Join us for a captivating conversation with Robert Kaminski of Fletch PMM, where he delves into the essentials of digital product development and startup success. Robert shares his unique insights on the importance of precise positioning and messaging, the strategy of building a market before a product, and reflects on personal and professional turning points. His thoughtful advice and engaging stories promise to inspire and enlighten, making this interview a must-read for SaaS entrepreneurs and enthusiasts alike.

Robert’s Bio

A co-founder and partner at Fletch PMM, where he plays a crucial role in helping early-stage founders find their footing in the competitive tech landscape. With a rich history of consulting with over 100 venture-backed startups, he has honed his skills in developing robust positioning strategies that resonate with target audiences and drive success.

As a founding team member, Robert incubated and launched 3 new products, with 1 still thriving in the market today and co-created an internal incubator for a company created by Vista Equity Group.

Outside of his work at Fletch PMM, he’s taken their passion for product leadership and hosted a podcast that features insightful conversations with industry leaders like Theresa Torres, John Zeratsky, and Ramli John.

Last but not least, Robert captained the GTM innovation program at Oracle, where he showcased their ability to drive innovation and deliver results.


Nat: Diving into the world of early-stage startups, I'm eager to discuss the critical role of positioning in achieving an impeccable product-market fit. Could you start by sharing a bit about your background, what you do, and how you developed your interest in positioning?

Robert: I've spent the last 15 years immersed in the SaaS sector, experiencing a journey across various product domains and teams. My roles have varied, from being a Product Manager to a sales engineer, before I eventually found my true calling in product marketing. This journey allowed me to grasp the nuances of building products from the inside out and approaching the market from a customer-centric perspective.

My partner Anthony and I co-founded Fletch PMM, a consultancy focusing specifically on positioning and messaging for early-stage companies. Our venture into this niche area evolved from our prior roles as product and marketing leaders. We used to offer our expertise as a service, embedding ourselves within companies for extended periods. While this approach had its benefits, it was notably expensive for most startups, prompting us to rethink our model.

We shifted our focus towards early-stage companies, honing in on the aspects of positioning and messaging. Over the past year, this focused approach has enabled us to work with approximately 80 startups, refining our process and learning along the way. We've even gone a step further to open-source our model for developing positioning and messaging, with the hopes to encourage others to adopt our methodology and benefit from it.

Nat: How do you approach the task of identifying the positioning for early-stage startups?

Robert: I think it’s crucial to highlight that the concept of finding the ‘perfect’ positioning when you’re at an early stage is somewhat non-existing. We believe that positioning is perpetually evolving, and there’s never really a moment where you can definitively say, ‘We’ve nailed it!’ This is because positioning is a strategic decision, and even once you’ve decided on a positioning, it doesn’t immediately translate to success. You need to consistently and repeatedly test it in the market.

When early-stage startups come to us, they usually have a positioning hypothesis in place. So, our task isn’t about building a positioning from scratch; it’s more about extracting what they’ve been doing up to that point, understanding their current customer base, and recognizing that they’ve likely tested various approaches and have a diverse group of users. Their main challenge isn’t identifying possible positioning options; it's deciding where to focus their efforts.

Our methodology at Fletch PMM is designed to lay out all the possible positioning options, assess whether the startup has the resources to pursue them all simultaneously, help them decide where to focus, and guide them in making that decision. We view our role as holding up a mirror to these startups, using our frameworks and questions to reflect their current positioning and present them with two to five options for fine-tuning and honing it. That’s our starting point for helping startups navigate the complexities of positioning to achieve product-market fit.

Nat: Do you often encounter situations where startups and founders come back to you with a need to pivot or redefine their positioning?

Robert: It happens quite often. And I must say, these sessions can be intense. There’s a palpable tension as we challenge the founders, highlighting that they can’t pursue every direction at once. It requires a lot of self-awareness and humility on their part, especially since these are typically highly intelligent and hardworking individuals. They sense that something isn’t working as it should, and they’re open to addressing it.

Yes, pivots are a common part of the journey, both down the road and even during our sessions. Founders might come in with a certain idea, but as we delve into the discussions, they start to see other possibilities and may shift their focus on the spot. Our role is to help them navigate through these moments of uncertainty and change.

