Why Is Selling in Healthcare So Hard?

Selling in healthcare especially for digital health startups and healthcare services companies targeting employers is notoriously difficult. Unlike traditional sales, it’s not just about having a great product; it’s about navigating a highly complex B2B sales environment with multiple decision-makers, competing priorities, and lengthy sales cycles.

To succeed, sales professionals must understand the interaction of two key B2B sales dynamics:

1) The Shifting Importance of Fit, Risk, and Price

In the book Hope Is Not a Strategy, the sales process is broken down into three core concerns:

Fit – Does the solution meet the employer’s needs?

Risk – Will adopting this solution cause disruption or unintended consequences?

Price – Is it cost-effective compared to alternatives?

Throughout the sales cycle, these priorities shift. Early on, buyers focus on Fit—does this solution solve their problem? Later, Risk becomes the dominant concern—will it integrate smoothly? Finally, Price becomes the deciding factor.

2) The Multi-Stakeholder Buying Team

The Miller Heiman Strategy highlights that large B2B purchases involve multiple stakeholders, each with different decision-making criteria:

Technical Buyers – Focus on operational feasibility and integration.

Outcome Buyers – Care about clinical or business impact.

Financial Buyers – Prioritize cost-effectiveness and ROI.

The Sales Challenge: A 3x3 Matrix of Priorities

If we map these two frameworks together, we get a 3x3 matrix where every buyer type (Technical, Outcome, Financial) evaluates the product through the lens of Fit, Risk, and Price but at different times and with different priorities.

The Hardest Part: Managing Conflicting Priorities in Real-Time

In every sales meeting, different buyers are in different stages of the Fit, Risk, Price evaluation—simultaneously. One person might be worried about implementation challenges (Risk) while another is focused on long-term value (Fit) and yet another is pushing back on cost (Price).

To succeed, sales professionals must:

Identify each buyer type early – Who in the room is a Technical, Outcome, or Financial Buyer?

Gauge their priorities – Are they focused on Fit, Risk, or Price at this moment?

Address all concerns simultaneously – Speak to the right priorities for each stakeholder without losing control of the conversation.

Hard? Yes. Doable? Absolutely.

Winning healthcare B2B sales requires a structured approach, deep stakeholder understanding, and the ability to manage multiple narratives at once. By mastering the Fit, Risk, Price model and recognizing the distinct needs of Technical, Outcome, and Financial buyers, sales teams can navigate complexity and close deals with confidence.

What’s been your biggest challenge in healthcare sales? Drop a comment below!

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