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  • Writer's pictureMatheus Reis

B2B Startups and the Failure of Building Sales Motions Before Product Market Fit

Updated: Apr 4, 2023

I want to deconstruct this complex topic and make some analyses, as I'm constantly seeing a common pattern of B2B/Enterprise companies that haven't reached product-market fit and decided to scale their sales motion with heavy investments in sales and marketing.

While the strategy doesn't end as expected, there is an intense discussion of who is responsible for failing the company's success. When actually, there is a deeper organizational issue that makes this strategy not successful most of the time.


TL;DR — Sales incentives and short-term traps motivated by singular metrics, conflict with unbiased market validation. By doing it at this stage, B2B/Enterprise companies can end up with organizational scars damaging a long-term plan for success. Being humble and honest about the product moment, onboarding the team in the same direction and making them comfortable with hard decisions, understanding the market by industry segment, adopting a scout strategy for sales, and a pragmatic product development approach can increase their chances of finding product-market fit and growing the business.


Imagine this hypothetical scenario;

A B2B/Enterprise product with a value proposition missing market validation, no detailed and deeper information on customers' needs, positioning vs pricing challenges, lacking real usage data to prove ROI, and no awareness of segment specifications and needs such as integrations, regulations, or use cases. It's a common raw product missing its foundations to pursue product-market fit.

With this high-level concept, no view on target segments, effectiveness, pricing, competitor comparisons, system requirements, and ROI, because all of it is just a vague guess so far, the Enterprise sales motion starts spinning and bringing prospects to the funnel.

Marketing campaigns are set. Normally trying to copycat competitors' buzzwords, but fail in defining a good demographic setup. With the company's mission of revolutionizing the industry, and lacking further customer knowledge depth, the communication strategy tends to be as broad as this statement.

Sales start digging the market in search of validated prospects. With the pressure to hit quotas, a board of investors to be accountable for, and lacking the foundation for a systemic validation process, there are great chances of those first prospects being early adopter outliers, that reacted well to the high-level concepts.

As soon they are pushed to close the deal, these companies raise a set of segment-specific needs, and fastly the backlog starts increasing. Every new company at the door makes a set of questions and demands, all translated into urgent deal-breaker feature/action requests.

The product team has to run to commit or provide detailed feedback to every single one of them, even knowing most of those initiatives will cool down due to not-yet-know organizational, financial internal situations. But in the end, numbers slowly start to move and even a sentiment of product-market fit may emerge.

Until the reality comes through.


Typically, B2B contracts are annual, so after 9-12 months, churn rates tend to skyrocket for the few customers that converted. But now leaving the company with serious organizational scars, such as:

  • A reactive product team, with the need for top-down decisions to dictate and push meaningful progress.

  • A demotivated tech team, that after being thrown into different projects without meaningful results, start perceiving it as a company without focus.

  • The customer success team becomes overloaded with operational tasks to compensate for an unfinished product, unable to support customers' journey into a systematic value delivery process.

  • The marketing operation bleeds resources while suffering to deliver an appealing message to the market, when not trying to mask it by boosting vanity metrics.

  • While the sales team struggles on defining strategies as they cannot build rapport with their ideal customer profile, often failing to hit their quotas. If they ever hit it at all.

In the end, this tends to lead to a dysfunctional revenue operation, that ultimately has a hard time bringing in new customers and retaining existing ones. Those who have been in a scenario like that before, probably have heard something like:

  • "We need more seniority in the product team because the current one is not being able to prioritize correctly our customer's needs."

  • "Sales team has to do better validation, they are pushing wrong prospects because they only think about their quotas."

  • "Customer success is not being strategic enough. They are focusing too much on operational tasks for their customers instead of managing their expectations and growing accounts."

  • Or even customers get the fault with phrases like " we need to educate our customers, they don't know what they need."

And the complaint list goes further on everyone trying to point fingers on who to blame and forget that perhaps there is a much deeper issue causing this effect.


What can go wrong by focusing on scaling sales before reaching product-market fit?


Sales Economics Conflicts with Unbiased Market Validation

It's commonly believed that the sales team, for being the "point of the spear" in the market, is best positioned to grow the company's knowledge of its ideal customer profile. But that is not totally right. Even though their ability to engage in questions to understand their customer is a shared skill with product managers, the economics behind the expected outcomes diverges from their product peers.