It’s crucial for founders to remember that they own their positioning, regardless of whether they’re working with us or any other positioning expert. We’re here to guide and present options, but we can’t make the decisions for them. After all, they know their customers and products far better than we ever could. Our job is to provide a framework and a methodology to sift through their ideas and insights, helping to make sense of it all.

However, they need to believe in and commit to the chosen positioning. Positioning is an ongoing task, not a one-off decision. Even if we suggest a positioning strategy that could potentially lead to success, it won’t work unless the founders and their teams are fully invested and energized by it. Their belief in and passion for the strategy is just as crucial as the strategy itself, and that’s why our model is designed to empower founders to feel confident and enthusiastic about their approach to the market.

Nat: Do you have a real-life example to share where your work in defining positioning significantly impacted a startup’s trajectory?

Robert: Absolutely, we have numerous cases to pull from. A common query we get is how startups can ascertain the success of their positioning efforts. Positioning, in many ways, is a subtle and long-term play, not an instant solution to achieving product-market fit. There aren’t always immediate, clear-cut indicators of success following a repositioning.

One interesting case I can share involves a startup named Zox, which was venturing into the AI meeting assistant domain. They developed this intricate contextual AI technology designed to comprehend and capture notes from meetings in specific contexts. Despite the innovation, they faced a challenge common to many startups: their product had a plethora of potential applications, making it unclear who exactly they should target.

When they approached us, we delved deep into understanding who they were building the product for, as well as where the market demonstrated the most significant need for their solution. Eventually, we steered them toward a focused, vertical positioning, centering their efforts on financial advisors.

This shift had a profound impact. Their messaging became sharper, more compelling, and significantly more resonant with their target audience. They started seeing quicker conversions, faster pipeline movement, and an uptick in engagement from potential power users. Their solution wasn’t just a cool tool for meetings anymore; it became an essential asset for financial advisors struggling to extract crucial financial details from client calls.

However, it’s vital to note that this isn’t the end of the road. Positioning is dynamic, and as they grow and succeed in this niche, there will be opportunities and necessities to adjust and expand their positioning.

Interesting enough, this precise positioning also indirectly aids in attracting additional segments. For instance, even though they are explicitly targeting financial advisors, a legal consultant facing similar challenges might see the value in their product and consider it for their own needs. This phenomenon of attracting peripheral segments happens when your message is so specific and well-crafted that even those outside your target audience can see the potential use case for themselves. It’s somewhat counterintuitive but highly effective, and it's a trend we observe quite frequently with the startups we work with.

Nat: Could you explain the difference between positioning and messaging and why is it crucial for startups and founders to understand it?

Robert: I like to think of positioning as your approach to the market, boiling down to essential questions such as: Who are you building your product for? Who are you aiming to assist, and what exactly are you doing to help them? It’s fundamentally about identifying your market stance, your audience, and the utility of your product.

Positioning operates predominantly at the strategic level. It’s a lot of internal work, aligning your vision and approach. We typically utilize tools like Figma in our workshops to hash out these strategic elements.

Once you’ve solidified your positioning, you transition into messaging. This is about expressing your positioning through various channels, be it in your marketing efforts, sales conversations, or even in the way your product is designed and developed. Messaging translates your strategic positioning into actionable and communicative terms.

Messaging is crucial across all fronts of your startup. You want consistency in how your sales team talks about your product, how your marketing presents it, and how your product team envisions and builds it. Discrepancies in these areas are often signs of poor positioning. You might find each department has its interpretation, leading to a fragmented company image and approach.

For startups, clarity in messaging is non-negotiable. At the early stages, brand messaging can take a backseat. Startups need to prioritize clear, direct communication. Your audience doesn’t know who you are yet; your job is to make them understand and believe in your value proposition quickly and unequivocally. Brand building and nuanced messaging come into play later, once you've established initial success and market presence.

Nat: What are some of the recurring mistakes founders make in these domains? How to avoid them?

Robert: One of the most prevalent issues we observe in startups is the tendency to spread themselves too thin – attempting to be everything to everyone. This pattern is evident in over 90% of the cases we handle. Initially, it was surprising to witness founders, who clearly understood their market, get caught up in this. However, our experience with Fletch provided us with insights into this dilemma.

