This article draws on my experience as an interim CMO and board adviser, working with leadership teams on how go-to-market strategies are built, tested and sustained in complex organisations.
Introduction — Designing Systems That Learn Before They Scale
Most go-to-market strategies fail long before a campaign is launched or a sales target is missed. They fail at the moment organisations decide how they will learn.
In strong product organisations, learning starts cheaply and early. A wireframe is tested before a platform is built. A workflow is observed before a process is automated. Users are watched. Buyers are questioned. CIOs test integration. Analysts challenge assumptions. Each perspective exposes a different risk.
The purpose of this early work is not validation. It is design. To understand not only whether a product works, but who it is really for, which problem it truly solves, how people actually decide under uncertainty, and which problems have not yet been considered.
Many organisations reverse this sequence. They build first, scale early, and ask the market to explain what they have already created. At that point, go-to-market becomes an exercise in interpretation rather than design.
This article sets out a simple argument. Durable growth is built by designing learning systems first, and go-to-market systems second. Speed matters, but how you grow matters more than how fast.
Why Innovation Must Be Disciplined by Behaviour and How People Decide
True category creation rarely begins with an idea. It begins with a deep understanding of how people behave, how they make decisions under uncertainty, the context in which they work and live, and the frictions that shape what they adopt, delay or resist.
Buyers are rarely explicit about what they want next. But their behaviour is not random. It reveals constraints, workarounds, unmet needs and latent pain points. The most successful innovators do not ask markets what to build. They observe how markets behave, infer what could be better, and design experiences people did not explicitly request but immediately recognise as right.
Strong innovation is built on insight, not separated from it.
Where many organisations go wrong is not in ambition, but in sequence. Strategy formation is often driven by a product idea and internal revenue targets, growth models and financial expectations long before buyer behaviour has been properly understood. Product concepts are agreed, go-to-market direction is fixed, and only then tested against the market.
When this happens, product–market fit is asserted rather than proven. The buyer becomes vague. Targeting becomes broad. Segmentation becomes generic. These are not root causes. They are symptoms of upstream uncertainty about who the product is really for and why it should exist.
At that point, marketing is asked to bridge a gap that should never have existed. Marketing is asked to create belief. Interest can be created; advocacy cannot, and reputation is put at risk.
Sales then becomes the shock absorber for weak product–market fit. Experienced sales leaders hunt the few buyers who might fit. They use credibility and relationships to close early lighthouse deals and influence product upstream. This is not product–market fit. It is relationship-driven substitution that distorts the product and puts the customer at risk.
Two or three quarters later, the pattern changes. The addressable pool is exhausted. Repeatability fails. Advocacy does not emerge. What looked like execution failure is revealed as a failure of product–market truth.
When Strategy Embeds Before Understanding Matures
When product–market fit is weak, the next failure is rarely technical. It is epistemic: a failure in how organisations decide what they believe to be true about their market.
Most organisations do not lack data. What they lack is the time, discipline and permission to interrogate it properly before strategy hardens. Under pressure to move quickly, leaders compress the period in which strategy is formed. Product concepts are agreed, revenue targets are set, and go-to-market direction is fixed before market understanding is mature enough to carry that weight.
When marketing is not given access to the full product business case, underlying research or buyer interviews, propositions are written from partial documents and verbal briefings. Expectations are high, but insight is thin.
The consequences are predictable. Buyer understanding becomes generic. Personas converge. Segments blur. More damaging still, organisations begin to describe themselves to the market in the same way they describe themselves internally. Business unit structure becomes customer narrative. Product architecture becomes value proposition. Internal organisation design quietly becomes external communication.
This is how internally coherent strategies become externally opaque.
Over time, data that might have challenged the narrative is rarely collected rigorously. It becomes anecdotal or operational, owned by delivery rather than by strategy. By the time meaningful signals appear, they arrive as problems to be managed rather than inputs that could reshape direction, and strategy is defended rather than evolved.
In high‑performing organisations, leaders deliberately interrupt this drift. They pause execution and ask a small number of hard questions: what have we learned since we last made a major commitment, which signals matter most now, what are we missing, what should we adjust immediately to improve our ability to convert opportunity faster, what is holding us back, and how do we solve this together. These moments of collective interrogation are where weak signals become strategic inputs, rather than operational noise.
When Communication Exposes Fragile Foundations
When product–market fit and the proposition are unclear or still evolving, communication is often where the fragility of the go-to-market strategy first becomes visible.
Marketing is asked to embed a brand story into a system that does not yet have firm foundations. The product is not clearly chosen by the market. The proposition is still forming. The brand is not well known. Differentiation is thin. Distinctiveness is hard to sustain.
Instead of expressing a clear choice about who the product is for, which problem it solves and why it is genuinely different, communication becomes an attempt to hold together several unresolved questions at once. It explains more than it differentiates, and often sets expectations the product cannot sustain.
