With over 15 years of experience in in-house and consulting with and for B2B SaaS and cloud technology companies, we are well placed to understand that they face intense go-to-market (GTM) challenges as they grow.
GTM encompasses how an organisation delivers its product to market and drives revenue, spanning sales, marketing, product, and customer success. As companies transition from scale-up (high-growth post-startup phase) to enterprise-level, they encounter new obstacles arising from rapid growth, increasing complexity, and fierce market competition.
Many of these challenges are cross-functional, requiring tight coordination between teams. This report analyses the biggest GTM challenges in the UK and USA for scale-ups and large enterprises, highlighting recurring themes, root causes, and differences between growth-stage and mature companies. Examples and case studies are included to illustrate key points.
In today’s saturated B2B tech markets, both scale-ups and enterprises struggle to stand out. Heightened competition and empowered buyers force companies to sharpen their GTM approaches:
Hyper-Competitive Markets & Differentiation – Established incumbents and new entrants crowd most SaaS categories, turning the market into a “gladiator arena”. Breaking through the noise requires a laser-focused value proposition and deep understanding of the ideal customer profile (ICP).
Scale-ups often battle to establish credibility against larger rivals, while enterprises must fend off agile startups eroding their market share. For example, in the CRM space crowded with lookalike solutions, Zoho succeeded by targeting SMBs with a lean, affordable offering. In contrast, Salesforce focuses on large enterprises that need robust customisation. At the same time, HubSpot leveraged its marketing platform to enhance its CRM value proposition—a perfect example of each honing a distinct value proposition to differentiate in a packed field.
Evolving Buyer Behaviour & Longer Sales Cycles – Modern B2B buyers are highly informed and conduct extensive research before engaging sales. The traditional linear sales funnel is effectively “dead” – today’s buyer journey is a non-linear maze. Buyers in the US and UK often self-educate via content, peer communities, and trials, meaning GTM teams must engage prospects with value-added content marketing and thought leadership early on.
Decision cycles have grown longer and involve more stakeholders, especially in enterprise sales. In the UK and Europe, customers tend to have even longer sales cycles and demand greater trust and transparency upfront. This shift challenges marketing to provide the right content at the right time and sales teams to guide prospects through complex decision processes rather than simple funnels.
Rising Customer Acquisition Costs (CAC) – Reaching target customers has become increasingly expensive amid crowded digital channels. Many traditional tactics (e.g. untargeted display ads) have lost effectiveness.
Customer acquisition cost (CAC) is soaring in competitive markets, squeezing ROI on marketing spend, and is a serious concern for scale-ups with limited budgets and enterprises seeking efficient growth. As a result, companies are adopting more targeted, cost-efficient GTM tactics. Account-based marketing (ABM) is one such strategy, focusing resources on high-value accounts with personalised outreach to improve conversion rates and ROI.
Scale-ups must often get creative (leveraging viral product-led growth, communities, or partnerships) to acquire customers cost-effectively. At the same time, larger firms diversify channels and invest in brand to offset ad saturation.
A 2025 industry analysis noted that in saturated markets, “distribution mastery trumps product features” – the winners are often those who execute GTM exceptionally well via creative marketing, strategic partnerships, and community engagement.
Global and Regional Market Nuances – Companies expanding between the USA and the UK/Europe face additional GTM hurdles. A US scale-up entering the UK/EU market might need to adjust to strict data regulations (e.g. GDPR compliance) and localise its messaging and pricing to regional expectations. Likewise, UK SaaS firms aiming to scale in the US encounter a larger, highly competitive landscape and may need significant marketing investment to build brand awareness stateside.
Adapting to regional buying behaviors and regulatory requirements is a key part of GTM strategy – for instance, ensuring product features and support meet local needs and compliance standards (as US companies must do for EU GDPR). These nuances add further complexity to marketing and product positioning, and failing to address them can stall international growth.
