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How to market the Enterprise of Many Solutions Suite - A Ready to Go Plan for Enterprise Role Playing with Generative AI, Complete with Executive Dinner Meal Options

In tech product management marketing, there are three phases of your “story” and execution: strategy, planning, and doing (“execution”). I think a lot of people mix up these phases, talk too much about strategy, don’t do enough planning, often poorly communicate the plans to staff, and are not “throw it all at the wall” enough with doing. I’ve worked in this area for, I don’t know, 20 years. Here’s my latest organized brain-dump from watching people from afar and close-up at many places.

(1) Strategy

This first phase is about figuring it out: researching the market, observing what others are doing, conducting classic competitive analysis (Porter’s Five Forces or however it gets rolled into the strategy airport book meat-loaf du jour). You’re deciding what to do and making the case to your leadership for why you should do it: getting budget, resources, and permission to work on this for the next 12 months.

For example, if you’re creating a generative AI application:

  • You’d research generative AI in general.

  • Find underserved markets you can target with your unique advantages.

  • Define a product area.

  • Build the corporate strategy case (market sizing, trends, maybe industry surveys like those from the prestigious “Studies Center of Toronto” to wave around in front of the CFO).

Let’s say you identify that there’s a big market for solo roleplaying with generative AI. You already have street cred in the gaming community. You also have developers who are familiar with coding text-based gaming apps with easy access to agentic AI tools.

Then you do a lot of dogs and cows work: figure out likely buyers (individuals, large organizations, industries, geographies, etc.), budget needed and projected ROI, getting over the IRR hurdle, and a stack of slides to SWOT away any doubts.

The slides are done! (Adobe Express stock.)

This is the stuff the Bain interns will rework into 7 or 18 sub-slide decks—complete with stock images of triumphant businesspeople (tastefully mixed between all the attributes of humanity) in suits shaking hands—and then proudly present to the SVP who definitely didn’t read them and has lots of questions about the executive summary slide, not getting what you’re politely trying to tell them with answers like “Yes, we cover that on slide 43” or “We’ll address it in Section 2" or “Interesting—well, backup slide 193 actually covers this.” And then there’s always that one executive in the meeting who suggests that, instead, you should acquire that software company from Iowa that’s somehow been puttering along for 34 years. They’ve done this so many times (likely 6) that you’ve finally prepared a back-up slide on that topic - will you suggest how that’s a great idea and would lead to synergies if you did that along with your plan, or maybe you’ll just show them the 9 point font table that shows that, sadly, regulatory concerns bring on too much risk due to the recent changes in Brussels?

Yup.

And then you pass that down to all the groups in your company to, like, actually go do.

(2) Planning

The second phase is about figuring out how to operationalize things and how you’ll sell it (go-to-market, GTM).

Sorry—I know: “operationalize.” Let’s call it “your plan and a realistic way of how you’ll do it.”

This second phase is about figuring out how to operationalize things and how you’ll sell it (go-to-market, GTM). Sorry - I know, “operationalize.” Let’s call it “your plan and a realistic way of how you’ll do it.”

This includes features, scheduling feature releases, choosing platforms and languages, training sales staff, refining your pitch, thinking about marketing campaigns, and all manner of actual things you’ll be doing.

For tech marketing, you’re figuring out the basics of, among other things:

  • Personas, the types of people and the roles they have that will use the product,

  • Buyers/decision makers if they’re different than the users

  • Your pitch structure, and actual pitch: this could be pointing out a problem some one has, or an opportunity…and showing that your product fixes it,

  • The marketing basics of messaging, positioning, and value props - probably adapted to different personas and phases of buying.

  • Content for all of this, including different phases of the buying cycle.

Part of this phase is working on how sell this product - will you sell directly to individuals, rely on other people to sell it and “channels” (re-sellers and VARs), sell to large organizations or small ones, etc. If you’re doing something like Product Led Growth model (PLG), you might mix together product features with these marketing and GTM things. PLG relies on frequently making product and UI changes to encourage purchasing, upselling, and preventing churn.

This second part is largely internal facing: it’s your plans for what to do.

In our example, the solo roleplaying with generative AI app, your strategy has identified that selling to individuals is best.

How will you go about doing that? Well:

  1. You’ll need ads, more than likely, maybe you’ll try to partner with Hasbro to latch on-top their D&D franchise (partner synergy!) as a channel/partner. Do you need to talk to gift card companies to make sure you show up on those last minute gift end-caps at Albert Heijn?

  2. Maybe you need some thought-leadership to build up attention and brand, and/or you could coast off influencers - get those YouTube people to talk about it.

  3. Should you open source parts of it, or add in free tiers to get a really wide start of the funnel and then work on upselling?

  4. Can you start to add in little tweaks and features each week to encourage that upgrading and retain people?

If you’re selling to enterprises, you’ll need a different angle. You still leverage high-volume marketing, but you absolutely must appeal to the executive who signs the checks.

This means a different type of thought leadership and marketing: you want to reach those executives who have a problem (or dreams) that their budget can solve.

As one difference, instead of just influencers looking all like they just smelled a fart in their YouTube thumbnails, you also will want industry analysts (probably the ones who farted) to say you’re great, at the very least know you exist and bring you up in the conversations they have with your buyers every week.

