At some point, almost every B2B business – AI, SaaS, even good old fashioned services – will make a decision to ‘go upmarket’ and try to start winning enterprise clients.<\/p>\n
I’ve seen enterprise done wrong plenty of times, both when consulting with clients and seeing what they were doing previously, but probably the most exposure I’ve had to organisations getting it wrong was at RevvedUp, where we’d speak to lots of organisations who either wanted to start ABM or had started but stalled. Every example in this article comes from real experiences of seeing enterprise marketing done well and done badly in organisations I’ve worked at, consulted at, or sold to.<\/p>\n
This piece is about one specific moment: when a startup decides it’s going to move upmarket and win bigger accounts. It follows the path I’d take a founder or CRO through, in order:<\/p>\n
<\/p>\n
<\/p>\n
<\/p>\n
<\/p>\n
By upmarket, I mean upper mid-market to enterprise. Typically that’s the top end of the five-figure ARR range, often going into six figures, and for some organisations all the way into the millions of dollars for an annual contract. Often they’ll start thinking about signing two or three year deals as well.<\/p>\n
There are usually three reasons a startup gets here.<\/p>\n
The first is pull. The product has matured enough that they start getting actual interest from the enterprise market. Maybe they’re doing well with lower to upper mid-market organisations, starting to get case studies and some good word-of-mouth referrals, and showing up to events that cross over with some of those bigger accounts. That inbound interest always piques the interest of founders, the board, and usually the CRO or VP of Sales, because of course everyone loves to get those lighthouse logos on board.<\/p>\n
The second is push, which is purely an internal decision. Maybe it’s aligned with a fundraise, and you model out how you’re going to go from 10 to 100 million, or 100 to 500 million, and you realise that doing that with 10k, 20k, 30k deal sizes is going to need an enormous volume of reps. The maths just tells you that you need to start breaking into enterprise accounts, and that’s really the only way you’re going to hit your overall revenue numbers without burning your market.<\/p>\n
The third, occasionally, is a massive overhaul of the product that suddenly fits enterprise much, much better.<\/p>\n
I’m focusing on the push factor here: you’ve just raised a round, or redone your annual forecast and planning, and you realise the only way you’re going to get to your number is by starting to break into enterprise.<\/p>\n
Sometimes businesses do struggle with targeting when they go upmarket, and I’ll cover that. But the bigger issue is the motion. Throwing AI at a mid-market motion and pointing it at enterprise accounts isn’t going to produce good results.<\/p>\n
What you have to do is redesign your go-to-market systems and motion for the enterprise. Once you have the right structures and frameworks in place, that’s where you can use AI to help improve the implementation of those plans.<\/p>\n
The first thing that breaks is the level of depth needed to break into an account, which is materially more than it is at early mid-market. Often the buying committee is significantly bigger, so you need to engage a lot more stakeholders, and they’re more dispersed. They can be spread across multiple time zones, offices and different reporting structures. Selling to an enterprise is sometimes quite a Byzantine exercise, so you also need to really deeply understand the account.<\/p>\n
The ability to translate your product and your solution into a clear roadmap, project and programme that can be understood by the stakeholders on their side requires a lot more solutions engineering or solutions architecting, and a lot more detailed documentation during the sales process, and even earlier than that.<\/p>\n
Trust, case studies and authority matter far more in enterprise than in mid-market. Senior careerists within an enterprise might have been in seat for 15, 20 years, and they don’t want to make a silly move. That’s where the phrase “no one ever got fired for hiring IBM” comes from.<\/p>\n
So any executive that signs off on bringing your solution in will be looking for air cover. Some of that air cover is being able to say, “Look, this is a credible organisation. They’ve worked with X, Y, Z,” and having all that social proof. It also means having you attend, sponsor and be front and centre at a lot of the major industry events, which is why field marketing is a more important thing for enterprise marketing than it is for mid-market.<\/p>\n
Often these enterprise organisations are in two or three year deals with another vendor, so it’s really important that they get to know you during that period of time. You can’t just pop up three months before the end of their contract, because probably they’ve already made a decision about who they’re going to go with. Having more patience and stronger views on nurture is very important.<\/p>\n
During the sales process, you need much greater rigour and structure in how you handle and manage the ongoing deal. Using something quite structured and deep like MEDDPICC becomes much more important in enterprise than in mid-market.<\/p>\n
Once you understand how different enterprise is, the next job is making sure the business is set up to survive the timeline. This is where I see founders make most of their mistakes in the first ninety days.<\/p>\n
One of the most common mistakes is probably not understanding how long enterprise marketing can take, and therefore setting false expectations and not having in place the right leading indicators that would suggest things are starting to move in the right direction.<\/p>\n