Market discovery is a learning process that aims to identify a problem that repeatedly occurs in a specific group. With an exploratory approach, you should be looking into things like identifying what pain points concern your customer, validating if your assumptions about their reality are right, if any segment incentives are influencing the context, suitable workarounds, and getting an understanding of the impact of the problems' resolution.

Product managers use validation interviews to iteratively explore customers' objections. The expected outcome is being able to collect a deep understanding of it to define a clear problem description. For then be used in collaboration with the development/design team to propose solutions. Or to learn the problem is not worthy enough to bother looking into it.

On the other hand, skilled salespeople aim to anticipate potential blockers, minimize issues, mitigate objections, and address concerns by having well-positioned responses at the ready. All of it, with the ultimate goal of guiding that unique prospect through the sales funnel. Their discovery process It's designed to maximize their chances of winning the customer's signature, not to circle on top of a challenge to understand its root causes.


If an Enterprise Startup scales its sales team too early, it may not have the necessary well-defined understanding of its customers to support closing deals. For that reason, sales teams will rely on early adopter outliers – those who respond well to abstract views of value delivery during the validation process.

However, as sales push forward to close deals, the need for more definitions arises from prospects. And they are plenty, ranging from product changes to building collateral that better defines use cases, as well as the creation of imaginary ROI calculations for different market verticals. Additionally, involving a significant organizational effort to comply with quality/security market standards, which often is implemented ahead of time.

Although those requests may seem valuable and qualified product feedback, it comes from non-paid customers, leveraging on their high annual contract value potential to narrow a broad definition into their specific needs. This often comes as urgent deal-breakers stopping them to sign the contract, where the motivation behind it is not clear, normally relying only on the possible revenue contribution. This will force the product team to halt a more systematic discovery process to focus on them, dashing any chances of establishing a significant decision-making system for prioritization.


Falling into short-term wins traps

A misunderstanding that revenue is the only sign of product-market fit can lead executives to push for short-term wins. As things start to lose control, as a remedy, those same executives will intensify top-down decisions as a way to stabilize things on their own.

And situations like these will be recurrent, whatever the executive position is:

  • The board indicates a company from an unexplored segment, and the contract gets tied to a set of customized segment-specific functionalities. The CEO agrees and commits to "oversee" the process. "Let's do whatever it takes to make it look good for the investors".

  • An Enterprise is running a free PoC, promising to affect revenue significantly. Due to unexpected implementation issues requiring additional functionalities, PoC is delayed. The Director of Sales has taken charge to guarantee demands will be met. "We need to convert this PoC, this deal will be a game changer".

  • And an old customer is threatening not to renew if their list of features request is not delivered that quarter. The Director of Customer Success gets personally involved to "ensure they will be prioritized".

Normally motivated by bringing revenue or optimizing their own functional KPIs, executives put their energy into pushing on feature delivery rather than discovering the root cause of customers' pain points and how it reflects the market they're trying to conquer.

So now the political games of prioritization start. Product Managers who should be focused on discovering and validating customer needs, by establishing a pragmatic approach to diverge and converge hypotheses, will be forced to deal with internal competing interests in delivering features.


Both situations deviate the company from what should be its main goal.

Indeep market discovery should be the main company' priority during pre product-market fit.

Instead, these mistakes dilute the attention by directing organizational efforts toward solving internal roadblocks. While the focus is set on the adjacent process of acquiring and retaining customers, because that is what good companies do, it misses the main point of the current stage. The team should prioritize understanding the root causes of their customers' pain points well enough to offer a solution to solve them. It's a long-term winning game. Without product-market fit and a clear ICP definition, those deliveries tend to be just another guess, driven by individual metrics such as revenue.

Since there is no one rule to success, I cannot say what may work for you and your company to succeed at this stage. But surely there is a set of actions and behavior that if neglected, can increase the chances of failure.


Be humble and honest about your product readiness

Founders may mislead about product-market fit and production readiness as an attempt that by leading the company to act as they have it, PMF will become a reality, or thinking they can push the pre-PMF problems away. This misleading can happen from different sources, such as thinking that fundraising or isolated metric analysis without explaining its context are signs of it.

Things can get worst if followed by cultural restrictions on who is "allowed" to speak on the customer's behalf, permitting just a group with a set of knowledge or credentials for it. Additionally, lack of acknowledging customer metrics such as churns, and paybacks/LTV, which often come with internal barriers to getting access to those numbers.