Rapid growth and organisational complexity pose internal GTM challenges that can derail execution if not managed. As companies scale, cross-functional alignment and efficient processes become critical:
Organisational Silos and Misalignment – As teams grow larger, it’s common to encounter silos between departments, unclear responsibilities, and conflicting priorities. Misalignment between sales, marketing, product, and customer success can severely hinder GTM execution. For example, sales and marketing disconnects often lead to wasted leads or inconsistent messaging – a known GTM failure point.
Enterprise organisations, with their many specialised roles, often struggle with siloed data and communication gaps that stifle agility. Scale-ups, despite smaller teams, can also suffer misalignment as they add new functions or expand globally. Ensuring all GTM functions stay “on the same page” with a shared vision and feedback loop is challenging but vital.
One case study (TechAdapt) showed how a mid-sized SaaS firm’s growth stalled due to poor alignment of its sales, marketing, and product goals, illustrating the need for go-to-market governance as companies expand. The root cause is often fast growth without sufficient emphasis on communication structures and a unified strategy.
Scaling the Sales Engine – Moving from founder-led sales to a scalable sales organisation is a notorious scale-up challenge. Early GTM success can create bottlenecks as demand outpaces the startup’s ad-hoc processes. Many scale-ups prematurely scale sales before fully validating their product-market fit or repeatable sales model – “leaning too heavily on the promise of product-led growth” and assuming the ideal customer profile is nailed down from the start. This often leads to overextended teams “tripping over themselves” with inconsistent sales execution.
Common issues include breakdowns in sales process, lack of specialisation, and hiring too quickly or into the wrong roles. For instance, without defined sales roles, reps may juggle prospecting and closing in a stop-start fashion, hindering steady pipeline flow.
On the enterprise side, the challenge is optimising a large sales force, ensuring salespeople are enabled with the right training and resources to sell complex products. Unrealistic sales quotas at big companies can incentivise bad behaviour and short-termism while too many overlay roles or bureaucracy can bog down the sales cycle.
Both, scale-ups, and enterprises, must continuously fine-tune their sales strategy (territories, roles, playbooks) to maintain GTM effectiveness as they grow.
Marketing at Scale & Brand Consistency – Scaling marketing from a scrappy startup approach to a structured, multi-channel engine is another growth pain point. Scale-ups often struggle to build broad awareness on limited budgets and may rely on a few channels that eventually plateau. Enterprises have large marketing teams and budgets, but ensuring consistent messaging across regions or product lines is difficult.
A strong brand and thought leadership presence becomes critical as companies mature – in crowded markets, brand differentiation and reputation “create a halo that attracts customers, even before direct outreach”. Achieving this requires aligning product marketing, content, and demand generation around a cohesive story.
Challenges include coordinating campaigns across global teams, avoiding redundant or conflicting outreach, and adapting to new marketing trends (e.g. video, community-building, influencer marketing). If marketing and sales are not tightly aligned on target segments and messaging, generated leads may not convert effectively, wasting effort.
Cross-functional planning (e.g. joint sales-marketing quarterly plans) and shared metrics are practices used to tackle this, but implementing them amid rapid growth is an ongoing struggle.
Data Silos and Tools Integration – As GTM operations expand, companies grapple with managing data and analytics across many tools (CRM, marketing automation, customer databases). In a small startup, keeping track of leads and customers might be straightforward, but at scale, the lack of a “single source of truth” can hurt decision-making.
A warning sign in scaling GTM is when sales activity data is scattered in disparate places with no central visibility. Without reliable, unified data, teams lose transparency and trust in metrics. Scale-ups often reach a point where implementing a robust CRM and analytics framework is imperative to continue growing.
Enterprises might have these systems, but they face their own challenges: legacy tools that don’t talk to each other, or mountains of data that aren’t effectively analysed. Data-driven decision-making is crucial – intuition must give way to insight from metrics.
A lack of it can cause companies to miss signs of GTM problems (e.g. a spike in churn or drop in lead quality). However, instituting a data-driven culture and integrating systems is a non-trivial challenge, often requiring investment in revenue operations roles and data infrastructure.
