The GTM Doctor's Diagnosis: Why Your Strategy is Perfect But Your Execution is Killing You | Dinuka Wijesinghe | S6 E9

Written by Mike J Midgley | Nov 10, 2025 9:00:52 AM

Welcome to the Force & Friction Podcast, where we break down what really moves the needle in GTM, RevOps, AI, partnerships, and SaaS growth. Today, we're joined by Dinuka Wijesinghe, the GTM Doctor and founder of Serendum Strategies.

With a PhD in astrophysics and six years of experience mastering go-to-market at scale at Google, Dinuka brings a unique blend of academic rigor and practical, in-the-trenches experience.

He shares his core thesis: when it comes to go-to-market, execution matters even more than strategy.

We dive deep into why even the most brilliant strategies fail, the critical difference between companies that execute well and those that don't, and the lessons startups can learn from giants like Google.

Dinuka Wijesinghe

Dinuka Wijesinghe is the "GTM Doctor" who combines scientific methodology with practical go-to-market expertise to help Seed-Series

A B2B SaaS technical founders scale from good products to great businesses. With a PhD in Astrophysics and 6 years at Google, he brings both analytical rigor and proven GTM experience to the startup world.

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Here are the core areas we discuss in today's episode:

1. The Technical Founder's Dilemma: Building a Product vs. Building a Business

Dinuka opens the conversation by highlighting a common pitfall for technical founders: the belief that if you build a great product, customers will automatically come.

He argues that this mindset fails to recognize the fundamental difference between building a product and building a business. While technical founders are often brilliant at product development, they can struggle with the commercial aspects of go-to-market, such as customer discovery, messaging, and sales.

This can lead to years of wasted effort and investment, with little to no market traction.

"I've worked with so many founders right now, and I just start seeing these trends of what people are good at, and what people aren't good at when they start building a company. And they go in, especially for technical founders, who are generally very smart, very ambitious, and they start off believing that, you know, you build it and they will come. And after a couple of years, many of them start realizing that they have not come yet. And it's just because there's two different skill sets, right? There's the skill set of building the product itself, but then the skill set of building a business around it. And so a lot of for a lot of founders that I work with, I tell them that, you know, you're not building a product. You're really building a business, and the product is just one part of that."

Dinuka's experience underscores the importance of a holistic approach to building a company, where go-to-market is not an afterthought but an integral part of the strategy from day one.

He advises founders to either develop their business acumen or bring in partners who can fill that gap, ensuring that the company is not just building a great product, but a sustainable and scalable business.

2. The Perils of Disconnecting from the Market: VCs vs. Customers

A recurring theme in the conversation is the critical importance of staying connected to the market and listening to the voice of the customer.

Dinuka warns that founders, particularly those who have raised significant funding, can fall into the trap of prioritizing the demands of their investors over the needs of their customers. This can create a vicious cycle of building features that no one wants, leading to a lack of traction and a dwindling runway.

"And a lot of the time, what I do find is that, especially if founders, you know, raise a lot of money, their perspective changes towards what the VCs want versus what the market wants. Right? And so VCs have a very particular point of view, but they're not the buyers, usually, of your product. And so sometimes founders, it creates that area of friction as well, because they don't want to, you know, make their investors angry, and at the same time, they have a bias towards building, and so it just all creates this vicious cycle of staying away from the market, staying away from their customers."

He emphasizes that the most successful founders are those who are constantly in the market, speaking to customers, keeping an eye on the competition, and adapting their strategy based on real-time feedback.

This customer-centric approach is not just about gathering requirements; it's about building a deep understanding of the customer's world and using that understanding to guide every aspect of the business.

3. Strategy vs. Execution: Where the Go-to-Market Game is Won and Lost

Dinuka's core thesis is that an okay strategy with great execution will always beat an excellent strategy with average execution. He argues that while a well-crafted strategy is important, it's the consistent and systematic execution of that strategy that ultimately determines success.