Being conscientious about the current situation and onboarding your team to work as a unit to overcome product-market fit is much superior to the imaginary frustration executives tend to think their team will have by working on a non-complete product.

The phrase "Fake it until you make it" doesn't work on those "making it".

Align the company towards the same objective and make them comfortable with hard decisions

The success of an early-stage product cannot be reduced to a singular metric, requiring the company to pursue initiatives across different business aspects. Since each function has its core responsibilities, they may compete for the company's priority, based on their perspectives and needs. When conquered, executives tend to push the improvement of their respective KPIs to ensure accountability.

This cause-and-effect factor impulsions departments to prioritize their internal optimization instead of pursuing the main goal of identifying validated signs that they are solving a customer pain that reflects the need of that market.

The focus on scaling functional operations will clarify after product-market fit, when on a positive unit economic perspective, new customers arrive, unrelated to your acquisition efforts, and the ones using it, are eager for more. In this context, there will be an increased demand for an established and efficient experience at every touchpoint. Shifting the company from the previous framework of "what should we build" to "ensure it doesn't break".

This is why there may be a sentiment about reaching PMF in my hypothetical story. Some numbers are moving up, areas are struggling and things are breaking, which can give you the sentiment of the need to scale. But is often an organizational failure in identifying value delivery, it's not about efficiency yet.

To secure better cross-functional cohesion and collaboration, OKRs have gained popularity nowadays because they help align each department with a singular strategy. Use what fits you best, as long your team can commit to the same direction, and you can measure it.

A key indicator of organizational alignment is the ability for individual decisions reach consensus on difficult trade-offs.

When faced with limited resources and competing interests, prioritization can be an organizational challenge. The same can be true when evaluating market opportunities. Both cases require the company to be in sync with what they should focus on first, even though it means giving away a great opportunity, postponing a project, or letting a non-fit customer go. For a startup to achieve operational maturity, it becomes essential to establish a cohesive culture that fosters a shared vision of the company's direction. It creates easier times for conflict resolution and prioritization.


Segment your market, learn from it, and conquer them

While it's ok to define a company's mission by stating broad approaches such as:

"Changing the way [Recruitment/Payments/Logistics/Data Science/{choose yours}] is done."

When describing the strategy to achieve its mission, it's crucial to be specific. By following the well-known mantra of "putting the problem first", companies will identify nuances in different markets.

The value proposition of enterprise products typically aims to abstract a process to deliver better efficiency in a one-fits-all solution. It's important to notice that those processes can be heavily influenced by the industry segments in which companies operate. Factors may include unique regulations for a particular industry, market dynamics, or even consultancies promoting enterprise organizational structure projects

As a result, companies may use different software solutions, face varying market regulations, adopt different supply chain strategies, suffer from different organizational pressures, and deal with different levels of market maturity.

By seeing the market through a segmentation lens, B2B companies can obtain a better understanding of their customers' unique needs and challenges. A detailed ICP definition improves the product strategy, which is an essential piece for day-to-day prioritization. In a B2B relationship, the value of individuals and accounts can be significant due to factors such as logo attractiveness, investors' interests, or internal power dynamics, where a single executive may hold considerable influence over a project. By having a strong strategy in place, you can better navigate through potential deviations in the direction of your product vision.


As you may have realized by now, the company's strategy at the early stage should be intrinsically related to the product strategy itself. Therefore, the knowledge you acquire to build your product will create the foundation for other departments to build their functions.

From a business perspective, segmentation allows companies to optimize their go-to-market efforts by tailoring their messaging on how their solution can be leveraged on the segment's specific pain points, positively impacting conversion rates. From a product perspective, by recognizing common vs specific requests, companies better prioritize their efforts, keeping a focused strategy. As a result of a more effective product, customers tend to be more loyal and advocate more for the product.

Finally, from an economic perspective, it enables companies to identify promising use cases for their products, providing them with qualified insights to demonstrate the economic viability of their products to customers, through ROI. Overall, by adopting a segmentation-based approach, B2B companies can build a more effective strategy.


Use Sales as your scout, not your closer

Rather than simply trying to close deals, the sales team should act as scouts. Positioned as a strategic partner in your journey to achieve product-market fit, their bias will be aligned towards learning and rejecting wrong hypotheses.