Maintaining Agility and GTM Fit – Both fast-growing and large organizations can fall prey to a rigid strategy that no longer fits the market. The SaaS landscape evolves quickly (new competitors, buyer preferences, technologies), so GTM approaches must adapt in kind. Scale-ups sometimes cling to an initial strategy that worked at $1M ARR but falters at $10M+ as the customer base broadens. Enterprises might rely on playbooks that are years old.
Winning new customers is only half of a successful SaaS GTM – retaining and growing those customers is equally vital, especially amid economic pressures. Scale-ups and enterprises alike face challenges in building robust customer success motions:
Onboarding and Implementation Friction – A clunky onboarding experience for new customers can sour the relationship from the start. Scale-ups may struggle here due to limited customer success staff or immature onboarding processes, resulting in low adoption and early churn.
Enterprise software providers, on the other hand, often manage large-scale implementations that are complex – if not handled smoothly (with proper training, integration support, etc.), customers may never fully realise the product’s value.
The GTM challenge is to ensure customers quickly reach their “aha moment.” Companies that neglect onboarding or assume customers will figure things out risk a bad first impression and ultimately, public churn stories that harm their reputation.
Many organisations are investing in more structured customer onboarding programs (checklists, customer education, dedicated onboarding teams) to combat this challenge.
Churn and Maximising Lifetime Value – Customer churn directly undermines growth; high churn means a leaky bucket where new sales barely replace lost clients. Scale-ups often initially focus on acquisition and treat customer success as an afterthought “until the churn rate swells”. This reactive approach can stall growth when expansion revenue and renewals fail to materialise.
Enterprises typically have established customer success and account management teams to drive renewals and upsells, but they can face churn in specific segments or due to competition offering better value. Both must balance growth with profitability by extending customer lifetime value (LTV). Investors and boards in 2025 are pushing companies to pay more attention to net retention.
One major challenge is building programs that proactively drive adoption and showcase ROI to customers. If support is “inadequate or not timely, it leads to frustration and churn”. Moreover, companies must identify at-risk accounts early (using health scores, usage data) and intervene, which circles back to the data challenge. The root cause of churn often lies in poor alignment of product promise and customer reality, or in neglecting the relationship post-sale.
Scaling Customer Success Teams – As the customer base grows, scaling the customer success function becomes critical and tricky. A scale-up landing its first 50 customers may manage with a small team, but to support hundreds or thousands of customers (especially enterprise clients with complex needs), it must invest in CS headcount, training, and possibly tiered support models.
Hiring and funding CS at the right pace is a known challenge – too few CSMs (Customer Success Managers) and each client gets little attention; too many too soon and it strains finances. Enterprises with thousands of clients often tier their customer success approach (high-touch for big accounts, tech-touch for long-tail), but ensuring quality across the board is hard.
Additionally, aligning Sales and Customer Success is crucial: sales teams might promise features or timelines to win deals that CS then has to deliver on, and a lack of post-sales alignment can create customer dissatisfaction.
Organisations are increasingly viewing customer success as a revenue driver rather than a cost center, since upsells and renewals can contribute heavily to growth. The challenge is cultural as well – getting all GTM functions to value retention.
Metrics like net revenue retention (NRR), gross churn rate, and customer satisfaction (CSAT) become key GTM indicators to monitor. In sum, turning customers into long-term advocates requires overcoming internal silos and treating customer success with the same urgency as new sales.
Expansion and Cross-Sell Complexity – Mature SaaS enterprises often have multiple products or modules, and part of their GTM strategy is “land and expand” – i.e., sell more to existing accounts. While this is a growth opportunity, it presents challenges in practice. Sales and CS teams must coordinate on identifying expansion opportunities without coming off as just pushing more product.
