Unlocking the Potential: A Strategic Guide to CE/SaaS Academy Continuous Annual Planning

by Chris LoDolce

"We're underfunded, under-resourced, underutilized, underappreciated, we can be so much more if only "they" let us."

This sentiment echoes through the corridors of the industry, yet not all CE/SaaS Academy leaders share this view. The distinction between average/good and great CE/SaaS Academy teams lies in their Program Leaders' strategic approach to annual planning and the ownership they take in the process.

Here's what the leaders of these great programs understand and do well concerning annual planning.

1: They are constantly seeking out and gaining clarity on the organization's 3-5 year business goals and the assumptions being used as a framework for achieving those business goals.

2: They approach annual planning not as a Q4 event but as an ongoing process throughout the entire year.

3: They have taken the time to understand annual planning as a discipline and how annual planning happens at their organization.

4: They have a holistic view of their stakeholders across all departments. Not just their names, but their financial models, associated metrics (assumptions) they are responsible for, and the strategy/plays the stakeholder and their team(s) are implementing.

5: They have a pragmatic view of how their stakeholders view their Customer Education/SaaS Academy program. This means they understand the program's role in the 3-5 year business goals, the assumptions the teams are tied to, etc.

When a program leader understands and executes the above it unlocks nearly unlimited potential for collaboration and organizational impact.

Once you’re using the operational plan you developed, it’s time to begin regularly connecting the dots between stakeholder needs and educational content use cases that can assist departments and teams in delivering on their KPIs throughout the year.

We've taken the Stakeholder Management workbook we use with clients and in our cohort training and are providing it along with the necessary insights, information, and steps necessary to win annual planning throughout the year.

Clarity on Business Goals

Understanding and aligning with your organization's 3-5 year business goals is the cornerstone of effective annual, quarterly, and monthly planning. It's not just about knowing these goals exist; it's about integrating them into the DNA of your CE/SaaS Academy program. 

Dive into the Organizational Blueprint

The first move is to become intimately familiar with your organization's strategic blueprint. This involves attending strategic planning sessions and engaging in conversations with key stakeholders. If you’re unable to join the live planning sessions, see if you can gain access to slide decks, ask for a recap, or encourage your key takeaways to be posted on an internal wiki. Look beyond the surface-level goals and seek a deeper understanding of the philosophy driving these objectives. 

  • What values does your organization prioritize? 
  • What market trends are they leveraging
  • What challenges are they anticipating?

Connect the Dots

Next, connect the dots between the overarching business goals and the role your CE/SaaS Academy program plays in achieving them. Identify the specific contributions your program makes and the impact it has on the organization's success. It’s time to get involved in collaborating with leaders from other departments to understand how your program aligns with their strategies and objectives.

Uncover Assumptions

Every long-term plan is built on a set of assumptions. Identify and scrutinize these assumptions. What assumptions are being made for how education is being used in your organization? Not only how it’s being used but how departments and teams are defining and thinking about education. Are these assumptions realistic? How might changes in the industry or internal dynamics affect them? By understanding the assumptions underlying the business goals, you'll be better equipped to adapt your program to evolving circumstances.

Align Your Program Metrics

Your program's success should be measured in alignment with the broader business objectives. Ensure that the metrics you track directly contribute to the organization's 3-5 year goals. This alignment not only demonstrates the value of your program but also makes it easier to showcase its impact during annual planning sessions.

Explore the importance of treating annual planning as a continuous, year-round process. Stay tuned for insights on how to make annual planning a dynamic and proactive aspect of your CE/SaaS Academy leadership.

Communicate and Iterate

Clarity isn't a one-time achievement; it's an ongoing process. Regularly communicate with key stakeholders to ensure that your understanding of the organization's goals remains accurate and up-to-date. Be open to feedback and be ready to iterate your approach as the business landscape evolves.

Mastering Annual Planning as a Discipline

View annual planning as a disciplined practice essential for driving success. Great CE/SaaS Academy leaders don't view annual planning as a bureaucratic task; they see it as a disciplined practice essential for driving success.

