Rumana Hafesjee is a Digital Transformation executive who started her career in Nestlé S.A., where she quickly rose from a Sales Operations Assistant to Brand Manager. Over the years, Rumana has worked as a product leader across diverse industries, including food and beverage, global print production, and insurance services. After a decade at Guardian Life, where she most recently served as VP of Digital Product Management, Rumana transitioned to fractional leadership, working as a Fractional CxO Leader and Digital Strategy Consultant for ambitious companies looking to grow fast.
In our conversation, Rumana talks about the evolving role of the product executive in today’s era of “the great hesitation.” She shares what it means to reinvent yourself as a leader, the benefits of fractional leadership, and how to find roles that align with the work you want to do.
AI vs. human-centered thinking
How do you balance data-driven decision making and human-centered thinking for product design, particularly when it comes to scaling solutions and trying to keep things personalized for users?
Ideally, your data should support the human-centered thinking and design that you want. But that doesn’t always happen. People often say, “Data doesn’t lie.” But sometimes, the data does lie, or it’s not completely honest. You have to be able to discern whether what you’re seeing is viable for your product design or not.
Good data, particularly for product managers, is critical for being able to make decisions quickly and for understanding what’s happening with your users, especially if you work in a specific experience platform. Not understanding your users or your target customers can put you at a real disadvantage.
Can you give an example that demonstrates finding this balance?
You’ve probably heard that people are starting to put their health-related data into generative AI tools (LLMs) like ChatGPT to get medical diagnoses. These models are very sophisticated, so users may get a fairly accurate response in a matter of seconds, and they might think they don’t need to see a doctor.
If you put some symptoms into the model and it tells you that you have the flu, you’re probably going to be satisfied with that result. But what if you put in an MRI result or an X-ray, which some people have started doing, and the AI engine tells you, “This could be cancer”? For those kinds of sensitive results, I believe users would prefer a human touch.
Within the healthcare space, there have been many conversations about how to keep these language models responsible, which doesn’t just mean answering queries as quickly as possible and making a diagnosis, but knowing the best approach for sharing information that might be difficult to hear.
What do you do in the moments where you have data that’s telling you one thing, and you have to use human judgment to take things in a different direction?
When you feel like you don’t have all the information or you’re maybe too close to something, asking internal stakeholders is a great way to get a sense of whether you’re doing the right thing. Use them as a sounding board, and then reframe accordingly.
As a product experience grows in stakes, human intervention becomes more important. For example, I’ve worked in insurance for a decade, dealing with everything from dental insurance to disability insurance. The stakes for these two examples are vastly different: one needs a lot of human interaction and discernment, while the other has a much lower risk-reward ratio.
You have to understand the stakes to know whether automation, or what we call auto-adjudication, is going to be useful to process certain claims. Because, if we get it wrong and deny a claimant the ability to get a dental crown, that’s very different than if we use auto-adjudication for a disability claim where someone has an unfavorable event in their life.
The evolution of product management
How do you think the current environment is changing product management as a role or as a function within a company?
In the age of AI tools and LLMs, analytical product managers will need to learn how to be more nimble and use data to better understand their customers and products more closely than they have had to before. Being able to connect data to the real customer journey fast is going to be key for an effective product manager.
You have used the term “the great hesitation” when describing the current product leadership landscape. How do you see that playing out in companies, and how is it changing the PM leader role? As a leader, how can you sustain momentum and clarity about your own role and expertise in this environment?
There was an article that came out about “the great hesitation,” which is that companies are slowing down and implementing extra checks and balances in their hiring processes. Part of the reason there is hesitation is because there are so many unknowns in the current market, with the impact of emerging AI and technologies. It’s hard to have a clear vision of what the next couple of years are going to look like.
But what I do know is that brands are still willing to pay for complex problem solvers. Recently, Moderna hired 3,000 AI agents, along with a Chief Digital Transformation Officer, to manage the AI agents. So, there’s still expanded opportunity, especially at the senior level, to be able to work their way up.
What advice would you give to product leaders to stay competitive in this environment?
Not all transformation has to be all-encompassing. You can still find low-hanging fruit that will create a large impact. Sometimes it’s basic things like saving costs or automating a manual process. Find a shiny object that you think will sit well with leaders and create education around it, then ask for what you need. Demonstrate your value beyond just your everyday job.
The product manager role is one of the luckiest in this age because it’s right where digital transformation is, but it’s also a role that’s inherently needed. You need somebody to understand the customer to bring a product to market. There’s still a lot of opportunity, even though organizations seem to currently be tightening up their belts.
Traditionally, the trajectory for a product manager was linear – from a junior PM to a senior PM to a director, and so on. Do you think there’s an opportunity to reframe experience, given that you don’t necessarily have to climb the traditional ladder to the top anymore?
