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From design desk to product lead
How Transitioning from Product Design to Product Lead Fostered Growth, Tackled Challenges, and Offered Insights for Strategic Success
Have you ever felt that you have much more to give but your role or title prevents you from doing so? I have felt this way several times throughout my career, from my first job as a graphic designer to becoming an Art-Director, and then switching to a Senior Product-Designer and a Design-Lead.
Whether you’re a solo designer, a member of a design team, a junior or senior designer, a design lead, or the head of design, you probably know the significant impact you have on the final product and the process.
It is an overused cliché to mention how today’s designers are not only creating sleek products but also solving complex product issues and transforming great ideas into amazing products and exceptional experiences, all while emphasizing real value. Despite this, many designers often remain blind to the business side of the products they work on.
I’m not here to say whether this approach is right or wrong because it depends on the business, the product, the culture, and the designers themselves. However, I know that many designers seek to provide better value and expect a deeper understanding of the business side to unlock their full potential.
The tech industry today is evolving faster than ever, with new technologies rapidly entering our lives. None of us should feel comfortable in our roles. We must keep up to provide real value with a better perspective.
My career began as a digital designer 15 years ago, quickly evolving into an Art-Director. My path then led me to the tech industry, where I embraced the role of a Product Designer. Along this journey, I cultivated a unique perspective on Product Management, eventually mastering it. Design remains my primary skill, a constant in both design and product management roles. It’s also my greatest advantage.
What to expect from this article?
In this blog post, I’ll share the insights and experiences of navigating the dual roles of Product Manager and Product Designer, showcasing the fusion of creativity and strategy that has defined my career. Join me as I explore the practical lessons and real-world challenges that come with balancing these two roles in the tech industry.
What you won’t find here ❌
- A 5-step guide on how to become a better professional.
- Quick tips to find your next job.
- More methods to enhance your design system on Figma.
- Content marketing aimed at selling you another tool you don’t really need.
What you will find here ✅
- An honest, first-person account of my journey from designer to product leader.
- Insights on how I leveraged my design skills to excel in product management.
- The obstacles I faced and the lessons I learned along the way.
- How my design background gave me a unique edge in product strategy.
- Practical advice and real-world experiences that shaped my approach.
Chapter I— Leveraging Design as My Core Skill
As a child, I was fascinated with building things I couldn’t have. I would collect boxes and craft small racing cars, planes that never really managed to fly, and everything I dreamed of having but couldn’t afford. The thought of building something that would actually work, then publishing it and bringing my dreams to life, could keep me glued to my chair all summer. Years later, I am still that boy, planning, building, and crafting a world from scratch.
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I have learned how to build the best user experience based on deep research and skills, creating a tailor-made design system that will be adaptable for years to come. I can take any vision into reality with a development-friendly UI that saves companies time and money while keeping users happy.
Designers today are much more involved in critical product processes and decisions. The designer often serves as the glue between R&D and Product.
Some companies even allow their designers to lead parts of the product and make real data-driven decisions, further blurring the lines between Product Management and Product Design.
I WANT MORE.
With all the above being said, after years of striving to be the best Product Designer I could, I started feeling a sense of lack.
Holistic View
Product managers are responsible for the overall strategy and success of a product. They have a holistic view, considering market research, user needs, business goals, and technical constraints. This broad perspective can be intellectually stimulating.
Decision-Making
Product managers often have the final say in product decisions. They have the authority to set priorities, make trade-offs, and decide the product’s direction. This can be empowering and provide a sense of ownership.
Market and Business Focus
Product managers are closely aligned with the business side of the organization. They work on market research, revenue generation, and business strategy, which can be rewarding for those interested in the commercial aspects of a product.
Designing the Route
During my time as a product design contractor, I worked with many startups and accelerators in the local tech industry. The opportunity to collaborate with a diverse range of companies at various stages was the most significant and rewarding leap in my career.