Deep Dive into Organizational Processes

Immerse yourself in your organization's planning processes. Familiarize yourself with frameworks, methodologies, and decision-making structures unique to your company. This includes gaining insights into how financial planning, resource allocation, and risk assessment are conducted. The more intimately you understand these processes, the better equipped you'll be to align your program with organizational goals.

Build a Robust Annual Planning Framework

Craft a comprehensive framework tailored to the nuances of your CE/SaaS Academy. Clearly define roles and responsibilities within your team to ensure everyone understands their contributions to the annual planning process.

Establish KPIs for Planning

KPIs for KPIs. Very meta. Just as you set KPIs for your program's performance, establish KPIs for the annual planning process itself. Set KPIs for the annual planning process itself. Monitor the efficiency, accuracy, and effectiveness of your planning activities. Regularly assess and refine your planning KPIs to continuously enhance the discipline and impact of your annual planning efforts. Evaluate whether the planning process is contributing to strategic alignment and driving positive outcomes.

Cultivate a Culture of Planning Excellence

Foster a culture of planning excellence within your team. Emphasize the importance of strategic thinking, collaboration, and adaptability. Annual planning shouldn't be the sole responsibility of a select few; it should be ingrained in the culture of your CE/SaaS Academy.

Cultivating a Holistic View of Stakeholders

Great CE/SaaS Academy leaders understand that success doesn't happen in isolation; it's a collaborative effort that requires a deep understanding of stakeholders across all departments.

Identify Key Stakeholders

Identify key stakeholders within and outside your department. Stakeholders extend beyond titles; consider individuals who may not have a direct connection to your program but can influence or be influenced by its outcomes. This includes individuals from sales, marketing, product development, customer support, and executive leadership.

Stakeholders' Goals and Metrics

Understand stakeholders' financial models and associated metrics. Align your program's objectives with the broader financial goals of each stakeholder. For example, if the Marketing team is focused on lead growth, showcase how your Academy program contributes to driving more qualified traffic and MQL opportunities.

Strategy and Plays

Gain insights into the strategies and plays each stakeholder and their teams are implementing. Position your program as a valuable ally in achieving shared objectives. How does your program fit (or how could it fit) into their larger game plan? You might find that they haven’t thought about how an Academy program will fit in, and that’s okay. It’s your role to help them understand how your program will help accelerate their strategy and plays. 

Integrate Stakeholder Perspectives

Incorporate stakeholder perspectives into your planning and decision-making processes. When stakeholders see their input valued, they are more likely to be advocates for your program.

Feedback Mechanisms

Create feedback mechanisms that allow stakeholders to provide input on the impact of your program. This builds trust and positions your CE/SaaS Academy as a responsive and adaptable partner.

Continuous Year-Round Planning

Approach annual planning not as a Q4 event but as an ongoing process throughout the entire year.

Constant Monitoring and Adjustment

Regularly review program metrics and KPIs. Implement a system for real-time adjustments, ensuring your program stays aligned with organizational goals.

Regular Check-ins with Stakeholders

Establish a routine of check-ins with key stakeholders. Foster frequent discussions to gain valuable insights into evolving priorities and challenges.

Strategic Alignment Meetings or Workshops

Organize meetings or workshops and strategy sessions at regular intervals. Encourage cross-departmental collaboration to enhance strategic alignment and strengthen relationships.

Scenario Planning

Anticipate potential shifts in the business landscape. Develop contingency plans based on different scenarios, allowing your program to navigate uncertainties and opportunities that arise throughout the year with agility.


By following these strategic steps, you'll not only enhance your annual planning process but also unlock the unlimited potential of your CE/SaaS Academy program. Remember, success is not just about what you do; it's about how well you collaborate with others to achieve shared objectives. 

Click here to download the free workbook to get your continuous annual planning in order. 50+ uses cases on how to apply customer education to departmental and team goals to follow!

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