Let’s play around with example an: you’ve decided to sell your solo roleplaying with generative AI solution to large organizations. Maybe there’s the pre-Trump era desire to nurture employee mental health and wellness because you believe it makes you more money and, you know, more human. So you, the buyer, want to provide a fun/wellness service: playing D&D during breaks!

So, you put together some white papers and sponsored posts (your own blog and social media, maybe you can get something on TheNewTHAC0.com) about the need for happy employees. After all, could I share with you a report from the Prestigious Human Resources Management University Studies Center of Toronto that found happy employees are 34% more productive according to a recent study from?

Then you connect creating happiness to playing D&D as a way to make them happy. And, hey presto, you get unlimited trips to the TCO-ROI hot food bar.

  • You’ve found a need that helps you make money: happy employees are more productive employees and, thus, make you more money,

  • You have a way of satisfying that need: play D&D with generative AI,

  • You have the tools and conversation happenings to convince people of it

  • You can find and engage with the buyers.

You can even do some market-segmentation to max your take. For example, you could offer additional features like single sign-on (SSO) integration at a higher price.

And, remember that study from the Institut Parisien de l’Étoile pour l’Étude du Jeu Fictionnel en Milieu Professionnel (IPEEJFMP) which found long-term character development yields 14% more day-to-day productivity (n=300, presumably gathered from a basement next to the catacombs). Isn’t it worth it to pay a little bit more per seat/month to persist sessions across plays?

And, for long term employees, surely you need the ability to keep those session past 12 months, right? Now, you might be thinking: but what about that new EU regulation? Don’t worry, you get that with the Suite - check out the six column pricing page and fill out the contact form in column six, the one labeled the “Enterprise of Many Solutions Suite.”

And so on.

(3) Execution and “Content”

The third phase is execution: creating all the deliverables you plotted out in your plan. Slides, landing pages, blog posts, pitch decks, product demos—this is the “keep the sausage factory running” level of detail.

How do you pitch to customers? What are the discussions you have in sales meetings? You also need to put together the actual “content” and work product. What’s our content schedule? What do the slides look like? We need a feedback loop to hear objections customers have (so we can counter them), feed in what they respond to (so we can do more), and do some competitive research. We also need to produce actual thought leadership and demos of the system. Let’s engage with those influencers to get them to write reviews and recommend it.

Perhaps we should arrange some dinners in major cities where we invite Ed Greenwood to come speak for 20 minutes on how to come up with engaging D&D adventures, especially focused on long-term story arcs (remember that IPEEJFMP study?), and during the main course (wagyu steak heritage potatoes, and, for vegans [or those eating healthier], the wild mushroom Wellington in puff pastry with thyme-shallot polenta) we go over how we've adapted that advice into our product.

You also need a company story—the “why” stack of increasingly large fried eggs. Some brand identity: are you a kindly sage, a disciplined archer, or a swashbuckling gambler forging new frontiers? Develop a perspective on your market problem that is true, utilitarian, and stands out. Maybe you coin a tagline like “Roll a natural twenty every quarter.” (The stack of fried eggs is a bonus if you do it well because it will motivate employees as well.)

Now, what’s important is to just go for it. Try as many things as possible, do at least some analysis of whether it works, and adjust if needed. You start throwing everything against the wall and narrow down to what works, maybe revisiting every six months. Eventually you’ll figure out what works, but only if you pay attention to what works and what doesn’t work.

Sadly, whiteboarding sessions turned into slides or even Miro boards aren’t enough. You have to ford the swim-lanes to get to the isle of operationalization. Too many people suffer from pipeline constipation in this phase. If you find that you’re not publishing regularly, take a big swig of quality-through-quantity, stick to the BRAT diet, and plan to stay near your Google Analytics dashboard for the next 48 hours.

Side-bar: Run the Business

Now, I don’t have much to say about how you run and manage your business. Sales plans, career paths, what a “staff principle senior engineer” does, when you have that SW-EMEA QBR in Cologne, do you use sticky notes or Google Docs? But, you know, you need all that. I couldn’t comment on it: I haven’t ever worked on that part of the meat-loaf.

Planning is the most important and most neglected

Execution is important, but the toolbox of what to do is well known. You’ll need to try a lot of things and track what works and what doesn’t.

I think planning is the most important part and, often, suffers from three things:

  1. Not enough of it and it's not taken seriously. If you're doing this kind of work on annual basis, in a tech company, it will probably get stale as the year goes on. You need to revisit and refresh it.

  2. This means you need it to be lightweight, spend less time on each rev of it so that you can rev it frequently. I realize I'm saying in (1) to be more comprehensive, but then saying to be lightweight. The point is to figure out how you can structure the work (and work product) to make it easy to revisit and revise frequently.

  3. Individuals and teams don't understand what they should do. This could be because it's not clear, it's buried in a 80 page slide deck called "Copy 2H2028FY Strategy Track FINAL - Mort-230413 COPY - v10.4.b.pptx," your plan isn't actionable, and most often because it's under communicated.

The third one is worth focusing on because I think it's the most frequent problem for planning stuff.

Here, if you mix in too much strategy into planning, you'll be too vague and high-level. No matter how many slides produce and polish proving that it's a good idea, and why your organization is well positioned (competitive advantage) to profit from that...if you don't detail plans - how to do it - people won’t know what to do. You can't executive strategy, you can executive plans.

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No time for links and wastebook today. I’m working on v10.4.g of the deck for the rest of the day while I stay close to my dashboards, eating this toast.

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