Growing a company is never a one-step process. Moving from $1 million to $5 million, $5 million to $10 million, and beyond $10 million, or even $20 million to $50 million, each requires new skills, new structures, and new ways of thinking. What worked in the early days of personal networks and ad hoc processes won’t scale once you’re juggling a larger pipeline, a bigger team, and more complex market demands.

Executives who excelled at one stage can find themselves out of their depth when confronted with the next.

Scaling from $1 million to $5 million, $5 million to $10 million, and beyond isn’t just a matter of bigger numbers, leadership needs to evolve. Each phase demands new skills, processes, and mindsets. Even executives who excelled early on can find themselves at a loss if they’re not adapting in lockstep with the company’s growth.

Executive Team Growth

Below are examples of a few common practices that work at lower-revenue stages but must evolve as companies grow through multiple revenue tiers. You’ll see how a practice that works well in an early stage can suddenly become a liability as your organization expands. I also highlight continuous improvement metrics examples that help executives focus on where and how they need to grow.

1. VP of Sales

Example: Heavy Reliance on Personal Networks

Early-Stage Success ($1M–$5M):

When your startup is small, the VP of Sales (and often the founder) can close deals through personal contacts. Handshakes, warm introductions, and a solid reputation can quickly net the first million in revenue.

Why It Fails as You Scale (Beyond $5M–$10M+):

Reliance on personal Rolodexes can’t sustain bigger revenue targets. At higher volumes, you need a repeatable sales engine built on consistent prospecting, lead qualification, and CRM-driven pipelines.

Continuous Improvement Metric:

Non-Network Leads: Track what percentage of closed deals originate from scalable channels (inbound marketing, outbound sales campaigns) versus personal connections. This keeps the VP of Sales focused on systematically growing deal flow—rather than relying on who they already know.

2. VP of Marketing

Example: One-Person Show for Campaigns

Early-Stage Success ($1M–$5M):

With limited resources, a VP of Marketing might handle everything—email campaigns, social media, events—often with minimal budget or staff. A nimble, hands-on style works well when the marketing footprint is small.

Why It Fails as You Scale (Beyond $5M–$10M+):

As the company grows, marketing becomes more complex. You need specialized skills (SEO, paid media, product marketing, analytics) and coordinated campaigns that target multiple segments. A lone marketer, no matter how talented, will struggle to drive sustained brand awareness and lead generation at scale.

Continuous Improvement Metric:

Channel Performance & ROI: Instead of just looking at total leads or brand impressions, measure ROI per channel (e.g., cost per lead, conversion rate by campaign). This ensures the VP of Marketing is building a data-driven strategy and delegating specialized tasks to the right team members or agencies.

3. VP of Engineering (CTO or Head of Dev)

Example: Heroic Firefighting of Production Issues

Early-Stage Success ($1M–$5M):

When the product is small and user volume is manageable, the VP of Engineering can personally jump in to fix bugs, deploy code, and handle emergencies. This rapid response can feel impressive and efficient in a tight-knit dev team.

Why It Fails as You Scale (Beyond $5M–$10M+):

As user bases multiply and features expand, firefighting doesn’t cut it. You need robust development processes—version control best practices, automated testing, continuous integration, and dedicated teams for QA or site reliability. Otherwise, technical debt and outages will spiral out of control.

Continuous Improvement Metric:

Deployment Frequency & Error Rates: Track how often releases happen (weekly, daily, hourly) and the number of critical bugs per release. The goal is to continuously refine release pipelines and reduce production hiccups—shifting from heroism to systematized reliability.

4. CFO or VP of Finance

Example: Managing Cash Flow on Spreadsheets

Early-Stage Success ($1M–$5M):

Early on, managing finances with basic spreadsheets or simple accounting software can work just fine—accounts receivable, cash flow, and vendor payments are all visible to a small finance team.

Why It Fails as You Scale (Beyond $5M–$10M+):

More revenue means more complexity—multiple revenue streams, higher headcount, and often global expansions. Spreadsheets become error-prone and don’t provide real-time insights. You’ll need advanced financial systems, robust forecasting models, and possibly compliance with greater regulatory requirements.

Continuous Improvement Metric:

Forecast Accuracy & Time to Close Books: Compare predicted cash flow to actual, and measure how quickly monthly or quarterly books are finalized. A CFO who is continuously refining these metrics is ensuring scalable financial operations and better strategic planning.

5. COO or VP of Operations

Example: Doing Everything Ad Hoc

Early-Stage Success ($1M–$5M):

In smaller startups, the COO might personally coordinate vendor relationships, shipping processes, customer success efforts, and HR tasks. This ad-hoc, reactive approach can be quite effective when volume is low.

Why It Fails as You Scale (Beyond $5M–$10M+):

Once a company crosses multiple growth thresholds, complexities balloon. Operations need repeatable processes and systems—whether it’s inventory management, logistics, or inter-departmental coordination. A purely reactive COO gets overwhelmed, bottlenecking growth.

Continuous Improvement Metric:

Process Efficiency & Automation Rates: Track how many operational tasks become standardized or automated every quarter (e.g., implementing an inventory management system, automating order tracking). This metric drives the COO to focus on scalable solutions, not just daily firefighting.

Putting It All Together: Evolving Through Continuous Improvement

At each stage of growth, whether you’re going from $1 million to $5 million, $5 million to $10 million, or $10 million to $50 million, what got you here won’t get you there. A VP of Sales who excels at personal-network selling might stall without a broader pipeline strategy. A one-person-show marketer will struggle to manage extensive multi-channel campaigns. The same story holds true for engineering, finance, and operations.

That’s where continuous improvement metrics come in. By emphasizing forward-looking, process-centric KPIs, instead of just relying on revenue or profit, CEOs can:

Identify Skill Gaps: When each leader is measured on a relevant continuous improvement metric, weaknesses become clear faster.

Guide Executive Evolution: With tangible KPIs, executives know exactly what to improve next, be it sales processes, marketing ROI, engineering reliability, financial forecasting, or operational efficiency.

Prevent Complacency: Past successes can breed overconfidence. Regularly updated continuous improvement targets keep leaders in a growth mindset, ready for the next challenge.

Final Thoughts

Every growth milestone adds new layers of complexity. If you’re relying on the same tactics that worked in a smaller, scrappier environment, you’ll quickly hit a plateau. As the CEO, your job is to help each executive level up, and continuous improvement metrics are the blueprint for that evolution.

Executives who don’t adapt risk being left behind. Hands-on heroics and gut-driven methods might work at one stage, but structured processes, proactive engagement, specialized teams, and data-driven decisions take center stage at the next.

For CEOs and boards, don’t just rely on lagging financial indicators to measure executives’ performance. If you want them to keep evolving, you must guide them with continuous improvement metrics that make it clear what needs to change at each new phase of growth. By doing so, you’ll foster a leadership team that consistently refines their approach—turning short-term successes into long-term, scalable victories.