Adrian Pearce
Business Value Consultant, Thales Sentinel Software Monetization
Introduction
For software providers, growth today depends on more than innovation or engineering excellence. True scalability comes from a deliberate and data-guided approach to software monetization—one that aligns technology, business models, and organizational strategy. Whether your organization is shifting from perpetual licensing to subscription models, exploring usage-based billing, or introducing hybrid revenue streams, success requires more than technical execution. It requires cross-functional vision alignment.
Based on extensive experience supporting global enterprises through their software monetization journeys, this seven-point roadmap outlines a go-to-market strategy for those tasked with it, such as product managers. Using this guidance, they can create the clarity, structure, and agility required to achieve sustainable revenue growth with software. Below are the seven points.
1. Create the Strategy for Your Vision
This might seem obvious, but when it comes to software monetization, many organizations skip the step of establishing a strong vision and instead dive directly into technical implementation. They’ll address license design or entitlement management without defining the broader strategic intent. Yet, a well-defined vision should answer the fundamental why/what/how questions:
- Why are we transforming our monetization model?
- What value will this create for our customers and the business?
- How will we measure success?
Without these answers, projects tend to lose direction, and teams fall into cycles of experimentation without progress.
Your software monetization strategy should directly align with corporate growth goals—whether that means expanding into new markets, increasing recurring revenue, or improving customer lifetime value. Use the SMART framework (specific, measurable, achievable, relevant, time-bound) to ensure your objectives are actionable and trackable.
Rather than stating, “We aim to generate 50% of revenue from subscriptions within three years,” articulate the rationale: “We aim to shift 50% of revenue to recurring subscriptions within three years to stabilize cash flow, improve predictability, and increase retention.”
A clear vision is the compass for every subsequent decision—from pricing design to technology selection—and provides a consistent framework for stakeholder alignment.
2. Strong Ownership and Governance
Software monetization initiatives span multiple departments (see Section 3 on this topic), which makes accountability complex. To overcome this, two critical ownership layers must be in place:
- Executive Sponsorship: A senior leader who advocates for the project at the board or C-suite level, secures resources, and maintains visibility.
- Operational Ownership: A project or product lead who drives day-to-day execution, integrates business and technical perspectives, and ensures momentum.
Without executive sponsorship, projects risk stagnation as competing priorities and budget constraints arise. In contrast, when leadership champions monetization as a strategic imperative, it signals commitment and encourages organizational buy-in.
Strong ownership also ensures that decisions—such as product packaging, sales compensation, and system integration—are coordinated rather than fragmented. Governance mechanisms, including steering committees or program management offices, can further maintain alignment across global or multi-business-unit environments.
3. Build a Cross-Functional Monetization Team
Software monetization is not a task for a single department. Rather, it is a cross-functional initiative requiring expertise from product management, finance, IT, operations, and sales—because all these departments have a stake and need to be involved. Product managers must therefore act as orchestrators, ensuring collaboration across diverse functions.
A well-structured team includes:
- Product Management and Engineering, to define offerings, usage models, and licensing logic.
- Finance, to handle revenue recognition, recurring billing, and compliance.
- Sales and Marketing, to communicate value propositions and adapt go-to-market strategies.
- Customer Success and Support, to manage renewals and user adoption.
This collective approach prevents misalignment and late-stage surprises. For example, when sales teams are not informed about new licensing structures, they may resist change or miscommunicate value to customers. Early engagement mitigates these risks and creates a unified message across the organization.
Communication is the glue that holds this structure together. Frequent updates, transparent decision-making (detailing rationale), and shared documentation foster trust and collaboration.
4. Assess Your Current State and Define the Desired Future
Conduct an honest assessment of your current state—technologies, processes, pricing structures, and organizational readiness. Workshops that bring together representatives from each stakeholder group can be powerful. Encourage candid discussion about inefficiencies, unnecessary dependencies, and other pain points, while pointing out what does work well.