To do this effectively, acquisition strategies can be shaped according to the Roger Adoption Curve, which describes the behavior of acceptance of new ideas through five stages. Innovators, early adopted, large majority, and late majority. At this stage, you are better suited with innovators – customers who are facing a problem that is so damaging to their business that they are willing to take on high risks to find a solution, even for the price of paying to use an unfinished and rough version of your product.

Be aware that open innovation programs from enterprises tend to hype technological trends and advocate the central problem as the "lack of innovation" itself. This can result in poorly designed programs that incentivize the adoption of technological innovation as a core solution, rather than focusing on framing organizational problems that need to be solved.

Even though they seem attractive and more open for startups, with a simplified buying process, and pre-approved budget for PoCs, they often have a hard time matching your value proposition with real interests and needs. Although it can look like a safe learning sandbox, ensure your solution is aligned with the company's needs before investing significant time and resources.


To design this operation, start by pairing a strong discovery salesperson with the product team to work on a structured validation process. A questionnaire, for example, can be a useful tool to identify customer problems, motivations, and root causes. This step is crucial to filter as many wrong prospects as you can. A wrong customer will perpetuate a leak-bucked effect, disturbing your product strategy and consuming a lot of internal resources.

At this stage, your sales collateral should demonstrate that you understand the problem your prospects are facing and showcase clearly how you will solve it. The 7-slide deck you build to secure investment is not going to work. Prospects are primarily interested in finding a solution to their issues, not in the founder's history or market potential. Be agile in your sales approach by iterating with prospects and refining your pitch about wrong assumptions or missing details.

Change the compensation structure to incentivize leading prospects to product demos, such as Trials and PoCs. This will encourage sales to support the company in testing hypotheses rather than closing. However, it's important to ensure that these demos are not self-served and that a more high-touch process is in place, involving different teams such as CS, PM, UX, and Devs. By creating a concierge test experience and shadowing the user as much as possible, you can obtain valuable insights into how customers intend to use the product to solve their issues.


Be Pragmatic in your Product Strategy

When it comes to execution during the pre-product-market fit phase, you have to be pragmatic. Often I see too much focus on perfecting the process, tools, and techniques while neglecting the essential part of the job, which is to provide value as the outcome. Understanding the objective of scaling a product operation is to maximize how many "tries" can be done, instead of focusing on mastering every individual one, is going to be the difference between creating value instead of bureaucracy.

There are some activities to consider for your product development cycles, where the main objective is to be as effective as possible to put your hypothesis to the test and collect feedback to adjust the course of action.

  • Brainstorm with your team

Building a roadmap is a collaborative effort, and during the pre-market fit, should be the company's mission to pursue it. Product leads are responsible to deliver it, not dictate it.

  • Encourage and engage your technical team

They are the main gear of product development. Promote it and reward them to be involved in discussing what should be built.

  • Establish a decision process

Apply a logical process to evaluate your decisions. It reduces bias and onboards others on the same point of view.

  • Prioritize based on product vision & strategy

The product vision is your north star, and the strategy is what to do to get there. Avoid half-done features pailing up after every new input you receive.

  • Write specifications

Write down requirements, and acceptance criteria to align what outcomes you expect, that can be measured.

  • Don't over-engineer

Focus on building 90/10 solutions. Think of what gets you 90% of the solution with 10% of the effort.

  • Agree on deadlines

Defined cycle lengths help establish a motion of progress with development, delivery, and learning. Most software development projects fit well with agile methodologies.

  • Set SMART goals

Guide your cycles with meaningful outcomes. SMART goals are Specific, Measurable, Achievable, Relevant, and Time-Bound.

  • Talk to customers

You shouldn't be busy enough to not talk with them. Even in moments when you are focused on complex/technical challenges with your team, discovery should be at the core of your function. Make it "business as usual".

  • Collect feedback

A data-driven operation means that qualitative and quantitative information is the center of your intel to determine if your product works. Build dashboards, reports, and analytics.

  • Share customer data

Avoid silos of data. The metric definitions should be unique across the company, and once selected, everyone should have access to it, and to customers as well.

  • Structure a product council

Gather internal customer representatives to discuss customer problems and solutions. If possible bring customers to share the use cases too. It will ensure they are bringing their learning, and returning to their functions with aligned new inputs.

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