100%. That’s been my career. I haven’t had the path of a traditional product manager in the sense that I’ve never been a business analyst, a scrum master, or a tech lead. I came in through marketing. I led digital marketing and customer web experiences, and then went sideways into technology, where I led a product management team.
If I hadn’t done that in my career, I wouldn’t have the ability to morph into multiple roles like I can currently. My background has made me a strong product leader because I came in knowing storytelling and being able to understand customers really well. I could rely on my team members who had come in through more traditional routes, like engineering, to teach me about SAFe Agile, sprint planning, PI (program increment) planning, etc.
Sometimes, people think that if they move laterally, they’ve stopped themselves from moving upwards. But when you move laterally, you have more opportunities in different places to leap up. It just comes down to how you view your career path.
How do you distinguish reinvention as a product leader from simply chasing a title or the hype?
Reinvention means progression and success, and it can also mean financial well-being. These are all very important things. But in the last few years, there has been a democratization of titles based on company, size, industry, etc. These titles can mean so many different things. Being a VP at a small company might directionally relate to being a manager at a large company. It’s important to know what you’re looking for because the title doesn’t always describe your ability to perform that role.
An exercise I recommend people do is to pretend they’re the VP, SVP, or whatever title they think they want, and imagine the work they want to do. Are they happy managing processes? Managing people? Dedicating time to navigating an organization and garnering buy-in? If they’re okay with all of that and doing the work, then great. Otherwise, what is the purpose of wanting that position?
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How did you get to the point of unlearning or reteaching yourself to think about product leadership in this way?
I’ve had to unlearn second-guessing. I never grew up in tech, and I was never an engineer. I came from a marketing and customer experience background. But what I realized is that what I am good at is leading through change. In marketing, everything changes every day. So, as a marketer, you get used to not taking things personally if they don’t go as planned.
The reason I wanted to be in a senior position is that I enjoy managing people and watching their careers flourish. I like being part of their stories and promoting them, especially women and people from diverse backgrounds. I feel like my purpose isn’t only around leading a team or a product, but leading people through their careers.
What is a crucial skill you think product managers should practice in today’s environment?
I think the idea of productizing data is a crucial skill for PMs. Organizations that can find the connective tissue to really understand their customer profiles are going to be set up for success in the next phase of AI-related jobs. Product managers who are not comfortable with data or productizing data are going to fall behind.
For example, let’s take the disability insurance example from before. A PM who is good at productizing data would be able to look at the product and say, “We talked to all these people about disability insurance, but have we talked to them about life insurance? They might be completely different parts of the company, but has anyone tried to cross-sell?”
That kind of thinking is, at times, basic yet critical. I don’t think product managers do it enough. They wait for the business to come to them with ideas about how to evolve a particular product. But PMs can use data from their company in so many ways! Data productization is no longer the job of the data scientist or the team that’s building all the backend processes to merge the data. It’s really the people who are managing the customer at the end of the day.
Fractional product leadership
What kind of mindset shift do you think it takes for a full-time senior leader to make the transition to a fractional or consultative role?
The tech industry is used to outsourcing; we’ve been outsourcing engineers and augmenting portfolios for a very long time. That’s now expanded into product managers, as well. In times of change or uncertainty, companies are still happy to hire senior talent, but just not take them on full-time.
Fractional senior PMs might be hired for a couple of days a week or for project-based work. This is still incredibly rewarding, both financially and from a career standpoint. Fractional leaders don’t just work in one place with one product; they’re now solving multiple problems across multiple places, which is going to make their resume much more appealing in the future because they’ll have diverse experiences.
The mindset that you need in order to take on these roles is one of flexibility, the ability to think non-traditionally, to get uncomfortable, and to know that a full-time job is always going to be waiting for you.
Making big bets as a product leader
In the past few years, what do you think is the boldest bet you’ve made as a product leader?
A big accomplishment of mine was consolidating online experiences. Large companies all come up with several versions of online experiences. Often, what happens during a full-scale company rebrand is that your brand becomes diluted because there are so many experiences, and customers and users don’t know who the real company is anymore.
My role was to consolidate that into one unified experience. The risk was that I was going to kill our SEO for the first three months of the project, which meant that leads were going to drop significantly. But I knew that if we just waited it out, the leads were going to come back.
I was asked questions like, “Why can’t we change all the websites and just not change any of the lead forms?” But I knew that that wasn’t how web experience works; it’s meant to be unified. We had a lot of debate around that. And when we did do the change, the site actually broke on day one! But it was a great learning experience. The first couple of months killed our leads, but then we started seeing much more success. For example, the direct-to-consumer arm of our business, which originally didn’t want to be part of the unified website, ended up getting more leads through organic SEO from the unified site than from its own experience.
It was risky, and it was difficult not to be very popular in our meetings for a few months. But those difficult decisions and a lot of compromising, negotiating, and influencing were all worth it in the end. It takes time for people to understand that you have to lose before you can win.
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