When something starts to gain traction, the challenge shifts from identifying opportunities to maintaining focus. In our journey with positioning and messaging at Fletch, we encountered requests from clients to expand our services to areas like packaging and content marketing – areas we weren't even targeting. This is similar to a startup’s journey. Take a meeting app as an example; it begins with straightforward functionality but soon starts incorporating features for various use cases, inadvertently drifting into different markets.

From a messaging standpoint, it’s a challenge. In the early stages, founders usually have direct, one-on-one interactions with their target audience, allowing them to communicate the scope of their offerings. This works in a sales call or a personal meeting, but it doesn’t translate well to marketing, where your window of engagement is significantly shorter.

The lack of positioning manifests as an expansive, unfocused message, claiming to be a platform that does everything. This is a red flag indicating a lack of positioning. A well-positioned startup should be able to clearly articulate what it does NOT do.

The cascade effect of this into messaging is profound. Attempting to be all things to all people requires a huge volume of messages to activate a market – a requirement that is often underestimated. Even startups that are on the right track tend to underestimate the number of nuanced messages needed to guide a customer from awareness to purchase and usage.

Addressing this issue head-on requires making tough decisions at the positioning level. If a startup is unwilling to do this, the only alternative is to segment marketing programs extensively, essentially creating separate campaigns for each aspect of the offering. This is often impractical, leading us back to the need for clear, decisive positioning.

Rapid-fire round

Nat: Your biggest regret?

Robert: My biggest regret is not playing college soccer. I had opportunities to play, but at the time, I decided to focus solely on my engineering studies. Looking back, I really miss the game, the camaraderie, and the competitiveness. It’s something I wish I could go back and choose differently, but that decision is in the past now.

Nat: When it comes to creating a landing page, are there any words you think should absolutely never be used?

Robert: The word “everyone.” Whenever I see that word on a landing page, I immediately know there’s an issue. This is especially true for startups. Now, if you’re a gigantic company, a unicorn multiple times over, maybe you can get away with it. Airtable, for instance, used phrases like “build everything” or “do anything” for a while. They’ve managed to establish awareness and define what they do through other means, so they might be able to pull it off. But for most, especially startups, “everyone” and “anything” are red flags and should probably be avoided.

Nat: Do you have a business hero, someone you really look up to in the business world?

Robert: You know, it’s an interesting question. I wouldn’t say I have a specific business hero, but there are definitely a lot of individuals who have significantly influenced my thinking and approach, especially in building Fletch. Jason Fried from Basecamp has always intrigued me. I find myself consistently going back to their blog posts and books. They advocate for a thoughtful approach to business, emphasizing the importance of not rushing, being mindful about who you help, and being passionate about your work. That philosophy has really stuck with me.

Lately, I’ve been closely studying solo content creators, as I'm moving into that space with my partner, Anthony Perry. What fascinates me about them is their approach of building a market before creating a product. I think this is so important, especially for startups, and more should adopt this strategy. Many startups build the product first and then take it to market, which is incredibly risky. On the other hand, building an audience first and then creating a product tailored to them is less risky and provides momentum for different scaling opportunities.

People like Justin Welsh, and even bigger content creators like Mr. Beast with his YouTube endeavors, show the power of this approach. Dicky Bush, and Nicholas Cole with their Ship 30 for 30 initiative are other examples. While I wouldn’t necessarily call them my heroes, they are definitely influencers and have shaped how I think about building my own business.

Nat: If you had the chance to meet 10-year-old Robert, what advice would you give him?

Robert: I’d encourage him to explore and embrace his curiosities, and immerse himself in learning about things that captivate his attention. Later on, once he has a solid grasp of his passions and strengths, he can then shift his focus to aligning these with what the world values.

In a way, it’s like conducting a personal positioning exercise, identifying where your innate interests meet the market’s needs. This alignment not only leads to professional success but also ensures a fulfilling and engaging life journey.

So, to sum it up, I'd advise 10-year-old Robert to be true to himself, chase his interests relentlessly, and trust that this path will eventually lead him to find his unique place in the world.

Get to know Robert.