Ten Pipeline Optimization Challenges and Ideas

One of the nagging challenges in B2B marketing is pipeline optimization. Over the last month, we have had in-depth discussions with 40+ healthcare technology marketing leaders about how to accelerate and optimize the marketing pipeline so that more deals convert faster.

In addition, my colleague Mark Erwich interviewed two longtime healthcare marketing leaders, Michael Passanante and Amy Swanson. All three executives have deep experience in this area. In the latest episode of the Healthtech Marketing Show, Michael, Amy, and Mark discuss the typical challenges they have faced and how they have developed effective ways to optimize pipelines.

Listen to Mark, Michael, and Amy

Let’s review the ten most common issues with an idea on how to solve these.

1. Pipeline Ownership & Alignment

The age-old issue is that when sales, marketing, and customer success departments are siloed, it is much harder to share common goals. This inevitably creates disconnected pipeline efforts.

Solution – Collaborative Scorecards and a Pipeline Council

Get a better handle on pipeline optimization by implementing collaborative scorecards with shared KPIs across marketing, sales, and customer success to create joint accountability for the total pipeline.

You can download an example here.

• Create a monthly “Pipeline Council” meeting with leaders from marketing, sales, and customer success.
• Develop a single-page dashboard showing agreed-upon metrics like total pipeline generated, conversion rates by stage, and marketing influence percentage.
• Have each department commit to specific actions that contribute to shared goals rather than departmental metrics. Celebrate wins collectively and problem-solve bottlenecks together.

2. Marketing Attribution Through Long Sales Cycles

Healthcare’s lengthy sales cycles (often 9-18+ months) make tracking marketing influence difficult. How do you attribute the value of marketing when deals are longer than a year in many cases?

Solution – Extended attribution lookback periods and connect attribution from early marketing engagement to eventual opportunities

• Configure your CRM to maintain an 18-month attribution window for healthcare accounts.
• Create a “First Touch Timeline” report that visually maps the first marketing touchpoint with each closed deal, even if it occurred over a year before opportunity creation.
• Track additional touches over the course of the deal progression.
• Share this report quarterly with leadership to demonstrate marketing’s early influence.
• Use this data to inform content creation 12+ months before expected buying windows.

3. Identifying & Engaging Complete Buying Committees

Healthcare decisions involve numerous stakeholders, many of whom never appear in opportunity records. How do you progressively engage multiple members of the buying committee?

Solution – Buying Committee Completion and Engagement

• Implement a “Buying Committee Completion” initiative where BDRs and marketers collaborate to identify at least 5 key stakeholders for each target account before any outreach begins.
• Create a template that includes roles like economic buyer, user buyer, technical evaluator, and internal champion.
• Map buying committees for target accounts using tools like LinkedIn Sales Navigator, create persona-specific content, and track engagement at the account level
• For top 50 accounts, develop account-specific microsites with tailored content for each stakeholder role, tracking engagement by role rather than just by account.

4. Demonstrating Marketing’s Value to Leadership

Marketing leaders often struggle to prove impact in business terms executives understand. Our research suggest that while most CEOs appreciate the contribution that marketing makes, few are convinced about the ROI.

Solution – Marketing Impact Report

Translate marketing metrics into revenue impact and demonstrate how marketing-influenced deals close at higher rates with larger deal sizes.

• Create a quarterly “Marketing Impact Report” focusing exclusively on business outcomes.
• Include metrics like:
  • “Marketing-influenced deals closed 23% faster than non-influenced deals,”
  • “Accounts engaging with 3+ pieces of thought leadership content had 31% higher ACV,”
  • “Webinar attendees converted to opportunities at 2.8x the rate of non-attendees.”
• Present findings in financial terms (dollars, not percentages) whenever possible.

5. Pipeline Stage Bottlenecks

One of the most frustrating pipeline optimization issues is when deals stall at specific pipeline stages, extending already long sales cycles.

Solution – Launch a “Stage Acceleration Program

Analyze stage conversion rates to identify bottlenecks and create stage-specific content and programs targeting these trouble spots.