Buyers are left to do the work of interpretation themselves. The burden of targeting is pushed onto the audience rather than carried by the organisation through precise segmentation and deliberate choice. Over time, sales compensates. Good salespeople simplify, reinterpret and personalise what marketing produces in order to make it usable. Every strong performer carries a slightly different version of the story.
This is not a failure of creativity. It is a sign that the go-to-market system is asking communication to solve problems that belong upstream, in product–market fit, proposition design and strategic choice.
When Execution Evolves Faster Than the Proposition
When the proposition and go-to-market design are fragile, execution gravitates towards what is easiest to control: activity.
Organisations still have revenue to generate, development costs to recoup, innovation to demonstrate and market perception to uphold, even when the proposition is not yet fully formed. In that context, go-to-market teams are forced to create something usable. They write propositions, shape narratives and launch campaigns because doing nothing is not an option.
In this environment, another risk quietly emerges. As teams respond to individual deals, implementations and customer demands, the product proposition itself begins to evolve without centralised agreement or deliberate recalibration. Features are added, services are adapted, commitments expand, and the proposition shifts deal by deal.
This does not only affect future go-to-market design. It reshapes the live pipeline. Sales sells one version of the product, delivery implements another, marketing continues to describe a third. Over time, the organisation is no longer scaling a single proposition, but several slightly different ones at once.
In the busyness of execution, there is little time to pause and recalibrate. Testing becomes tactical. Feedback loops are internal. Insight accumulates in fragments. Communication struggles to evolve. Messages repeat. Campaigns rotate. Narratives remain static until the next product release provides something new to say.
Without protected time and investment to interrogate what is being learned, communication stops becoming more precise, more differentiated and more credible. Scale increases, but understanding does not.
When Market Advantage Is Won or Lost
Once a new product, service or business line is in market, the quality of learning matters as much as the quality of design and launch.
Sales learns from which deals convert and which stall. Customer success learns where implementations struggle. Product learns which features are adopted. RevOps sees patterns in cycle length and leakage. Win–loss data should be one of the richest sources of insight, yet it is often sanitised. Losses are attributed to price or competitors when the real reasons are more human: timing, trust, readiness and fit.
In well‑oiled organisations, these signals are not simply collected, they are deliberately integrated. Commercial insight is treated as a shared asset, not a functional by‑product. Leaders design regular forums, deep dives and joint reviews in which sales, product, marketing, customer success and operations are expected to bring evidence, not anecdotes, and to test each other’s assumptions against what the market is actually doing.
Where this discipline is missing, collaboration happens opportunistically rather than systematically. Insight remains partial. Strong signals are diluted by opinion. Weak signals are missed altogether. Strategy is at risk of being shaped by fragments rather than by a coherent view of reality. Weak signals are also often inconvenient. They challenge prior decisions, investment cases and personal credibility. In many organisations, it is easier to defend momentum than to reopen direction.
As a result, strategy is at risk of being shaped by partial signals. Functions optimise locally rather than integrating insight deliberately.
Firms that progress fastest make collaboration a leadership discipline. They require robust, comparable inputs across functions. They insist on qualitative depth and quantitative rigour. They create the conditions in which collective judgement improves over time.
They fail not because they lacked data, but because they did not take learning seriously enough, early enough, while there was still time to shape category position and market advantage.
When How the Organisation Learns Determines How It Grows
Organisations talk endlessly about learning and development for people. Very few apply the same discipline to how the organisation itself learns.
Product, operations, sales, marketing and customer success all generate rich signals. The failure is not gathering them, but making sense of them together. Enterprise sales cycles run for years. During that time, products are tailored, delivery complexity grows and customer needs evolve. Left unchecked, this creates drift.
Leading firms design collective calibration points explicitly. They create forums where functions interrogate the same signals, agree what has changed and decide what to test next. They treat go-to-market not as a coordination problem, but as a continuous cross-functional learning opportunity.
When How You Grow Matters More Than How Fast
Every leadership team faces the same tension. Pressure to move quickly competes with the need to stabilise revenue and protect reputation. Pressure to show momentum competes with the need to listen carefully to what the market is actually saying.
Senior leaders are not only deciding when to push forward and when to pause. They are also deciding whether the organisation has built the internal learning systems required to move safely, whether insight can flow fast and be objectively understood across functions, whether weak signals will be seen early enough, and whether the organisation can adapt without damaging revenue quality, customer trust or brand reputation.
The organisations that build durable market positions are those whose leaders intervene early, protect learning when revenue pressure is high, and are not afraid to return to the proposition itself to rewrite it and upgrade the go-to-market design. They recognise that course correction is rarely resisted because of evidence, but because of careers, capital already committed and the discomfort of revisiting decisions that were once publicly endorsed.
In the end, go-to-market succeeds not because organisations move fastest, but because leaders design systems that allow them to move with speed, judgement and control at the same time.
About the Author
Kaila Yates is a board adviser and interim Chief Marketing Officer working with technology and financial services organisations on growth, go-to-market design and marketing transformation. Through Two Jacks Communications, she supports boards and executive teams to design learning systems, govern growth and build go-to-market strategies that scale without losing their way.
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