Enterprises can struggle with internal coordination on account planning (e.g., who owns the upsell number – the account executive or the customer success manager?). Meanwhile, scale-ups that introduce new product offerings face the GTM challenge of educating existing customers on additional value. If the value messaging for new modules isn’t clear, these cross-sell efforts can falter.
McKinsey research noted that adding product lines is a proven growth booster for scaling companies, but it requires refined messaging and sometimes a “startup within a startup” approach with dedicated marketing campaigns.
The root issue is ensuring the organization can sell across a broader solution set without losing focus or confusing customers. Done right, strong customer success can actually facilitate expansion by regularly demonstrating value and uncovering pain points that additional products can solve.
A company’s product offering and how it fits customer needs lie at the heart of GTM. Both scale-ups and enterprises face challenges in aligning product strategy with go-to-market execution:
Maintaining Product-Market Fit at Scale – Achieving product-market fit is the first milestone for a startup, but maintaining it is an ongoing challenge as the market evolves. Some scale-ups hit initial fit in a niche but struggle to adjust the product for broader appeal or new verticals. GTM teams may find that what resonated with early adopters doesn’t work for more mainstream customers.
It’s a serious pitfall to ignore product-market fit signals – building features no one asked for or selling to the wrong customer segment is “a recipe for disaster”. Enterprises can also drift away from market needs, especially if they become complacent or rely on a legacy cash-cow product while competitors innovate. Regularly collecting customer feedback and updating the roadmap is critical.
A cross-functional challenge is ensuring sales and customer success relay market feedback to product management, and that product adjusts in response. Companies that fail to adapt (e.g. missing the shift to AI or new integration standards) find their GTM efforts increasingly uphill. Agile competitors can catch incumbents off-guard, so continuous market sensing and product iteration are part of GTM strategy now.
For instance, Slack gained rapid adoption with a new take on workplace communication; in response, Microsoft had to quickly evolve Teams as a competing product – a scenario demonstrating how product fit and GTM must evolve together in competitive cycles.
Pricing and Packaging Complexity – Crafting the right pricing model is a perennial GTM challenge that intensifies with growth. Scale-ups often experiment with pricing tiers, freemiums, or usage-based models to find what maximises conversion and revenue.
It’s easy to get it wrong – a price too high can alienate cost-sensitive prospects, while underpricing can devalue the product or hurt margins. As companies expand to new markets (UK vs US, SMB vs enterprise), they frequently need flexible pricing options (monthly vs annual, volume discounts, etc.).
Enterprises with multiple products face the challenge of bundling or cross-product pricing, ensuring simplicity for customers yet fair value capture. Internally, pricing changes can create friction between Product (owning packaging) and Sales (who need pricing that helps close deals).
A related challenge is discounting discipline – high-growth companies might over-discount to win deals, harming long-term economics. In 2025, with heightened profitability pressures, both scale-ups and big vendors are rethinking pricing strategies (for example, many SaaS firms are introducing usage-based components or limiting deep discounts).
The key is aligning pricing with the value delivered and the expectations of the target segment. A misstep on pricing strategy can directly undermine GTM success, so many organisations are establishing dedicated pricing teams or processes as they mature.
User Experience (UX) and Free Trial Conversions – In product-led GTM motions especially, the product experience itself is a major driver of sales. A weak free trial or demo that fails to showcase the product’s value is a lost GTM opportunity. Scale-up SaaS companies often rely on free trials or freemium models to generate bottom-up adoption, but if the onboarding UX is confusing or the value isn’t apparent quickly, prospects drop off and don’t convert. This is a cross-functional issue: product design must work hand-in-hand with marketing (to set correct expectations) and customer success (to nurture trial users).
Enterprises may rely less on free trials for sales, but user experience is still crucial for adoption and renewal. Large B2B platforms that are clunky and unintuitive face user resistance, hurting engagement and upsell opportunities. One noted challenge is that some enterprise software companies underestimated the importance of UX, leading to frustrated users and slower product adoption.
