How long is appropriate to plan for the initial implementation of the revenue strategy?

This will highly depend on what sort of headcount you have in place. In order to get basic infrastructure built it would take roughly a quarter to map out things like sales methodology, sales process, marketing philosophy, incentive compensation, etc. If you have a quarter to focus on flushing all of this out then you just need to hire to plan and execute.

The short answer: one quarter for the first actions to be making measurable impact. Anything longer can lead to demotivation and immobilization. Anything shorter and you risk blunders and blind spots, a launch with poor buy-in or asking for unrealistic resources / behaviours from the business.

The not-so-short answer: in my journey I’ve encountered enough strategy programs (and C Suites) to know the answer above can and should be pressure-tested. A few tips:

• Understand your C Suite’s sense of urgency: analyse how they articulate time horizons for similarly critical programs (e.g. large product releases, organization redesigns);

• Understand your company’s culture relative to bias to action vs. status quo magnetism. Identify and double down on change champions that will help clear your path;

• Lead with impact, even if small: pricing, payment terms or sales comp tweaks can create a quick lift, getting you execution credibility for deeper action (e.g. funnel overhaul, marketing reset). Starting from existential topics can be (and is often) met with incapacitating resistance;

• Be clear and aggressive with timelines: It is better to reprogram/re-partition execution later upon meeting acute constraints than to embrace a “let’s see how it evolves” mentality;

• Share merit and redirect the spotlight often, a strategy’s success is measured by its results and authorship will be established in the long run, not by stage minutes.

I don't think there is a hard rule for how long an implementation should take to launch a new revenue strategy, and each company and the degree of change will influence this significantly. I wrote a longer answer to a similar question about deciding what to do first (see "How do I decide which tactical piece to implement first in our strategy for revenue engine?") and I think that guidance can help you reach an better estimate for the C-suite. If you have a plan, understand the dependencies, and have a clear set of priorities you should be able to give them a good estimate. All that said, if you're taking more than 6 months to have some initial implementation and traction with the changes, then it is probably moving too slowly.

There's a good book (How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything In Between by Bent Flyvbjerg) that is an easy and entertaining read about planning and managing big projects that might also have some useful pointers for you here.

One final pointer if you aren't already thinking about this is to try to line up the changes and launch to the beginning of a quarter/half so you can give new quotas, financial plans, etc. that all include the expected effects. This will make life much easier than a mid-quarter switch for everyone involved.

Building an estimate of the time it would take to implement a revenue strategy is indeed the million dollar question. To be honest, I also often ask my team the same thing. Here’s how we established some estimates:

Break the identification and implementation of the strategy into a few phases:

• Phase 1: Planning and Setup – it normally takes 1 to 3 months for all the details of the strategy to be finalized and all the systems need to be in place;

• Phase 2: Pilot and Initial Rollout – about 3 to 6 months when the strategy is tried with parts of the business to see how it operates in practice and to make some refinements;

• Phase 3: Full Implementation – lastly, based on the size and scale of the strategy, between 3 more months to a year, deploying the strategy across the board.

Taking into account the following key variables:

• Complexity of the strategy – the more complicated it is, the more time you will need;

• Resource availability – having limitations in terms of workforce, budget, or technology will also stretch the timeline;

• Organizational readiness – how well is the organization ready to start a new strategy. The setting of the milestones: the phases within and the stages for those when creating the structure of the estimated time.

For a full-cycle time from planning to full deployment in a moderate to large business, it would take between 6 months to a year. It demonstrates the reality behind the implementation of the strategy and permits to make some adjustments once we learned how the strategy settles in practice. This sort of structured approach provides the vital information for all levels of the organization while ensuring a clear grading of expectations.

Determining the right timeline for implementing a new revenue strategy hinge on various factors, including the organization's size, the complexity of the sales process, and the existing infrastructure supporting the go-to-market engine. it is so important to remember that perfection is the enemy of progress, as aiming for perfection can lead to delays and missed deadlines.

Stakeholders on your senior leadership typically will convey a targeted go-live date for the new strategy, as they base their commitments and resource allocations on this timeline. As the architect of the strategy, your role is key in understanding their perspective on the end state materializing. Work backward to identify key milestones and hurdles that need to be overcome by the deadline.

For instance, if the plan is to launch the strategy at the beginning of the fiscal year, you will need to ensure that critical components such as financial planning, organizational design, compensation structures, systems infrastructure, and enablement programs are in place. These are the "big rocks" that require careful planning and execution. Collaborating with stakeholders and business partners, you can break down these big rocks into actionable tasks and workstreams, taking into account the capacity of each team to deliver on their respective responsibilities.

This collaborative approach allows you to create a high-level project plan that outlines the pace and sequence of activities needed to meet the stakeholders' expectations for the go-live date. A good timeline is based on a deeper understanding of the milestones on the way. It allows you to be flexible with that timeline, as you can align with both stakeholders and business partners on the opportunity cost of additional changes, or how velocity can be ramped up by deferring some of the action items or big rocks altogether.

I will start off by saying that there is not a one size fits all approach to the implementation of a revenue execution strategy. The plan is dependent on the scope of the plan/program and the potential revenue impact coupled with urgency. My general rule of thumb is that a 1-3 month timeline is a reasonable approach.

Factors Influencing planning for initial implementation - 

1. Complexity: Needless to say, Complex initiatives require a different approach to launch as compared to straightforward ones. What defines complexity? 

• Number of moving parts: Is it a change or a transformation? A complex strategy with multiple elements e.g., product pricing changes, new product launch, new marketing campaign, a new rep facing AI solution, will require more upfront planning than a simpler one such as pricing tweak or a discount change.  

• Level of change required: A radical shift in your revenue model or a radical shift in your reps day/today will demand more planning and stakeholders buy-in compared to a minor adjustment.

• Regulatory/Governance pre-requisites: Are there any legal or compliance considerations that need to be factored in? Obtaining necessary approvals could add time.

2. Readiness: Is your company action-oriented or more cautious? Finding a balance between planning and taking action is key. Some things to consider to assess readiness -

• Team expertise: Does your team have the necessary skills and knowledge to execute the strategy? Training or hiring specialists might be needed, extending the timeline.

• X-functional Alignment: Sales, marketing, and customer success/support need to be on the same page for a successful rollout. Cross Functional  communication and planning add to the initial phase.

• Technology & infrastructure: Do you have the necessary tools and software to support the strategy (e.g., CRM, pricing tools)? Acquiring or integrating new tools could drastically impact the timeline.

• Data availability and quality: Reliable customer data and market insights are crucial for informed decisions. Collecting and analyzing data might add time upfront.

Learnings for setting a realistic timeline:

• ​​Pilot programs: For some initiatives, consider testing a small-scale version of your strategy to identify issues and refine the approach before full rollout. This might add some time upfront but can save time and resources in the long run.

• Start with small wins: Focus on initial actions that can deliver measurable results quickly. This builds momentum and demonstrates the value of the strategy.

• Be clear on timelines: Establish deadlines and milestones to keep everyone accountable.

• Be flexible: The initial plan might need to be adjusted as you learn and iterate. Implementing a new strategy often involves behavioral changes within your team. Factor in time for communication, training, and addressing resistance.

Remember, it's better to get started with a solid plan and iterate as needed than to be stuck in the planning phase for too long. Choose progress over perfection!