Building product presentations and pitches for early-stage startups, developing the products they promised to investors, and maintaining those products as we gathered users and data was undoubtedly the best learning experience I’ve ever had (I will tell you more about it later on).
During that time, I met Dan Peleg, the Founder & CEO of GlobeKeeper, in its very early days. He became a dear friend and someone I worked with around the clock, more intensely than I could have imagined
‘Connnect’ by GlobeKeeper is an end-to-end encrypted communication platform for the security industry worldwide, used by the largest law enforcement organizations, especially in Europe.
While juggling multiple projects, GlobeKeeper captured most of my attention. In my free time, I would meet with Dan to discuss the product and how we could improve it.
Three years later, after building a great relationship with Dan and GlobeKeeper, we decided to take it to the next level by having me join as a Product & Design leader in a company that had previously relied on external product and design contractors.
This was just the beginning of what would become the biggest and most challenging experience of my career.
We redefined the target market and users, built a new product roadmap, conducted an extensive number of interviews with industry professionals, developed a new R&D cycle, rebuilt a team across the globe, crafted a new design system, and planned a product our market truly needed.
There are many things to say, numerous methods, and many mistakes made during the process, but I will elaborate on those in a separate post in the future.
It’s not what I thought
In the beginning, I really believed I could do it all. I saw the picture clearly and didn’t mind staying awake all night, every night, to deliver my best. The company was on the brink of exhausting its funds, right before a new round of funding, but COVID had just struck, drastically altering our plans.
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With a limited budget and the initial idea that I could handle everything — from strategy, planning, and design to delivery to R&D and everything that follows — I realized how foolish I had been and faced the harsh reality.
The fact that we were entering a completely new market with new rules and users made the experience even harder and more frustrating. Because we were working in a sensitive industry, my access to real data was severely limited.
It became clear that I couldn’t do everything, but I also didn’t have anyone else to take on the workload. I started to do the thing designers hate the most and go against my basic instincts:
Welcome to the World of Compromises
As a designer, I always aimed for the most polished product, a sleek UI, an exciting UX, and unique tweaks that would make my design stand out above the rest.
Early in my career, I was frustrated by the need to find an “easy way” to do things at the expense of other aspects. I always heard about budget and time limitations, but it never made me feel better and often left me frustrated, feeling I wasn’t pursuing my professional goals.
Once I entered the tech world, I understood the necessity of the POC (Proof of Concept) process and always supported it as a bridge to creating the right product. I insisted that many of my clients have a thorough and insightful POC before moving on and wasting their budget on costly mistakes.
However, having a good POC and moving on to a successful POV (Proof of Value), collecting data, and winning the game as described in the textbooks is not the reality for many small companies.
The truth is that often you won’t have enough data, especially with classified clients and on-premise users. Many times, the POC will consume time you don’t have, and sometimes you must release a feature because the company’s survival is at stake.
Chapter II— Finding My Champion
One of our first major projects was the user onboarding workflow for on-premise users. This process is complex because the servers are not associated with the end user when they first access the system.
We are not the only company to experience this challenge, but every company has different clients, needs, and levels of security. In our case, we faced the worst of everything. Our client is one of the largest and most prominent institutions in the world, and any security compromise, even if it doesn’t seem significant, would cause major friction.
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Our only way to ensure we weren’t wasting our remaining resources on another huge mistake was to involve our client in the process.
We needed to be transparent with them, allowing them to feel that we were working on the right solution while also ensuring their commitment to the outcome.
Of course, this approach won’t work with every company or every client. It’s not a perfect solution and can be challenging when you have many clients who might see the feature differently. However, our luck (and also curse) was that our product was in its early stages, with few clients, and that specific client was a real industry standard leader.
We could definitely rely on them.
To make things work and deepen our relationship with the client, I needed to find someone who could be my ‘go-to’ person within their organization — someone who could help push things forward and feel a real connection to our product.
