Selling to enterprises is completely different to targeting SMEs and I’ve seen countless startups try to move upmarket by using the same sales playbook that worked for smaller deals. And it never works. 

The simple fact is that enterprise selling requires a fundamental shift in strategy, process, and mindset. 

The enterprise difference 

Let me first point out what makes enterprise sales different. For starters, you’re looking at much longer sales processes. We’re talking six to 18 months versus the under-six-month cycles you might be used to with smaller companies. 

You’re also no longer selling to a single decision-maker. In enterprise deals, you’ll typically engage with five to ten different stakeholders within one organisation. This multiplies the complexity massively. 

The upside thought is that deal sizes are much bigger. These opportunities typically start at £50k+ ARR, which can transform your business overnight. But with that comes formal procurement and legal processes that smaller companies don’t usually have. And the product and feature requests will be more comprehensive as these are professional buying teams with experienced subject matter expert teams who know exactly what they want. 

Not all products are ready for enterprise though. Security requirements alone can be a massive hurdle. Always make sure your product infrastructure is enterprise-ready before you begin to start selling enterprise deals.  

When to target enterprise deals 

It’s sometimes okay to not sell to enterprises. Some companies exclusively serve enterprise clients, while others will never go upmarket. And both approaches can work. 

Don’t chase the £50k deals just because they seem more exciting than your current £5k ACV. It might actually be better for your business to sell ten £5k deals than to pursue a single £50k opportunity. 

The best way to determine if you’re ready?  

Set up what I call “friendly conversations” – these are interview-type sessions with the types of companies you’d like to work with. If you’re currently selling to mid-market and wondering about enterprise potential, schedule 30 calls with enterprise companies. Don’t sell to them; simply say, “I’ve built this product, I’m the founder, and I’d love to get your perspective.” 

This approach allows you to sense-check whether your product will land well in larger organisations. Is the problem you’re solving significant enough in an enterprise context? Or will you hear, “We’ve already got a team that handles that”? 

If after speaking with 30 potential enterprise clients, the consistent feedback is “our business would love something like yours,” then you’re probably onto something worth pursuing. But be warned, trying to satisfy an enterprise market might lead you to burn cash and resources quickly, and you might end up building a confusing product if you try to serve both SME and enterprise simultaneously. Being laser-focused is almost always the best approach. 

Transforming your GTM motion for enterprise 

If you do decide to pursue enterprise clients, your approach needs to be completely different. You need to rethink your entire go-to-market motion. 

Consider how you might leverage partners.  

Rethink your marketing strategy for these larger companies – their expectations differ substantially from smaller clients. Forget automation; enterprise sales requires a completely personalised, manual, high-touch approach. 

Account-based marketing (ABM) might now be essential when it wasn’t before.  

Ask yourself: where do these people hang out? They’re in different places than your current audience. Map out a new GTM motion specifically for these types of companies, recognising that their buying process is more sophisticated. You need to level up your entire approach to align with their expectations. 

A critical aspect of this shift is addressing multiple stakeholders. Your marketing, website, and outreach need to speak effectively to 5-10 different people within one business: 

• How will you communicate with the economic buyer – the person who holds the budget and will sign the contract? 
• What’s your message for decision-makers? 
• How will you engage end users—the people logging into your software daily – and get them excited? 
• How will you reassure legal teams and ensure your contracts are enterprise-ready? 

These considerations must be addressed before you start actively selling. 

Discovery: Where enterprise deals are won or lost 

The biggest transition when moving to enterprise sales is understanding that you’ll fundamentally win or lose deals during discovery.  

As a small company selling to a big company, you’re at risk of having your time wasted. They can kick tires all day, pull you around for months, and ultimately burn countless hours of your time. 

Being excellent at discovery is your protection against this. You need to thoroughly understand: 

• If and how you’re adding value 
• Their specific pain points 
• Their procurement process 
• Their IT evaluation process 
• Their decision-making framework 

Big companies have professional buying processes, and you need to run a professional sales process that aligns with theirs.  

A common mistake is getting excited after a first meeting, doing a demo, and then sending a proposal while the prospect is still in “evaluation stage one” of their multi-stage buying journey. This misalignment can kill deals. 

Getting really bloody good at discovery will change your life with enterprise opportunities. It allows you to qualify and disqualify early, establish credibility, and engage as a peer. Running a slick sales process elevates your product and company in their eyes. Otherwise, you risk looking like an early-stage company that’s “too risky” or might “run out of money,” prompting them to choose the more established, expensive vendor. 

Sales strategies for enterprise success 

In my experience, there are several specific differences when it comes to targeting larger deals. And founders need to make sure they make them part of their enterprise sales process: 

• Tailored demos – Make demos engaging and tailor them for different audiences (end-user demos vs. decision-maker demos that focus on visibility and time/cost savings) 
• ROI-based proposals – You need comprehensive, ROI-based proposals rather than simply quoting a price 
• Objection handling to experienced buyers – Develop strong objection handling and negotiation skills to deal with experienced buyers 

For example, don’t just say “here’s the £50k price.” Instead, leverage your discovery findings: “We learned you’re currently wasting time on X, which costs you £250k annually. For £50k, you’re saving £200k per year.”  

Make your proposals value-driven rather than merely presenting a price. 

Mistakes you need to avoid 

The biggest mistakes I see founders make when making the transition to enterprise sales are: 

1. Scrappy sales process – Running a scrappy sales process that makes your product look inferior and raises red flags 
2. Insufficient discovery – Conducting insufficient discovery, which leads to getting ghosted or passed around endlessly 
3. Not selling value – Selling a product instead of selling pain resolution 

With smaller £5k deals, clients might be buying a product: “Click here, it does that, it’ll make your life easier.” But with £50k+ opportunities, prospects are buying solutions to pain points, focusing on ROI and transformation. Not recognising this difference is a fatal error many founders make. 

The impact of getting it right 

When you successfully transition to enterprise sales, it changes everything. You’re selling to massive companies and bringing in substantial ARR. 

I recently spoke with two founders who literally haven’t needed another funding round because they’re now closing enterprise deals. One pivoted from selling unsustainable £1k deals to SMEs and is now consistently landing £100k contracts. Five or six of these deals represent £500-600k in ARR—which for many startups is equivalent to a pre-seed investment round. 

The impact is immediate and powerful.  

Enterprise clients often pay upfront, so signing a £100k deal means getting that cash into your business the following month. This accelerates growth, potentially eliminates the need for external funding, and dramatically increases your valuation. For a high-growth SaaS company, every £100k of ARR you add through these large deals potentially adds £1 million to your company’s valuation. 

But getting it right requires a different mindset, process, and skill set.  

The key is determining if your product truly solves a significant problem for enterprise clients, developing a tailored go-to-market strategy, excelling at discovery, and building the specific sales capabilities needed to close larger deals. Get these elements right, and you’ll unlock a level of growth and profitability that can change the entire future of your business. 

Author: Matthew Codd

I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.  

I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.  

I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.