The reality is you’re not going to have closed-won deals on the cards for possibly up to twelve months, and certainly at least six months, after you start a concerted effort towards enterprise marketing or enterprise sales. Obviously, if you already have some deals in motion and that’s what triggered the idea, you should be closing those out. But if you’re starting completely net new, the deal cycle alone might take a minimum of three months, probably six months. And if you are literally starting from scratch, you need a certain number of months to start generating pipeline in the first place.<\/p>\n
Having a dedicated ABM manager or agency, someone who doesn’t distract from all the existing marketing and sales activity, is really important. Otherwise enterprise can easily suck up your entire organisation’s resources, and you don’t get the results for quite a long time. What can then happen is everything else stalls whilst you’re trying to go to market, and that can be an absolute disaster.<\/p>\n
Often founders try to stretch their existing AEs to go from mid-market to enterprise. The sophistication of the buyer on the other side, the complexity of managing multiple stakeholders, and the rigour and patience needed to run through all the blockers and the myriad challenges are often not a good fit for your existing AEs. Finding someone with that experience to lead the enterprise charge is often a very, very good investment.<\/p>\n
From what I saw at RevvedUp, a lot of ABM programmes stalled before they’d really begun because sales and marketing couldn’t get on the same page. Teams weren’t having internal alignment discussions before kicking off their ABM programmes, even to the point that they couldn’t agree which accounts should be prioritised or become target accounts. Not agreeing what success metrics look like was another common one.<\/p>\n
With expectations and resourcing sorted, you need to decide who you’re actually going after. Your enterprise ICP won’t look like your mid-market one.<\/p>\n
Founders sometimes go too ambitious and try to target huge, huge enterprise companies. There’s a very big difference between landing a deal with a thousand-person company, which for many startups would be enterprise, and landing a deal with a 10,000 or 100,000 person enterprise. They have completely different systems requirements, procurement processes, legal and so on.<\/p>\n
Going too greedy, with your eyes too big for your belly, and going after the biggest enterprise in your market is not always the smartest thing. What you want to do is ladder up. Go as close as you can to the existing social proof you have, whilst still punching above your weight and trying to break into bigger and bigger accounts. A more gradual move into enterprise works better than trying to leapfrog several rungs up the ladder, and trying to go after too many accounts in one go, so it doesn’t really become ABM, is another mistake I’ve seen.<\/p>\n
Trying to go after too many accounts in one go, so it doesn’t really become ABM, is another mistake I’ve seen.<\/p>\n
This is the core of the work. The changes fall into three areas: how you run discovery, how you market, and how you manage deals.<\/p>\n
Startups probably don’t do enough discovery. With a 10k or 20k deal, a really strong one-hour discovery session with one or two of the key stakeholders might generally be enough to get the deal over the line, or certainly set it in the right direction. With enterprise, you probably need multiple discovery sessions (way more than you think…and it shouldn’t stop until the ink is dry on the contract)! You need to do far more customisation of the product experience and the demo experience during the sales process too. Often you need to bring in solutions engineers or similar. Just pitching a set solution often falls flat.<\/p>\n
On the marketing side, the single highest-leverage change a startup can make when moving upmarket is getting really good at field marketing. I think it’s underestimated just how impactful field marketing is to the whole enterprise motion. That includes industry trade shows, exhibitions and conferences, and also running your own private events, whether that’s days out to sporting events and corporate hospitality, or VIP dinners and breakfast meetings. A lot of good enterprise marketing hangs off good field marketing.<\/p>\n
There’s a whole myriad of other marketing changes alongside it:<\/p>\n
\u2192 Product marketing needs to get sharper, and it’s more complex for enterprise.<\/p>\n
\u2192 Nurture marketing is critical, so always having something valuable, useful and relevant to say, particularly during those long nurture cycles and deal cycles, is really, really important.<\/p>\n
\u2192 Super credible thought leadership and content marketing is vital to any enterprise marketing motion, and so is AEO, GEO and SEO, particularly in today’s market, because decision makers and stakeholders are going to go to ChatGPT or Claude and search specifically for how your solution will work for them. You need all the content coverage that answers their questions better than your competitors do.<\/p>\n
On the sales side, having real rigour around the deal management process is probably the highest-leverage thing you can do. That means being religious about MEDDPICC and using it to help the reps navigate the deal, making sure it’s not just a box-ticking exercise but actually becomes an active guide to where there are risks and weaknesses within the deal. Then having a plan for overcoming those, and uncovering unknowns and assumptions, becomes probably the biggest weapon you have within the sales team for starting to win enterprise.<\/p>\n