Shortly after working with our great client team, the main project manager was replaced by a new one. Although the previous project manager was excellent and had become an expert on the project over time, new blood was exactly what I needed.
The new project manager was fully engaged and had a lot to prove to his own organization. I knew we could leverage this to benefit our product and project. This relationship had to be mutual, with both sides benefiting.
To build such a beneficial relationship, we must consider three different factors and follow them repeatedly. These three factors are interconnected and cannot work as standalone elements.
Trust
Clear and Transparent Communication
- Regular Updates: Provide consistent updates on project progress, timelines, and any changes through emails, reports, or scheduled meetings. Keeping the client informed builds confidence in the project’s direction.
- Honesty: Be honest about potential challenges, delays, or issues. Clients appreciate transparency and realistic expectations, which foster trust and prevent misunderstandings.
Reliability and Accountability
- Consistent Quality: Maintain a high level of quality in every interaction and deliverable. Ensuring that the product and services consistently meet or exceed expectations builds a reputation for reliability.
- Ownership: Take responsibility for mistakes and make efforts to correct them swiftly. Demonstrating accountability shows clients that you are committed to their success and builds trust.
Build Strong Relationships
- Personal Interaction: Foster a personal connection by getting to know key stakeholders. Show genuine interest in their success and well-being to create a strong rapport.
- Regular Check-ins: Schedule regular check-ins to discuss progress, gather feedback, and make necessary adjustments. These interactions help to keep the client engaged and reassured.
Skills
Proactive Problem Solving
- Anticipate Needs: Anticipate potential issues and address them before they become problems. Being proactive in identifying and mitigating risks showcases your foresight and dedication.
- Provide Solutions: When issues arise, offer actionable solutions promptly rather than just highlighting the problems. Clients value partners who can solve challenges efficiently.
Deliver Value Consistently
- High-Quality Product: Ensure your product meets or exceeds expectations in terms of functionality, usability, and reliability. A high-quality product is fundamental to client satisfaction.
- Timely Delivery: Meet deadlines and deliverables consistently to build a reputation for reliability. Timely delivery demonstrates your ability to manage projects effectively.
Knowledge
Understand Client Needs
- Active Listening: Engage in active listening during meetings to understand the client’s business goals, challenges, and specific needs. This shows that you value their input and are focused on their success.
- Personalization: Tailor your approach and solutions to address their unique requirements. Demonstrating that you can adapt to their specific needs highlights your flexibility and commitment.
Showcase Success
- Share Case Studies: Present case studies or success stories that highlight your past successes and how your product has helped other clients. Sharing these examples builds credibility and trust.
- Demonstrate ROI: Provide metrics and reports that clearly show the return on investment (ROI) your product delivers. Quantifying the value of your product helps clients see the tangible benefits.
Continuous Improvement
- Feedback Loop: Implement a feedback loop where clients can provide input on the product and their experience. Use this feedback to make continuous improvements, showing that you are committed to evolving and meeting their needs.
- Innovation: Stay ahead of industry trends and continuously improve your product to provide cutting-edge solutions. Innovation demonstrates your dedication to staying relevant and offering the best possible service.
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In the meantime, I released a user survey to our client, asking them to share their desired features, needs, solutions, and their experience so far with our old product. This approach allowed us to focus on the areas that needed attention and avoid further mistakes in a product that is rarely data-driven due to the circumstances.
The process with the client became one of our main tools for achieving a strong relationship between them and our company. We continued these sessions for many other critical features, continuously adjusting and fine-tuning the process.
Chapter III — Find New Opportunities Wherever You Are
While working with many great PMs during my career as a designer, I learned their methods, perspectives, and a bit about product strategy. However, it was actually my time as a freelance design contractor that led me to realize I wanted to be more involved in the product process beyond my role as a Product Designer.
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Working with many early-stage startups, which often lacked a proper PM to lead their product, gave me the opportunity to push the boundaries of the designer role a bit further. One of my biggest lessons came from working on investment presentations as part of the companies’ fundraising efforts.
