked in space travel with Blue Origin. I've worked on I loved working with Procto and Gamble for many years. I worked with their ventures on new brands and new products. At the moment, I'm working with an amazing female founder who has created a new way to solve, to prevent female incontinence, and she's just getting ready to raise money. She needs to raise money. So that's an exciting one because I would love her to. We've done the branding and and helped her with kind of visual identity and strategy. I would love to see that get funded and launch and help millions of women with this awful, this terrible kind of female health problem. So yeah, so many. What are the ones you were gonna say?

SPEAKER_00 26:36

Well, actually Disney. I remembered the plants.

SPEAKER_01 26:41

Yeah, it's a thrill seeing things that you actually like. I helped do that.

SPEAKER_00 26:45

Well, or the or when I mentioned that we had an event at Nordstrom's and you had responded.

SPEAKER_01 26:52

Oh yeah, yeah. Love that. Yeah, I I I created the Naughty Club, reinventing the Nordstrom Awards into a uh more of a kind of a better membership idea, and and created the name and the branding and the visual identity for the Nordi Club. Yeah. So many things. And so many that got killed and never launched or or failed in market.

SPEAKER_00 27:14

And maybe we can do the play mahjong soon and actually know what we're doing. I hope so. Yeah, that sounds good. Thank you so much for speaking to me. This has been so much. And I hope to see you at some of our next events. And I can't wait to see you know what incredible guests you have on Professional Jealousy.

SPEAKER_01 27:36

I know, I'm looking forward to seeing your podcast come to life.

SPEAKER_00 27:40

Yeah, so we're also we have two episodes that have launched, and we have a few more sort of in the bank, and we'll start releasing them shortly. But this is a journey. This is definitely also for myself. But yeah, you know, I'm a pretty private person, so I know putting yourself out there. Putting myself out there, but as you said, what we learned from these founders who have succeeded, right? It's not about it's about asking the question and actually doing it, right? Yes, of course, nobody sees the little failures or the no's along the way, but it doesn't matter. It takes one yes, it's sort of like a numbers game, and you just have to do it. Thank you so much for taking the time today. It's been really exciting. I can't wait to have this episode go live and for people to learn about your journey and to learn about your podcast. And hopefully, you can have us at Anomaly, and maybe we can do a little workshop. No shame in my game, obviously. And um, yeah, let's I am excited about Mahjong. I think I am gonna do a lessons again. All right, yeah, and maybe you can join us for our next Canasta event. A lot of women really enjoy.

SPEAKER_01 28:53

I mean, I don't know how to I need to learn how to do that.

SPEAKER_00 28:55

Yeah, people there was somebody to speak.

SPEAKER_01 28:58

Okay, yeah, yeah, yeah. Let's go.

SPEAKER_00 28:59

Yes, so enjoy the rest of your day, and I'll speak to you soon. I'll speak to you soon. Thank you so much. Bye. Bye. Thank you for listening to her story to the top, where we bring you real stories, real conversations with real female leaders who have claimed their seat at the C-Suite table. We hope these stories and our conversations will inspire you to take the next leap and to grow in your professional journey. You can follow us at C SuiteReadiness on Instagram and please check out csuitereadiness.com for more resources. Also, you can check our YouTube channel at C SuiteReadiness.