Why Building Your Go-To-Market Plan Feels Like Planning for D-Day

“Your task will not be an easy one. Your enemy is well-trained, well-equipped, and battle-hardened. He will fight savagely. I have full confidence in your courage, devotion to duty, and skill in battle. We will accept nothing less than full victory! Good luck! And let us all beseech the blessing of Almighty God upon this great and noble undertaking.”

General Dwight D. Eisenhower
Order of the Day (D-Day) 

In March 1943, during World War II, a combined planning group called COSSAC (Chief of Staff Supreme Allied Commander-designate) was created to plan Operation Overlord, which included the largest amphibious assault in history, commonly called “D-Day.”  COSSAC had a threefold task: plan a major amphibious assault on France, plan diversionary operations to keep the enemy off balance, and plan for the remote possibility of the enemy’s sudden collapse. Though D-Day ended with heavy casualties, it is considered an incredible success, the culmination of intricate and thoughtful planning.

Despite the ultimate success of Operation Overlord, the first days were challenging and fraught with failure; most objectives were unmet. Stephen Ambrose described just one D-Day landing site: "For a start, the objectives were wildly optimistic, especially for men going into combat for the first time. They were late hitting the beaches. The high tide and strong winds hampered the landings. The obstacles were more formidable than expected. The air and sea bombardments had been disappointing. The schedule for landing was too tight,“ and so on. 

Like COSSAC, SaaS Leaders face significant challenges when building their plans. Though not life and death in nature, good SaaS go-to-market plans are detailed and intricate. Whether making the initial plan for a new entity or laying the foundation for the next fiscal month/quarter/year, leaders will face unexpected headwinds and obstacles. Targets for pipeline creation, bookings, revenue, and profit may be “wildly optimistic.” Some campaigns will be ineffective, competitors will be more formidable than expected, and schedules will be late. Cross-functional leaders will disagree on how to resource some (if not all) objectives. Unlike COSSAC, most SaaS leaders do not have months and months to plan, nor do they have the luxury of amassing resources at scale months or even years before executing their plans. Nonetheless, SaaS leaders can learn much from the successes and failures of June 6, 1944, and the succeeding weeks and months.

#1: Cross-Functional Planning & Cooperation

Cross-functional planning, cooperation, and communication are critical. Before D-Day, a massive effort was undertaken to align the Allied Forces' naval, ground, and air operations. The effort spanned the militaries of many countries, including the United States, Great Britain, Scotland, Ireland, Canada, Australia, Belgium, Poland, and more. SaaS leaders need to plan cross-functionally as well. While this may sound incredibly basic, it is astounding how often Marketing, Product, and Sales are out of sync. Are functional leaders building plans together or in parallel silos? Are definitions consistent across functions? Are cross-functional processes understood and documented? Does each operational leader understand the whole of the plan? Do they know which components of the overall plan specifically depend on their teams’ deliverables? Asked another way, is every functional leader aware of and accountable for their deliverables' impact on the broader organization?

#2: Quality Data, Agreed Upon

COSSAC was planning for an unprecedented event – the largest amphibious assault in history. They were preparing for something that hadn't been done. In the world of SaaS and recurring revenue, every planning cycle can feel unprecedented. Senior leaders are evaluating many variables, from the macro (ex: global economy) to the micro (ex: projections for individual campaign effectiveness). Investment decisions are based upon incomplete – and potentially inaccurate – information. Even worse, decisions are made based on conflicting data. The source of truth for Sales may be different from Marketing. What one team calls a “good lead” may be called a “waste of time” by another. SaaS leaders must align and organize data to ensure all parties agree on that data's correctness, quality, and effectiveness. All parties must also understand the cross-functional impacts of meeting or missing their targets. Well-organized data must drive decision-making; all should work from a single truth source. 

#3 Acquiring Talent & Aligning Capacity to Plan

In 1943, the American Selective Service System (the “Draft”) fed COSSAC the warfighters it needed. Counterintuitively, planners sought inexperienced soldiers rather than combat veterans. Pvt. Carl West stated that raw recruits were required because “A veteran infantryman is a scared infantryman” and thus less inclined to storm the beach unthinkingly. Start-up and early-stage companies need to build and train their teams quickly but lack the luxury of the Selective Service System. Finding top-quality, experienced talent is hard enough. Knowing WHEN to hire that talent is even more challenging. How do I fit the new Seller into our financial plan? Can we generate the pipeline needed to support that Seller? How quickly will the Seller deliver bookings? How much will the Seller deliver? Is hiring one high-cost, experienced seller or two less experienced sellers better? Which roles should be prioritized? Many questions must be answered, and historical experience must be understood. Whenever possible, leaders must use quality historical data to drive capacity decisions.

#4: Plan from the Bottom Up

According to Pvt. John Barnes of Company A, 116th Infantry, the D-Day invasion plans seemed so well organized that “nothing could go wrong, nothing could stop it. It was like a train schedule, and we were almost just like passengers.” In reality, D-Day had many delays, and almost every goal was missed in the early days of the invasion. This feels eerily similar to many SaaS planning exercises. Leadership distributes a top-down plan that includes untested assumptions made with limited or suspect data and many unknowns. Then, there is shock and embarrassment when goals are missed, and teams dive into problem-solving to close gaps. Our D-Day heroes had the fog of war as a backdrop for their misses; modern SaaS leaders should have greater clarity. For SaaS leaders, the solution is to build a high-quality, bottoms-up plan. The plan should be created collaboratively and cross-functionally. Assumptions should be tested, and data should be validated and agreed upon by all stakeholders. The bottoms-up plan should stand up to deep scrutiny and be used to identify needed investments to close the gap between the bottom-up and top-down plans. Most importantly, the plan and its goals should be living and visible. Daily management is critical.

#5 Work Together to Respond to Unknown Unknowns

D-Day obstacles included concrete structures (pillboxes), machine guns, mines, barbed wire, etc. Allied Forces planned for these obstacles and were able to work through them, albeit at tremendous sacrifice. One unknown obstacle was the hedgerow. Hedgerows were mounds of earth dating to Roman times, covered in vegetation, reaching up to 16 feet in height. Operating independently, Infantry and Armored forces struggled to overcome these unknown obstacles. Facing heavy losses, Infantry and Armor learned to work together, thus overcoming the hedgerow challenge. SaaS leaders must shed protective instincts for a go-to-market plan to work effectively. Finger-pointing, protectionism, and defensiveness cannot get in the way of problem-solving. Once a plan is deployed, leaders must monitor progress, identify challenges, and react to those challenges cross-functionally, collaboratively, and without blame. Cross-functional collaboration will largely define whether the plan succeeds or fails.

Bottom line? Building a SaaS go-to-market plan is not easy, and executing the plan is even harder. To succeed, SaaS leaders must align the bottoms-up and top-down plans. Gaps must be filled, and teams must work together cross-functionally from a common dataset and a single source of truth. The plan must be built to win the war, not just the battle. Operation Overlord was not about securing a single beachhead. Don’t let your planning horizon be defined by the month or quarter – plan to win the war.

{Author’s Note: This post is long and was fun to write. Thank you for reading this far. I am interested in the history of World War II and have read much about it. Most every quote in the post came from the Stephen Ambrose book entitled D Day: June 6, 1944: The Climactic Battle of World War II, published by Simon & Schuster. For the Eisenhower quote, I also accessed Operation Overlord: From Concept to Execution, Naval History, and Heritage Command, accessed August 4, 2023, <https://www.history.navy.mil/browse-by-topic/wars-conflicts-and-operations/world-war-ii/1944/overlord/overlord-planning.html>.}