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The $20-50M range represents a unique transition point—you're too big for the all-hands-on-deck, founder-driven execution that powered early growth, but not yet large enough to afford the robust operational infrastructure of enterprise organizations. This creates an execution limbo where companies must navigate complex challenges with incomplete systems.
Based on our work with dozens of companies in this range, we've identified four specific execution gaps that consistently derail growth. Companies that proactively address these gaps accelerate through this phase; those that don't often plateau or regress.
At $20-50M, companies typically have a clear strategic vision at the leadership level. The problem isn't strategy formation—it's strategy translation.
The gap in action: Leaders articulate a compelling vision and strategic priorities, but these fail to shape day-to-day decisions across the organization. Middle managers interpret strategic direction differently, and frontline execution becomes inconsistent with leadership intent.
The fix—Strategic Translation Infrastructure:
A SaaS platform company exemplified this approach after experiencing growth stalls at $28M. Despite a clear account expansion strategy at the leadership level, customer-facing teams continued prioritizing new logos over expansion opportunities. By implementing function-specific strategy decode sessions and creating role-specific "strategic impact maps," they realigned frontline activities with strategic priorities. The result: expansion revenue grew from 32% to 52% of new ARR within two quarters.
As organizations grow beyond $20M, departmental optimization often comes at the expense of cross-functional integration. Functions become increasingly specialized and develop their own priorities, processes, and perspectives.
The gap in action: Handoffs between departments break down, cross-functional initiatives stall, and customer experiences become fragmented as information and accountability get lost between organizational silos.
The fix—Coordination Architecture:
A marketing technology company struggled with this gap as they approached $35M. Customer implementations required coordination across sales, product, engineering, and customer success, but delays and quality issues plagued the process. By implementing a dedicated customer onboarding function with end-to-end process ownership and shared success metrics across departments, they reduced implementation time by 48% and improved customer satisfaction scores from 6.4 to 8.2.
Companies scaling through $20-50M often fly blind—lacking the instrumentation to see how their operations are actually performing until problems manifest in financial results.
The gap in action: Leaders discover execution problems only after they've already impacted results. Root causes remain obscure, making it difficult to implement effective solutions. The organization reacts to symptoms rather than addressing underlying issues.
The fix—Operational Instrumentation:
A B2B software company at $42M struggled with unpredictable sales performance that seemed to defy explanation. By implementing an operational dashboard that tracked leading indicators like demo-to-proposal ratios, proposal quality scores, and deal velocity metrics, they identified specific breakdowns in their sales process. This visibility allowed targeted interventions that increased close rates by 22% within one quarter.
As companies scale beyond $20M, the capabilities that drove initial success become insufficient for new challenges. Yet many organizations continue hiring for today's needs rather than building the capabilities required for tomorrow's complexity.
The gap in action: Teams struggle to execute increasingly sophisticated strategies. New initiatives falter not from lack of effort but from lack of capability. The organization develops workarounds rather than closing skill gaps.
The fix—Systematic Capability Development:
A FinTech company at $26M recognized they lacked the enterprise sales capabilities needed to target larger financial institutions. Rather than just hiring external talent, they implemented a structured capability development program that included role shadowing, progressive skill certification, and a dedicated "enterprise sales university." Within six months, average deal size increased by 3.6x, and they closed their first $1M+ annual contract.
What unites these fixes is a fundamental shift from ad-hoc execution to systematic execution architecture. Companies that break through the $50M barrier don't just address individual gaps—they build integrated execution systems that connect strategic intent to operational reality.
The components of an effective execution system include:
An eCommerce platform company at $32M illustrates this systemic approach to closing execution gaps. After three quarters of stalled growth, they worked with embedded operators to implement an integrated execution system that addressed all four gaps:
Within six months, they accelerated growth to 9% quarter-over-quarter (up from 3%) while actually reducing their burn rate through improved operational efficiency.
The key insight: Execution excellence at the $20-50M stage isn't about working harder—it's about building the systems that convert strategy into consistent results. By identifying and addressing these four execution gaps, you can transform the operational foundation of your business from a growth constraint into a strategic advantage.
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Execution vs. Strategy Problems
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Essential Systems for Scaling.webp)
Embedded Operators vs. Consultants
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