In today’s market, business users expect a consumer-grade experience. Companies are addressing this by investing in UX design and even product-led growth (PLG) strategies, where product usage data informs the GTM approach. The alignment of product and GTM is evident here: a great product experience can significantly lower sales friction, whereas a poor one increases the load on salespeople to convince customers.
Security and Compliance as GTM Barriers – Particularly for cloud tech and SaaS dealing with enterprise clients, security requirements and compliance considerations have become a front-and-center GTM factor. High-profile data breaches have made customers extremely cautious.
Scale-up companies often find that to sell into large accounts (in finance, healthcare, public sector, etc.), they must meet stringent security certifications (SOC 2, ISO 27001) and compliance standards. This can be challenging due to the cost and expertise needed. Yet, it’s not optional – a robust security posture is “no longer an option; it's a necessity” for earning customer trust.
Enterprises presumably have mature security, but even they face GTM hurdles if a new product lacks a proven security track record or if a competitor touts superior privacy features. Additionally, differing regulations (like data residency laws in the UK/EU vs. US) mean GTM messaging and operations must adapt (e.g., offering EU-based data hosting to satisfy European clients).
Marketing teams now often collaborate with security and legal departments to highlight data protection measures as part of the sales pitch. Trust signals (certifications, compliance badges, transparent policies) have become important marketing assets.
The challenge is that security is a moving target – threats evolve, laws change, and GTM teams must keep up. Organisations that handle this well make security/privacy a selling point rather than a hurdle, turning what could be a challenge into a competitive advantage in the market.
While scale-ups and enterprise-level SaaS companies face many of the same GTM themes, the context of company size and maturity causes these challenges to manifest differently. The table below compares how key GTM challenge areas typically differ between high-growth scale-ups and established enterprises:
| Challenge Area | Scale-Up Perspective | Enterprise Perspective |
|---|---|---|
| Market Position & Competition |
Struggle to gain credibility and awareness against larger, well-known competitors. Must differentiate sharply to break into the market. Often niche-focused to avoid going head-to-head with giants. (Example: a UK HR-tech scale-up might focus on one innovative feature to stand out among big HR platforms.) |
Concerned with defending market share from upstart disruptors and other incumbents. Need to avoid complacency – must continue to innovate GTM to maintain leadership. Competition is global, and brand is an asset, but also a big target. |
| Resource Constraints vs. Complexity |
Limited resources and headcount force prioritisation. GTM teams wear multiple hats (one person might handle marketing ops, sales enablement, and analytics). Funding constraints can limit how fast they scale sales and marketing – if they grow too fast without enough runway, GTM efforts stall. The challenge is doing more with less and securing the right funding for sustainable growth. |
Ample resources but high complexity. Large budgets and teams can lead to waste or inefficiency if not coordinated. Multiple product lines, regions, and large hierarchies introduce bureaucracy and silos, which can slow GTM execution. The challenge is doing more with the coordination of many moving parts (ensuring one division’s actions don’t conflict with another) and maintaining efficiency at scale. |
| Sales Process & Cycles |
Building a repeatable sales process from scratch. Likely dealing with shorter sales cycles at first (selling to mid-market) but aspiring to move upmarket, introducing longer, more complex deals that they have less experience with. Key challenges include hiring first sales leaders, creating playbooks, and establishing forecasting discipline. They may also rely on founders for sales in early stages, when transitioning to a team-based approach is a hurdle. |
Optimising an established sales force and processes. Often they deal with long enterprise sales cycles and procurement hurdles by default. The challenge lies in keeping the sales org agile (avoiding rigid old-school methods), ensuring sales enablement for large product catalogs, and coordinating global account management while managing channel/partner sales in addition to direct. Ensuring sales teams hit ambitious targets without burning out or resorting to bad deals (e.g. deep discounts) is an ongoing concern. |
| Marketing & GTM Strategy |