Only once the motion is rebuilt does AI start paying back. There are lots of great places where it can help with enterprise marketing and sales, and they map straight onto the motion above.<\/p>\n
The obvious, fairly well-worn areas are deep account research and buying committee mapping. This is exactly where that potential client with ten weeks of manual research went wrong. Not thinking smartly about where you can apply AI, and relying on the old way to do things AI can do uniquely well, is definitely a mistake.<\/p>\n
Signal identification means tracking all of your target accounts and looking for any changes in circumstances: leadership changes, promotions, people leaving, switches in public sentiment, earnings calls, reports and financial filings, new partnerships, new initiatives, new funding. There’s so much richness out there, and it’s really important that you’re not second to that information.<\/p>\n
Going beyond simple signals, AI can synthesise lots of different signals, from your target account lists, competitors and the wider industry, to help you form a unique point of view on what your right to win these accounts is, and how you’re in a unique position to help them. Going beyond a singular signal or trigger is really important, and that’s where AI earns its place.<\/p>\n
But the only way it will do a good job is if it has all the unique context and organisational information that feeds your overall motion. Otherwise, it will give you generic outputs. Giving it bespoke and unique inputs is the only way you’re going to find alpha with AI, much like anything.<\/p>\n
You can use AI to take big content assets, like industry reports, webinars and event reports, and tailor them in a really specific and meaningful way to each account on your target list, and each stakeholder within that account. A few years ago that might have taken a whole content team multiple weeks, and therefore often didn’t get done at all, or only for one or two of the most important accounts. Now you can do it for all of them.<\/p>\n
It’s super important that you have the rigour and guardrails in place to make sure it doesn’t descend into AI slop. Done right, it can be incredibly powerful.<\/p>\n
I think an underutilised way of using AI in enterprise is coaching and brainstorming with reps.<\/p>\n
Getting it to run through a call transcript and codify which parts align to MEDDPICC is in some ways a bad use of AI, because it takes away the analytical, rigorous thinking the rep needs to do to navigate the deal. Where you do apply it to MEDDPICC is having it unpick what was said, challenge assumptions, and look for weaknesses and missing information, so it can proactively coach a rep through potential issues with the deal and bring ideas for how to overcome them.<\/p>\n
Suggesting useful, interesting and timely content that reps can share with their stakeholders, so they stay top of mind and show value throughout the deal cycle, is another really nice use case.<\/p>\n
AI can also be used really productively in field marketing: understanding who’s going to an event, creating bespoke event briefs to share with everyone attending from your side, suggesting who to prioritise meeting, and making the post-event follow-up more personalised and relevant, but faster to do.<\/p>\n
Those are just some of the specific areas where I’ve seen AI work very well, and every one of them depends on the motion underneath being built for enterprise first.<\/p>\n
If you’ve just raised, or you’ve redone your plan and the numbers only work with enterprise in them, it’s tempting to point AI at a target list and hope the pipeline follows. But going upmarket is a motion problem first, and AI can only improve the implementation once the right structures are in place.<\/p>\n
That means laddering up from the social proof you’ve already got, rebuilding discovery, field marketing and deal rigour for a much bigger and slower-moving buying committee, and only then layering AI in where it does things uniquely well. It also means being realistic that closed-won deals are probably at least 6 months away, and putting dedicated resource behind it so enterprise doesn’t suck up everything else while you wait.<\/p>\n
Get that right, and the 10 weeks of hand-research that made one programme look unviable becomes something you can do properly across your whole target list, for every stakeholder in every account.<\/p>\n
That’s what we do at AI GTM Studio. We design your enterprise marketing programme with you, from ICP and target account selection through to field marketing, nurture and deal rigour, and then we run it, with AI built in where it earns its keep and your team in the driving seat on the relationships. It’s also the dedicated resource most founders don’t put behind enterprise, without pulling your existing team off the pipeline that’s already working.<\/p>\n
If you’re about to make the move upmarket, or you’ve started and it’s stalled, get in touch with AI GTM Studio and let’s talk about designing and running your enterprise marketing programme.<\/p>\n","protected":false},"excerpt":{"rendered":"
At some point, almost every B2B business – AI, SaaS, even good old fashioned services – will make a decision to ‘go upmarket’ and try to start winning enterprise clients. I’ve seen enterprise done wrong plenty of times, both when consulting with clients and seeing what they were doing previously, but probably the most exposure […]<\/p>\n","protected":false},"author":1,"featured_media":170,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-171","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-uncategorised"],"yoast_head":"\n