Being exposed to the product’s vision and strategy highlighted my lack of knowledge at the time and underscored how much I needed to learn to create products aligned with real numbers. Terms like “Value Proposition” and “Product Market Fit” initially seemed like buzzwords, but over time, they became fundamental concepts in my approach and thinking.
Why My Design Skills Made the Difference
Years into my work at GlobeKeeper, I strived to maintain a balance between the designer and the product leader within me. It wasn’t always easy, but the benefits were substantial.
- Building a Collaborative Team: I built a team of PMs and designers that could work in harmony (most of the time), effectively communicate, and share their knowledge. We learned to guide designers and set expectations while staying aligned with product and business goals.
- Effective Communication: I became better at explaining and delivering my ideas, whether to product managers, designers, developers, or even clients. I could illustrate and build a coherent story based on real ideas and designs.
- Staying Updated: Throughout this time, I made it a priority to stay up-to-date with new design trends, methods, and capabilities.
These experiences in building collaborative teams, effective communication, and staying updated with trends gave me a valuable edge. They allowed me to bridge gaps between design and strategy, driving product success. Embracing these opportunities enhanced my ability to create impactful products, highlighting the importance of a multifaceted approach in any organization.
Chapter IV— From Doing to Managing
Switching from doing everything solo to building a team was a game-changer for me. Initially, I wore so many hats that I barely had time to think about the big picture. Hiring freelancers helped a bit, but I knew we needed a solid, long-term team.
Bringing new team members on board was both nerve-racking and exciting. Each person brought their own unique perspective, and figuring out how to delegate and keep everyone aligned was a learning curve. I quickly realized that being a good leader meant maintaining open communication and ensuring everyone felt valued.
I came into this role with proven management skills from my years as a senior designer, design lead, and art director. Although the new role required a broader skill set and often a completely different approach, the tools I brought with me made a difference and were a real advantage for me as a team leader and product person.
During my time as a designer and design lead, I participated in meetups and conferences focused on the critical day-to-day communication between developers and designers. Many of my friends are developers, which led to numerous discussions about improving our collaboration.
These discussions inspired us to start a new meetup series called “Beyond the Code,” where designers and developers could gather to discuss their challenges, methods, and the future. This experience was one of the best things I did early in my career. Besides getting to know many talented people, it helped build bridges between designers and developers, creating a collaborative space where both sides could contribute to building better environments and products.
I still use some of the methods we discussed back then, but more importantly, I insist on involving designers, product managers, and developers in every part of the project. I seek real ownership within the team.
Despite the ups and downs, growing the team sparked serious creativity and resilience. With a mix of talents, we tackled challenges with fresh ideas and determination. Stepping back from the daily grind allowed me to focus on the big picture — like building relationships with clients and keeping our products on point.
Looking back, transitioning from solo work to leading a team was a wild ride. But it showed me just how powerful teamwork can be when everyone’s on the same page and pushing for the same goals.
Designers as Key Players
Involving designers at the beginning of a process is something we’ve talked about a lot over the years, and at some point, it started to sound like an empty mantra. In many organizations, designers are still not part of the decision-making process, even in areas that fall within their domain. This must change, and it can only change if designers are involved early in the project.
I encourage you to keep your designers fully engaged by including them in more client meetings, product strategy sessions, and planning meetings. Let them see the whole picture. Not only will this make their job more efficient and beneficial, but it will also help them understand business decisions and reduce frustration when they don’t understand why things work in certain ways.
Chapter V — From Tragedy to Strategy
The Hardest Decision Ever — The Story of the ‘SAFE’ App: How We Shut Down a Growing Product to Focus on Our Main Market
What if I told you we shut down a successful product with over 30K users that had grown 300% in six months?
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There were many product and business decisions made before my time at the company, involving various approaches to leverage the product, enter new markets and verticals, and find better opportunities.
