What are the aspects of operationalizing a Go-To-Market plan that might prove to be most risky?

I'll answer this from the aspect of a GTM plan for pricing and packaging changes. The top 3 areas to identify and mitigate risk around include:

1) RISK: Did you get the Price/Packaging right?  

• Does the price and what's included in the packaging resonate with the buyer? 
• Is the price point in the ball park of what the customer is looking for and relative to alternative solutions?

MITIGATION PLAN: Get input from customers, prospects, analysts and advisors in advance of the change and GTM roll-out.

2) RISK: Are your revenue teams (sales, CS, renewals, etc.) properly enabled?

MITIGATION PLAN: Make sure that you have all the mesasging, positioning and sales tools ready for the teams. Ensure that you have enablement/training time setup with all the teams. Certify them on the new packaging/pitch/pricing. Makes sure they are ready for objection handling and questions from customers and prospects.

3) RISK: Impact to existing customers (vs. net new)

MITIGATION: Map all of your existing customers to new packaging and understand difference in existing pricing and new pricing. Ensure that you have a plan for the timing of when existing customers will go to the new packaging? Will they transition immediately, or wait for renewals? Will you let existing customers grandfather on the old packaging and/or pricing? Are there contractual limitations on what you can change?

There are probably three major questions to answer when operationalizing a GTM plan: What is the governance? Meaning who is in charge? What is the division of labor? Who holds what decision rights (e.g., decide, influence, escalate)?

When do you scale?

There are two broad options: launch-and-learn or test-and-scale. In a launch-and-learn model, scaling happens first as the commercialization comes online across the enterprise at once. Learning then occurs after rollout and across the enterprise. This type of GTM implementation makes sense in a low-risk, high-resilience situation.

In a test-and-scale model, the innovations come online in pockets and pilots. Pilot learnings inspire changes to the plan, and the finalized plan is rolled out in waves. The test-and-scale model makes sense for implementing a commercialization strategy when external and internal resilience is low. It also makes sense when resilience is high but risk is also high.

And, last you need a framework.

In either scaling framework, what is the cadence of activities over the course of the implementation? I've used a 4-step process successfully:

1) Act on the plan

2) Measure the actions’ results

3) Share and discuss the results

4) Adjust the plan

One of the biggest risks of operationalizing a GTM plan is the lack of a common understanding of the time it takes to do good marketing work, internally.

Marketing shouldn't slow down product; but at the same time, the more time and advance notice marketing has, the more we're able to enrich, adapt, and customize a GTM plan appropriately. A GTM playbook is a best-case scenario and a guideline which has to be adapted rapidly and practically to the lead time available.

The marketing team for WordPress.com is relatively new (around 5 years old for a product almost 15 years old), and speed is very important to product development and serving millions of existing customers. Our engineering teams are pushing to production several times or even dozens of times a day, and so we have to work together to make sure we give sufficient time to amplify the great work they're doing with existing and prospective customers.

Ideally we're involved as soon as it's known the product team is preparing a feature or change for launch, so we can identify the channels, messaging, and timing needed to market the work as soon as it's ready to ship to production.

We don't use formal documents like a market requirements document, but I've documented and communicated top elements of that process the engineering team should be thinking about when they're preparing a feature for development, and it's an exercise they can go through at kickoff instead of when the feature is ready to test or launch. We can partner with them to identify any gaps, or help answer those questions, and then come up with a realistic GTM strategy with the time available. 

Here's an excerpt of the exercise I shared internally:

We’re building a feature or product to solve a problem or do a job for customers, and then tell as many of the right customers as possible that we’ve solved it for them.

- What product or feature is being developed? Focus on user perception and usage – features, needs, usability, methods of usage. How does it apply to customers of the entire family of Automattic products?
- Who are the target customers? What user behavior, demographics, or other attributes do they have? How might they be different? Does this apply to current or prospective customers, or both? A subset of customers?
- Why are customers likely to want this product/feature? (aka: what problem does this solve for the user? Why would they ‘hire’ it to do a job?)
- When will the product be available? How much detail can you share about the timing? Can you include any ballpark dates or checkpoint dates which could be helpful for those involved to know about?
- Any pricing-related information? Is the feature being added to a plan? Does it replace a paid feature, lower a plan price, or change the potential revenue from a sign-up?

Great question. There could be many reasons why a GTM plan is deemed risky. Perhaps because a lot is hinging on a product launch, or a risky marketing campaign and the riskiest of all - you as a PMM are not completely on board with the product. (The later should not happen but it has happened to many us, I assume)

IMO, the key is to 

1. Over-communicate: Define a DRI, make sure every stakeholder is involved, follow a decision-making model such as the one I mentioned above (RACI model). 