Companies that excel at execution are those that have a clear, integrated plan where every team understands their role, and they are constantly experimenting, learning, and iterating based on market feedback.

"But really, the game is won and lost in the execution. An okay strategy with great execution will always beat an excellent strategy with average execution. And the reason for that is that when you execute, and execute consistently and systematically, you will be able to get feedback from the market much faster, and then you'll be able to incorporate that into your build."

He breaks down effective execution into three key components: integration (ensuring all teams are aligned and working towards the same North Star), operationalization (building the systems and processes to enable consistent execution), and experimentation (creating a culture of continuous learning and improvement).

This framework provides a practical roadmap for companies looking to bridge the gap between strategy and execution.

Download the The 5-3 GTM Framework PDF Here: The scientific approach to successfully go-to-market & win with your product

4. The Power of ICP Profiling: A Data-Driven Approach to Go-to-Market

One of the most actionable insights from the conversation is Dinuka's approach to Ideal Customer Profile (ICP) profiling. He advocates for a data-driven, tiered approach where potential customers are scored and prioritized based on their fit with the company's offerings.

This allows for a more targeted and efficient go-to-market motion, where the right message is delivered to the right audience by the right person.

"But if you start with a hypothesis and execute that, you'll very quickly know if that ICP that you built as a hypothesis is working or not, and then you can refine it. But if you don't, then you'll just get a bunch of mixed messages, mixed data bits, and you start to latch on to something that confirms your existing biases. Be like, oh yeah, I knew this feature was gonna work. Two customers, like, said, this is great. No one's paid yet, but they said it was great. We don't know anything about those customers, why they liked it, why they wanted it."

This methodical approach to ICP profiling not only improves the efficiency of sales and marketing efforts but also creates a powerful feedback loop for product development.

By understanding which customers are the best fit and why, companies can prioritize their product roadmap and build features that truly solve the needs of their most valuable customers.

5. The Three Pillars of Entrepreneurial Survival: Pain, Uncertainty, and Failure

In a candid and insightful closing, Dinuka shares his belief that there are three essential ingredients for entrepreneurial success: the ability to tolerate pain, uncertainty, and failure. He argues that in today's rapidly changing market, these are not just unfortunate side effects of the entrepreneurial journey, but necessary prerequisites for survival and long-term success.

Founders who can withstand these challenges are the ones who will ultimately be able to adapt, innovate, and build resilient and enduring companies.

"There are usually 3 things I think you need to succeed, without which you just cannot, I don't think. The first… and there are… it's an extreme tolerance to pain, Uncertainty, and failure. Right? And the longer you can tolerate that at extreme levels, the higher the chance of success. Everything else you learn, you can figure out, but you just need to be able to withstand that for extended periods of time, and unfortunately, it's just gonna be like this for the foreseeable future."

This is a sobering but essential reminder for any aspiring entrepreneur. The path to success is not a straight line; it's a winding road filled with obstacles and setbacks. But for those who have the resilience and determination to persevere, the rewards can be immense.

Final Thoughts:

Dinuka Wijesinghe's insights are a masterclass in the art and science of go-to-market. His emphasis on execution over strategy, his data-driven approach to ICP profiling, and his candid assessment of the realities of entrepreneurial life provide a powerful and practical guide for any founder or business leader looking to build a successful and sustainable company.

Where we are all faced with constant change and uncertainty, his message is clear: the companies that will win are those that can execute with clarity, consistency, and a relentless focus on the customer.

Check out more at Serendib Strategy Website

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Mike Midgley runs a portfolio career, a dynamic hands on digital entrepreneur, founder of the Scrubbing Squad, NXD, strategist, public speaker, Winning by Design certified Revenue Architect and Host at The Force & Friction Podcast.

Mike has achieved multiple exits over a 30+ year career, raised Venture Capital and franchised his businesses 68 times.

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