Low brand recognition means marketing’s priority is building awareness and generating demand quickly. Likely focus on cost-effective digital channels, content marketing, and maybe product-led growth due to smaller budgets. GTM strategy might pivot often as they experiment to find what sticks. They need to zero in on an ICP and messaging that resonates, and avoid chasing every opportunity. One misstep (like messaging the wrong audience) can waste precious resources. |
Well known brand can open doors, but marketing faces the challenge of keeping the brand relevant and differentiated as markets evolve. Larger marketing teams run multi-channel campaigns (events, ABM, PR, etc.) where coordination is critical. There’s also an emphasis on thought leadership to maintain authority in the industry. Strategy is more set, with playbooks for segments, but the risk of strategy inertia, a reluctance to change tactics that worked in the past even if the market is shifting. Enterprise marketers also must personalise at scale (account-based marketing to hundreds of key accounts), which is challenging. |
| Customer Success & Retention |
Often under-invested early on the company is primarily focused on acquiring customers and proving the business. As a result, churn can creep up. Scale-ups may not have formal customer success until growth stalls due to churn. The team is typically reactive (putting out fires for big clients) rather than proactive. However, those who recognise retention's importance early and build CS programs gain an edge in lifetime value. Increasing NRR to 115% and beyond. |
Dedicated customer success and support departments with defined processes (onboarding, QBRs, support SLAs). The challenge is maintaining a high-quality, personalised touch as the customer base scales. Enterprises can become metrics-driven to the point of treating customers as numbers risking customer satisfaction. They must manage a wide range of customers: from small clients (who might get automated touch) to large strategic accounts (which expect white-glove service). Ensuring renewals across this spectrum is complex. Also, aligning sales promises with delivery is a major focus to prevent churn. |
| Organisational Alignment |
Founders and early leaders directly drive alignment (which can be easier in a small team), but as the team grows from, say, 20 to 200, misalignment grows quickly if not checked. New layers of management and new teams (sales, marketing, product, CS) might lack clear roles initially, which can cause confusion. The company is establishing its culture and communication cadence, so there’s vulnerability to silo formation in this formative stage. |
More formal structures (business units, regional teams) which can create silos by default. Aligning everyone to the same vision is an ongoing effort – large enterprises often implement OKRs or regular all-hands meetings to keep alignment, but division-level KPIs can sometimes conflict. The C-suite needs to actively break down silos (e.g., ensure Marketing, Sales, Product leaders collaborate regularly). Organisational agility is harder to maintain, so leadership has to deliberately encourage cross-functional projects and knowledge sharing to avoid teams operating on “islands.” |
Key Takeaway: Scale-ups and enterprises ultimately grapple with similar GTM pain points – understanding the customer and market, executing efficiently, and retaining customers – but the scale and context change the nature of the challenge.
Scale-ups deal with finding a repeatable model and fighting for recognition, whereas enterprises focus on refining and evolving their model while managing complexity. Importantly, both must emphasise cross-functional alignment and customer-centricity to succeed.
GTM challenges in B2B SaaS are multifaceted, intensifying with growth and competition. Scale-up companies in the UK and USA often confront issues like establishing their market niche, scaling sales processes, and avoiding silos as they expand. Enterprise-level firms face the complexity of large organisations – ensuring different departments work in concert, keeping their offerings and messaging fresh, and sustaining growth in saturated markets.
Common themes emerge across both: the need for crystal-clear positioning in a crowded arena, alignment of sales and marketing efforts (and indeed all customer-facing functions), diligent focus on customer success to drive retention, and continuous strategy adaptation as conditions change.
The root causes of GTM challenges often boil down to companies stretching beyond their initial comfort zone – whether its a startup growing too fast without process, or a big company struggling to stay agile.
In all cases, a customer-centric, data-driven, and collaborative approach to go-to-market is the antidote. By recognising these recurring challenges and learning from others’ experiences (as seen in the examples and cases above), SaaS and cloud companies can anticipate pitfalls and craft strategies to overcome them, turning GTM execution into a competitive advantage rather than a bottleneck.
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