2. Plan plan plan: Have a mitigation plan B ready if your original plan fails, or perhaps even a Plan C if Plan B fails. For a recent launch campaign we did on Indiegogo, we had Plan Bs for every major marketing activity. 

1. Making assumptions about pricing and not vetting them with sales VERY early in the process
2. Assuming that its a 'handoff' to sales enablement vs in reality its an ongoing partnership where PMM needs to lean in quite a bit to help
3. Not factoring in global requirements VERY early on and discovering late in the game that its not just a 'localization' issue that will handled by the 'local' teams
4. Not factoring in migration or EOL requirements and just focusing on the new, shiny products. Customers have more heartburn about migrations than marketers account for. Be ready for that, and factor that heavily into operationalization

This is a great question because, as every PMM knows, each launch holds a surprise hiccup. If you can mitigate as much risk as possible before that time comes, then you’ll be successful in solving those last minute snafus.

Assuming your marketing brief and GTM plan are finalized and approved, a successful GTM execution comes down to organization, stakeholder alignment and (the hardest one!) seeing around corners.

Here are the riskiest components in each of those categories and how to mitigate that risk:

1. Lack of organization:

• Misaligned plans
• Losing track of documents and creative files
• Overly tight timelines
• Rehashing previous conversations

How to mitigate: Keep a source of truth document (or spreadsheet, my personal favorite) where you track every single launch component, including status and timeline, meeting notes, resources, channel plans and assets, launch day tick tock and more.

2. Missing stakeholder alignment:

• Vague R&R
• Lack of resourcing
• Unclear expectation-setting

How to mitigate: Bring your cross-functional and marketing partners along for the journey by pulling them in at key strategic milestones when you’re creating your plan, then holding regular status meetings up until launch through to a post-mortem.

3. Not seeing around corners:

• Lack of familiarity with the deployment tech
• Broken user journeys
• 11th hour feedback

How to mitigate: This one tends to be company-specific, so ask your colleagues about unexpected day-of discoveries on previous launches and then prepare for those specific scenarios. Also, it never hurts to build a buffer into your timeline and have an extra set of eyes on the creative before it goes out the door.

Operationalizing a go-to-market strategy is not for the faint of heart. There’s a lot that happens between writing the doc (see narrative above) or slides and executing the strategy in the market. Here’s my list of the riskiest elements and how I solve for them.

First, team alignment. In my experience, aligning the team is the trickiest element because the amount of stakeholder voices expands seemingly exponentially the closer you are to launching your GTM activities. This is just as true for the early stage pre-product market fit startup as it is for the hyper-growth, more mature company. My solution for this is constant cascading communications. The job of the Product Marketer is often to ensure that everyone is rowing in the same direction, so make sure that you are communicating often and bringing people into the process early. 

Like the above question about GTM plan fundamentals, I find that writing out the GTM plan in narrative form is extremely helpful, both for clarity of thought and as a handbook for new people joining the GTM process. I also find that consistent adoption of OKRs is a great way to help ensure the alignment of activities. Like many companies, we use OKRs at GitLab as a way to align our team activities with the company strategy and with each other. The process of creating, debating, calling out dependencies, and tracking progress is, itself, a way to create clarity on both what we are trying to achieve in our GTM strategy, how we will accomplish it, and who will take ownership of which roles and responsibilities.

Second, data data data. A key success factor is ensuring that everyone on the go-to-market team (marketing, sales, customer success…everyone) is using the same data, is following the same KPIs, and is looking at the same dashboards. 

Third, the market is not a constant – just as you are evolving and operationalizing your GTM, so are your competitors. It’s like when you look at a star in the sky, you are really seeing the light that emanated in the past. So too is the case with your GTM plan that was based on where your competition was at a previous point in time. My solution: tight feedback loops throughout the GTM team. This is an area that small companies have an advantage - since their teams are small, they can more easily have all the people in the room or zoom giving feedback on every aspect of the GTM process. While easier in a small company, tight feedback loops can work at scale if they are engineered into the process. I once rolled out a new positioning strategy in the market and learned that it was ineffective (see metrics answer above). While it was a bummer that the original positioning wasn’t effective, I was proud of the team for developing this insight quickly, rapidly rolling it back, and then iterating based on what we learned.

Almost every launch has something unexpected arise not matter how much you plan. To me, the riskiest items are the ones that might be harder to change or adjust post-launch.

