‘Tis the season for strategic planning! As B2B leadership kick off their team's annual planning sessions, pricing and packaging needs to be part of the conversation. Most teams often spend considerable time discussing growth targets, product roadmaps, sales capacity and tactics, and investment priorities. But more often than not, discussing pricing strategy falls off the radar or takes a back seat in the discussion.
In my experience, pricing is often addressed too late in the planning process, if at all — perhaps as simple as an annual price-increase decision, or something to revisit after other product roadmap and project priorities are settled. But minimizing pricing and packaging improvement discussions in annual strategy planning leaves a great deal of financial and growth upside on the table.
Pricing strategy should be part of the broader conversation about where your business is going, how it will grow, and how it will capture the ongoing value it creates through effective pricing and offer structures. As your team develops their 2027 plans, here are several key questions executive teams should put on the agenda.
Are We Capturing the Value Available Today?
Not every pricing opportunity requires a major redesign. For many SaaS and enterprise software companies, the most immediate opportunity is to determine whether prices still reflect the value being delivered.
Customer needs and value perceptions change, especially in today's fast-paced AI world. Products become more capable, delivering exceptionally better value. New use cases emerge. Yet many companies' pricing structures remain largely untouched, resulting in a proliferation of under-performing add-ons.
Consider asking:
- Does our pricing still align with the value customers receive?
- Are our packages and pricing metrics supporting the customer behaviors we want to encourage?
- Are certain customers, segments, or use cases materially under-monetized?
- Do our current prices support our growth and margin objectives?
- Are we adequately monetizing our supporting services?
- Have we engrained price increases into our process?
Before deciding what to change, it is worth understanding whether the existing strategy is still serving the business.
How Do We Plan to Best Monetize Our Innovation?
Features and innovation are being released faster than ever, particularly as AI accelerates product development. But more functionality does not automatically translate into more revenue or greater customer value.
Too often, monetization is discussed only when a new capability is nearly ready to launch. By then, important packaging and pricing decisions may already have been made indirectly through the product-development process.
As you review the 2027+ roadmap, ask:
- Which innovations create enough incremental customer value to support a new package, add-on, or pricing metric?
- Which capabilities should strengthen the core offering?
- Are we investing in features customers will value and pay for?
- Are pricing and packaging implications being considered early enough in the roadmap process?
A product roadmap describes what you intend to build. A go-to-market and monetization strategy explains how that investment will contribute to growth.
Is It Time to Redesign Our Offers and Packaging?
As features are released at a faster pace, companies should revisit whether their offers and packages still make sense for today's customers. The right packaging should also make it easier to monetize new features and AI capabilities as they are introduced throughout 2027.
For some companies, this may require fine-tuning. Do feature thresholds need to be refreshed? Should overage pricing change? Are the distinctions between packages still clear and meaningful? Do we need to start evaluating alternative (or hybrid) pricing metrics?
For others, particularly those that have not revisited packaging in several years, a more substantial redesign may be needed.
Consider asking:
- Does our good-better-best structure create a logical path for customers to grow throughout their journey with your solution suite?
- Are the right features (and respective guardrails) being used to differentiate packages?
- Are starter plans attracting and converting the customers we want?
- Can new innovation be incorporated without continually creating new add-ons and complexity?
- Does our portfolio support both new-logo growth and net revenue retention?
Effective packaging should help customers select the right offer today while creating a clear path to adopt more value over time.
Is It Time to Clean Up Legacy Plans?
Customer migrations require planning, resources, and careful management of churn risk. It's understandable that executive teams delay them. But repeated delays can leave a company supporting an expanding collection of legacy plans, packages, thresholds, add-ons, and customer-specific commitments.
Over time, that complexity can constrain Product, Operations, Sales, and Customer Success. It can make new features and AI capabilities harder to launch consistently, while leaving customers on older value propositions with no clear path to adopt the company's latest innovation.
Consider asking:
- How many legacy plans are we supporting, and what is that complexity costing us?
- Which customers remain on plans that no longer reflect our current value?
- Are older plans limiting adoption, expansion, or our ability to introduce new capabilities?
- Could a phased migration create a reasonable landing for customers while improving monetization?
- Are we missing financial upside with legacy customers who would be willing to pay to receive our latest value?
A well-managed migration is not simply a price increase. It can align pricing with current customer value, capture under-monetized revenue, simplify the commercial model, and create clearer paths for future adoption and growth.
Are There Other Tactical Pricing Opportunities?
Even a well-designed pricing strategy can underperform if it is not consistently executed. I frequently see meaningful margin leakage occurring through everyday commercial decisions rather than the published price itself.
Consider asking:
- Are we being too cautious with price increases at renewal — especially with customers who historically received preferential discounts?
- Are overages being monitored, communicated, and charged consistently?
- What do discounting patterns across salespeople, customer segments, and deal types tell us about our net pocket margins?
- Are approval policies preventing unnecessary discounting, or simply documenting it?
- Are sales teams effectively communicating and defending the value behind the price?
Recorded sales conversations, including Gong calls, can provide particularly useful insight. They can reveal where representatives lose confidence, introduce discounts too early, or struggle to communicate value — evidence that can support targeted price-realization coaching rather than broad sales training.
Improving pricing performance is not always about changing the strategy. Sometimes it is about helping teams execute the existing strategy with greater consistency and confidence.
Put Pricing on the Agenda
After more than 30 years in pricing, I've learned that meaningful pricing improvement rarely comes from asking one narrow question, such as, “How much should we raise prices next year?”
Including that question in the 2027 planning process may uncover opportunities to monetize innovation, redesign packaging, address legacy plans, reduce margin leakage, and strengthen commercial execution. Those opportunities are much easier to act on when pricing is part of the plan from the beginning.