One of the biggest opportunities was building a second safety product called ‘SAFE,’ which was directed at the private sector and aimed to help high-risk communities secure themselves.
The ‘SAFE’ app started as a pilot in South Africa, a perfect playground for this specific use case. The high crime rate, including robbery, murder, rape, and kidnapping, was a significant issue due to tensions between communities, with local authorities providing insufficient attention. This situation forced local neighborhoods to protect themselves with fences, cameras, security guards, and any other solutions they could find.
Despite these solutions, the best approach was the dedication of the local communities themselves. From local WhatsApp groups to citizens patrolling day and night to keep their loved ones safe, community involvement was key.
Without going too deep into our solution, we aimed to enhance and improve the current approach by providing a better overview of the community with ultra-secured communication, live location tracking, a dedicated panic button for each local, and, above all, clear communication with the local security company.
The ‘SAFE’ app was a huge success — so much so that we couldn’t provide proper support to the end users, and many local security companies requested their own dashboard to offer their clients the best security solution.
It was both amazing and overwhelming. On one hand, we had everything we wanted: a POC that exceeded expectations and addressed a real need. On the other hand, it was never our main product or market, and it hurt our performance in ‘Connnect,’ which was our bread and butter.
Our initial approach was to try and maintain both solutions and find common ground to scale them. To do that, we needed to understand the potential of our new ‘Community/Personal Security’ market and determine if we could monetize it and build a proper business strategy behind the impressive numbers.
The South African market, which appeared to be one of the largest for this specific solution, wasn’t the best for monetization. The budgets were much lower than in the European or American markets we were familiar with. Even with the possibility of hiring a local team at a lower cost, we couldn’t see any financial potential as an American/European company.
While keeping the South African market as a valuable testing ground, we started to look at Europe and LATAM as potential markets with some common grounds we could replicate. However, after three months of extensive research, we concluded that this venture might come to an end. Despite the impressive potential growth, we couldn’t see how it could turn into a viable business without defocusing us from our main product, ‘Connnect,’ and draining our resources.
Looking at the numbers and timeline, we became convinced that we had to kill our relatively successful product and return to our main duty after bleeding money and putting the company at high risk.
It was a harsh decision, especially because it was a success from our users’ and product performance perspectives. Moreover, ‘SAFE’ literally saved people’s lives. Our users needed us, and we felt we had failed them.
This decision was one of the hardest I had to make (together with the CEO) during my career. Even now, I still hope we can bring ‘SAFE’ back in some form, if not for our business, then for the users who needed it.
Here are some of our main KPIs, highlighting the impact of our strategic decision to focus on our core product:
Resource Allocation Efficiency
Go-to-Market Time Reduction: We reduced the go-to-market time for our main product, ‘Connnect,’ by 12 months.
Feature Planning and Development Cycle: Improved feature planning cut our development cycle by 25% and reduced critical bugs by 33%.
Opportunity Cost:
Resource Gains: We gained an additional 35% in resources.
Burn Rate Reduction: Successfully reduced our burn rate by 140%.
Strategic Alignment
Pipeline Growth: By focusing on one product and a specific market, we increased our sales pipeline by 27%.
These KPIs underscore the significant benefits of our strategic decision, allowing us to allocate resources more effectively, optimize development processes, and enhance our market focus.
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One of the biggest lessons from that experience was how relative success can be, and how numbers can mean the complete opposite when it comes to business and product strategy. Such tough decisions cannot be avoided, even when they seem counterintuitive at first glance.
The original purpose of the ‘SAFE’ app was to test ‘Connnect’ in a new use case, facilitating communication not only between security teams but also between the people they protect.
In hindsight, I would prioritize thorough research before building a product and going to market, even as a POC. It sounds obvious, but it’s easy to be swept away by gut feelings and great ideas on paper before they get out of control.
