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In healthcare, growth rarely fails for lack of ambition. It more often fails due to not having the right talent at the right time. One of the most critical post-investment decisions is determining when to hire a Chief Revenue Officer (CRO), and what kind of leader the business truly needs.
As revenue scales, the CRO’s role evolves dramatically. What works at $25M ARR rarely works at $100M. Not because someone “outgrows” the role, but because the problems to solve change.
Each ARR inflection point represents a new level of go-to-market sophistication, buyer complexity, and organizational design. Understanding what to solve for at each stage helps founders, boards, and investors align leadership capability with company maturity. The following sections outline how those variables shift as revenue grows and how CRO leadership can accelerate results.
Insights contributed by healthcare executives Rick Dean, Terry Boch, and Omar Nagji.
Goal:
The objective in this earliest stage is to establish product-market fit and secure early customers who will shape the roadmap. The organization is working to understand who finds the product valuable, why, and under what conditions.
Ideal Leader:
The ideal commercial leader is a builder rather than a polished operator—someone who is still selling directly, learning quickly, and adapting even faster. This leader earns trust not by relying on a perfected script but by demonstrating genuine curiosity about the customer’s world and translating raw feedback into early messaging.
You’re Solving For:
The company is attempting to align product capabilities with true customer needs while putting in place just enough structure to learn systematically. This includes implementing a basic CRM instance, establishing early pricing, defining the initial ICP, and creating simple contracting standards. This is also where the discipline emerges to say no to revenue that does not align with the long-term strategy.
Goal:
The focus shifts to transforming a founder-driven motion into something teachable and repeatable that does not rely on intuition or individual heroics.
Ideal Leader:
A CRO at this stage must still be capable of carrying a bag, but they also bring the structure required to formalize the motion. They define qualification criteria, introduce early forecasting habits, refine buyer personas, and put guardrails around pricing and contracting.
You’re Solving For:
The company is solving for institutional clarity—understanding why deals close, how they progress, and where they stall. Funnel math starts to matter, ICP definitions sharpen, and onboarding becomes more consistent. The organization begins to shift from instinct to intention.
Goal:
At this point, the goal is to build a revenue engine that scales because the system works—not because a handful of exceptional individuals carry the load.
Ideal Leader:
The right CRO is a true player-coach transitioning into a strategic operator. They design compensation plans that reinforce the right behaviors, create training and enablement that allow B-players to succeed, and formalize Revenue Operations to bring discipline to forecasting and performance management.
You’re Solving For:
The company is solving for predictable rep productivity, reliable forecast accuracy, and the early indicators necessary to prove scalability. Churn and Net Revenue Retention become critical measures, and addressing them becomes foundational before adding more headcount.
Goal:
The organization must ensure that the commercial motion is not just working in pockets but is consistently executed across the entire team.
Ideal Leader:
The CRO best suited for this stage has taken a business from roughly $10M to $50M ARR and understands how to turn early-stage scrappiness into durable, repeatable systems. They bring the judgment needed to scale hiring, onboarding, segmentation, and messaging.
You’re Solving For:
The business is solving for stronger segmentation, more accurate forecasting, and a demand engine that ties Marketing and Sales into a cohesive GTM motion. Repeatability becomes the defining characteristic separating businesses that scale smoothly from those that plateau.
Goal:
The goal in this stage is to introduce operational rigor and deeper specialization as complexity increases across markets, products, and buyer types.
Ideal Leader:
The ideal CRO has experience managing scale from approximately $25M to $100M ARR and understands how to lead across payer, provider, employer, and life sciences segments. They bring a more sophisticated operating cadence, deeper analytical discipline, and the ability to manage multiple revenue motions simultaneously.
You’re Solving For:
The organization is addressing more exacting unit economics, greater data-driven management, and improved alignment between product and revenue strategy. Marketing-sourced pipeline becomes a more important component of growth, and capacity planning becomes a board-level conversation.
Goal:
The company must now optimize for efficiency rather than growth through headcount. The emphasis shifts to aligning Sales, Marketing, Customer Success, and Product through shared metrics, shared systems, and coordinated planning.
Ideal Leader:
The CRO suited for this stage is a strategic orchestrator—someone who integrates the entire commercial ecosystem. They are skilled at managing multi-year enterprise contracts, coordinating multi-product GTM strategy, and navigating cross-functional complexity with precision.
You’re Solving For:
The organization is solving for true cross-functional orchestration and productivity gains that come from process quality rather than additional headcount. Predictability becomes central, enabling Finance, Product, and Operations to make confident planning decisions. At this stage, the CRO begins operating with the mindset of a COO or CEO.
Goal:
Beyond $100M ARR, the company’s focus shifts to preparing for IPO, M&A, or strategic exit while institutionalizing operating discipline and profit-focused growth.
Ideal Leader:
The CRO capable of leading at this scale brings global enterprise experience, financial fluency, governance capabilities, and often M&A integration expertise. They understand how to architect a multi-product revenue strategy while managing risk-based payer and provider relationships.
You’re Solving For:
The company is solving for operating leverage, valuation expansion, strategic channel partnerships, and tight alignment between revenue execution and corporate strategy. At this level, the CRO is no longer simply driving revenue—they are shaping the long-term strategic identity of the business.
The most successful healthcare scale stories happen when capital and capability grow in sync. When both sides recognize that the right CRO at the right time can be the difference between momentum and stall speed, the entire trajectory of the business changes.
The right CRO is not simply a seller. They are an intellectually curious business leader who earns trust through understanding, not persuasion. As healthcare executive Rick Dean puts it: “Finding a trusted CRO who’s been a successful individual contributor and who brings genuine intellectual curiosity is critical. Selling today isn’t about dialing for leads—it’s about understanding the customer’s business and starting a trusted relationship long before a deal.”
“Finding a trusted CRO who’s been a successful individual contributor and who brings genuine intellectual curiosity is critical. Selling today isn’t about dialing for leads—it’s about understanding the customer’s business and starting a trusted relationship long before a deal.”
RICK DEAN, FORMER CEO, ONCO HEALTH
This article was written by David Woodward, Partner at Chasm Partners. To continue the conversation with David, connect with him on LinkedIn or email him at [email protected].