1. Making sure there is product market fit is make or break. By that I mean, the buyer you've identified has a clear pain point and the product that was build addresses that pain point. I've seen launches across different companies struggle because a product was built before fully understanding the buyer need.
2. Lack of alignment on decision makers can derail a launch plan. If decisions makers and decisions that have been made aren't clearly communicated, you could accidentally move forward with the wrong GTM plan without even knowing. I've used the RACI matrix structure to define rolls as well as RAPID. It's not a very sexy topic, but can be highly effective.
3. Pricing is another risky item. If you don't properly research and test your pricing, your product could be underpriced (losing you money), overpriced (causing adoption issues), or could even have the wrong pricing model. 

The most risky operationalizations in a GTM strategy to me are spray and pray (homogenous) campaigns, broad (not segmented nor sophisticated/suppressed, not segmented (targeted) and not timely (saturated). Basically, if you are not intentional with your outreach that is a huge risk and you'll end up as noise, spam, or worse - blacklisted (and that is a huge risk).

The biggest risk I typically see in GTM strategies is that it doesnt work. Somewhere, something was missed, or the messaging, product, etc. doesnt resonate with prospects and customers. '

I have found that your webiste is a great place to experiment to ensure this doesnt happen. It has historical data to anaylze various aspects of your GTM strategy including verticals, personas, messaging, sales motions, customer marketing, etc.

Training the org is another big risk. If there is a new revenue-driving feature that CS/CSMs/SEs dont know how to technically talk about or sell, that new feature will fall flat.

Cross-functional collaboration, alignment, and execution are the most challenging aspects of operationalizing a GTM plan.

Challenge: X-functional collaboration

Solution: PMMs must ensure that a cross-functional team with clear roles and responsibilities supports every major GTM plan vs. chasing for support for every plan. A RACI framework will ensure your GTM plan is cohesive and connected across teams (e.g., your campaign will seamlessly drive traffic to your landing page, and leads captured through your page will flow to sales teams).

Challenge: X-functional alignment

Solution: PMMs should leverage DACI frameworks (driver, approver, contributor, informed) to help drive decision-making across cross-functional teams. An established DACI for large GTM plans will ensure the "why" behind big decisions is well documented, and x-functional partners can use the logic behind the decision to inform their respective efforts.

Challenge: X-functional execution

Solution: PMMs should leverage GTM checklists or project management software to keep track of the progress of GTM plan execution. I typically have a stand-in meeting booked with my x-functional partners on a regular cadence to keep track of the progress of any GTM plan. Meetings are an effective tool to keep teams focused on deliverables and troubleshoot emerging issues as a team.

Usually the most risky parts of the GTM plan are actually in the foundation: the why we're building this, the who we're building this for and the what the product value prop is. These three things are critical to your messaging/positioning, who you're targeting, your channels you're going to leverage, and what the expectations for this launch are. If you don't get early buy-in on the foundational elements of your GTM plan you may run the risk of building a plan based on misaligned ideas.

A few things come to mind—

• You get the audience wrong. You’ve built something you think will be useful, but your marketing and messaging isn’t tailored to the right audience, so adoption wanes.

• You get the pricing wrong. I think every pricing change will feel like you’ve gotten it “wrong” because you’ll hear the loudest feedback from what may be a minority of your buyers. But if you haven’t tested your pricing in smaller groups or done adequate interviews to get the packaging, model, price point, and discounting correct, you risk losing a large swath of existing users or turning away prospects that may not give you another shot

• You haven’t set up adequate tracking. You push something into the world and believe from a few conversations that adoption will be high, but you haven’t set measures of success or a plan to come back in the first week, 6 weeks, and 3 months to reassess.

To me it starts with right people to target (ICP) and the right message. I've talked about ICP in other answers so for this I want to talk about clarity and simplicity in messaging.

If you're not maniacally committed to simplicity and clarity in your marketing messaging, you're going to confuse your customers and prospects.

Think about it: You spend 30-60 hours a week (or more!) thinking about your company, its product, and mission—probably even in your off-hours if you're like me. 🙃

But your customers? They aren't dedicating anywhere near that much time. At Postscript, our customers tell us they spend 1-6 hours a week thinking about SMS. At Allocadia (my last company), people were only thinking about marketing budgets once a week or even monthly. Then in the Marketing Technology industry (where I've worked for awhile) there’s Scott Brinker's massive Marketing Technology Landscape with 14,106 companies in it this year… talk about overload. This is the same in all industries.

So, when you're crafting your messaging, challenge yourself to make it more simple and clearer. Your customers don’t have the time or attention to wade through the nuances—you need to get to the point fast. That's one of the biggest risks in your GTM plan, overcomplicating messaging.