After the ‘SAFE’ app experience, prioritization became our new obsession. Improving methods and reviewing them became our guiding principle for every decision, no matter how big or small, from prioritizing bugs to features and new business directions.
Chapter VI— Product Strategy vs. Design Strategy
Reading (or listening) to my story might sound like a mess — switching between the worlds of design and product management while trying to maintain a team, satisfy clients, and fulfill the expectations of those who put their trust in you can be overwhelming. Indeed, it might have been a mess from time to time. Design strategy and product strategy are both crucial for building the best product and providing real value to users. However, these two strategies don’t always align and can involve completely different processes with different KPIs.
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Let me draw a line between these two hats I insisted on wearing simultaneously, even though it sometimes looked awkward.
Breaking it down into a few key points might make sense to people from both worlds and beyond.
The comparison between design strategy and product strategy highlights their distinct focuses, key elements, and goals:
Design Strategy
As a designer, my primary focus was always on building the best user experience and interface, based on my personal skills and target users, while keeping things friendly and appealing to the market. To achieve this, I conducted user research to understand our users’ needs and build the right solutions. Wireframing and prototyping were often key elements to communicate our ideas and solutions to stakeholders and the R&D team. Pre-release testing and post-release usability metrics were also essential parts of the process.
All these efforts aimed to enhance the product’s overall user experience — whether by encouraging users to try a new feature, making their interaction with the product more delightful, or exposing them to the real value and purpose of the product.
Main Highlights
Focus: Enhancing user interface and overall experience
Key Elements: User research, wireframing, prototyping, usability testing
Goals: Improve user interaction and enhance user interface
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Product Strategy
In contrast, product strategy focuses on market needs and business goals. It involves key elements such as market research, product roadmap development, feature prioritization, and competitive analysis. The primary goals of a product strategy are to increase market share and achieve business objectives.
Main Highlights
Focus: Market needs and business goals.
Key Elements: Market research, product roadmap development, feature prioritization, competitive analysis.
Goals: Increase market share and achieve business objectives.
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Both strategies are essential for the overall success of a product, each contributing uniquely to its development and market positioning. Understanding and balancing these two approaches can lead to a more cohesive and successful product.
Retrospective & What the Hell Am I
Despite all the experience I brought and the knowledge I thought I had, nothing could truly prepare me for this role. No matter how good I believed I was as a team member or a manager, or how much I thought I knew about the tech world and the startup industry, the reality was a complete shock therapy and a long journey of baby steps into a completely new world with its own rules.
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Reflecting on 4.5 years of dedicating my entire professional (and personal) life to this mission, I can clearly see the cracks along the way. Of course, there are many things I would do differently now, but none of them were in vain.
Key Points
Integrate Design with Strategy: Use your design skills to shape strategic decisions from the start by being involved early in the process, engaging with clients, understanding the market, and working closely with the product team. This approach ensures that your designs address real problems, enhance user experience, and align with business goals for a massive impact.
Embrace Strategic Decision-Making: Regularly reassess and prioritize your projects, making sure you allocate resources wisely and make informed choices that drive long-term success and efficiency.
Enhance Client Collaboration: Build strong relationships with your clients by keeping communication open, seeking their feedback regularly, and involving them in the development process. Identify champions and design partners within the organization who can advocate for your product, build trust, and push the product forward from the inside.
The goal was never about being a VP, Head of, or any other title. As mentioned at the beginning of the article, it was about understanding product development in a deeper manner and being able to influence the process to provide real value. Using my design skills to leverage the way I build and refine the product, seeing the bigger perspective, and making better decisions — whether it’s research, strategy, a PRD, or the best user experience and interface — remains my north star as a product person.
But beyond everything, I’m also a better designer.
The story and the experiences and point of views described are personal and should not use a professional advice.
A big thank you to Kacper Bieda for his invaluable support in managing the product and design.
Pixel-art illustrations by PixelBit4Ever
More about me: www.guyisacar.com & guy.isacar@gmail.com