Once you’ve mapped the “as-is” landscape, define the “to-be” state as your ideal monetization model. Avoid simply replicating legacy processes in new systems. This is also the opportunity to harmonize and simplify some of your processes. Transformation should modernize, not mirror, the past. Challenge assumptions by asking “why” repeatedly:
- Why do we offer products and services in certain ways (i.e. the entitlements we provide)?
- Why do customers or market want to buy in specific ways?
- Why do we structure pricing as we do?
- Why do our competitors’ offerings succeed or fail?
These questions often reveal hidden opportunities to simplify, automate, or differentiate.
5. Stay Agile: Start Small and Think Big
Begin with a pilot project that demonstrates measurable value. For example, one software provider introduced a self-service portal offering a free product edition. Within months, they expanded their customer base, collected valuable user insights, and proved the viability of their new licensing model. The pilot not only delivered results but also built internal momentum for larger-scale implementation.
By breaking transformation into manageable phases, product managers can validate hypotheses, gather feedback, and refine approaches. Each iteration delivers tangible outcomes that reinforce organizational trust and secure ongoing investment.
6. Develop a Comprehensive Go-to-Market Plan
An effective go-to-market (GTM) plan enables strong execution. While most enterprises focus on the external launch—communicating pricing or packaging updates to customers and partners—internal readiness is equally important.
Within your organization, evaluate how the new monetization model affects sales compensation, finance operations, and customer support. For example, shifting from perpetual to subscription revenue impacts not only billing cycles but also how sales teams are incentivized. Align compensation structures early to prevent resistance and confusion during rollout.
Externally, ensure marketing and customer success teams can clearly articulate the value of your new model. Transparency reduces customer friction and helps reinforce the business rationale behind changes.
Use Case Example: Adobe
While initial backlash and revenue dips were unavoidable, a consistent strategic commitment ultimately transformed Adobe into a recurring revenue leader.
7. Measure, Analyze, and Continuously Improve
Many organizations treat post-launch evaluation as an afterthought. However, you can drive continuous improvement by establishing quantifiable success metrics before go-live, such as:
- Revenue targets such as annual recurring revenue (ARR)
- Churn rate
- Renewal rate
- Customer adoption
- Speed of delivery and update
- Customer satisfaction
- Staff satisfaction
After launch, routinely compare these metrics against the original objectives to assess:
- Did the initiative deliver the expected business impact?
- Were operational efficiencies achieved?
- Did customer satisfaction improve?
Equally important is qualitative feedback. Listen to your teams, customers, and partners to uncover early warning signs or new opportunities. Embrace a mindset of measure, analyze, and adjust. Even setbacks provide valuable insights that can refine the next iteration.
Software monetization, like modern product management itself, is inherently iterative. The organizations that succeed are those that treat it as an evolving lifecycle, not a one-and-done project.
Summary: Turn Software Monetization into Your Strategic Growth Engine
In a competitive enterprise software market, monetization is no longer a back-office concern. It is a strategic driver of growth and innovation. Product managers are at the center of this transformation, responsible for uniting technology, business models, and organizational alignment.
Software monetization success is not just about how you price or package your product. It’s about how you lead your organization to capture, deliver, and expand value at every stage of the customer journey.
By following this seven-point roadmap—anchored in vision, ownership, cross-functional collaboration, and continuous measurement—enterprises can transform monetization from an operational necessity into a scalable, customer-centric advantage.
Webinar
Watch the information in this blog discussed live! Catch our webinar, Achieve Software Monetization Success: The 7-Point Roadmap for Stakeholder Alignment with this blog author, Adrian Pearce, in discussion with Carsten Sckopke, Thales Software Monetization Professional Services Manager. Hear their exchange about how revenue generation, software protection, and customer satisfaction all hinge on the right monetization strategy.
See this webinar to further understand how to create a shared vision and establish a realistic GTM plan with all stakeholders aligned.