• Launch a “Stage Acceleration Program” focused on your weakest conversion points.
• If demo-to-proposal shows the most significant drop-off, create a specialized content kit for sales that includes customer case studies tailored to specific personas, ROI calculators, and competitive differentiation guides.
• Track the conversion improvement after implementing these resources and continuously refine based on results.

6. Fragmented Technology & Data

Few of us have the luxury of a seamlessly integrated sales and marketing data source. More often than not, essential information lives in disconnected systems (CRM, marketing automation, intent platforms).

Ideally, you implement integrations between systems and consider specialized attribution platforms like Dream Data to connect disparate data sources.

Solution – Conduct a “Data Journey Mapping”

• Conduct a “Data Journey Mapping” exercise where you trace how a prospect’s information flows through your tech stack from first touch to closed deal.
• Identify where data gets lost or siloed. Invest in a middleware solution like Dream Data or create custom integrations for the most critical connection points.
• Assign a “data steward” to monitor the quality and completeness of records between systems.

7. Converting Marketing Activities to Pipeline

One of the most common pipeline optimization issues is when high marketing engagement doesn’t always translate to opportunities and revenue. Accounts engage with content early in the buying process but don’t convert. We have all seen it.

Solution – Content Impact Matrix

Focus on total pipeline contribution rather than marketing-sourced pipeline, and align content to specific buying stages and decision-maker personas.

• Create a “Content Impact Matrix” that maps your existing content assets against pipeline stages and buyer personas. Identify gaps where critical decision points aren’t supported by content.
• Develop 2-3 high-value assets specifically designed to address these gaps.
• Track engagement with these assets and their correlation to pipeline progression, sharing results monthly with sales teams.

8. Low Close Rates

Healthcare is a more challenging market to sell in than many others, and the complex sales environment can often yield low close rates (often under 20%).

Solution – Deal Strength Index

Implement qualification frameworks like MEDIC scoring, focus resources on high-probability deals, and establish transparent disqualification processes.

• Develop a “Deal Strength Index” incorporating MEDIC scoring (Money, Economic Buyer, Decision Criteria, Identify Pain, Champion) that assigns a 1-100 score to each opportunity.
• Make this score visible in CRM dashboards and reports. Establish a threshold score (e.g., 60+) for resource allocation.
• Formalize a disqualification process for lower-scoring opportunities, creating a graceful “nurture return” path rather than simply abandoning them.

9. Resource Allocation Between Acquisition & Retention

So many marketers are stretched to do more with less. Pipeline optimization can seem like a huge hill to climb. With limited marketing resources, how do we balance new customer acquisition with retention/expansion?

Solution – Growth Source Analysis

• Analyze lifetime customer value and determine optimal resource distribution based on growth drivers (new logos vs. expansion revenue).
• Implement a “Growth Source Analysis” that quantifies exactly how much revenue comes from net new customers versus expansions over rolling 12-month periods.
• Calculate the marketing cost to acquire versus expand and the time to recover that investment.
• Create a visual resource allocation model that executives can adjust, showing how shifting budget between acquisition and retention affects projected revenue.
• Use this model to gain consensus on resource distribution.

10. Digital Asset Management Throughout Sales Process

As marketers, we go the extra mile to craft content and messaging that maps to the buyer journey, but we have very little control over what buyers read and watch and when they do that. As a result, content that could help target buyers gets lost in email chains and disconnected systems during lengthy sales cycles.

Solution- Digital Deal Room

• Launch a “Digital Deal Room” pilot with your top 10 active opportunities.
• Implement deal room software like Paperflite to organize sales content, track engagement, and create a single source of truth for each opportunity.
• Include all relevant content, proposals, case studies, and recorded demo sessions.
• Track which stakeholders engage with which content.
• Create a “Deal Room Engagement Score” that predicts close probability based on content consumption patterns.
• After the pilot, use the results to establish best practices for broader implementation.

We hope that these ideas help you on your way.

Watch the full episode

If you liked this post and want to learn more…

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