10 Sep, 2026
Enterprise Sales Strategy: 8 Things to Change Before You Chase Bigger Clients
Every business that decides to go upmarket tries the same thing first. Turn the ads on, loosen the filters on the outbound list, and point the same offer at bigger companies.
We tried exactly that at Rocket SaaS and it flopped. An enterprise sales strategy is not a targeting exercise. Bigger buyers decide whether you are for them long before anyone picks up the phone, and most of what they judge sits on your website: how it looks, how it is priced, and who the messaging is written for.
This article walks through the eight changes we made over the past year to move upmarket, in the order we made them.
On episode 110 of SaaS Marketing Weekly, our founder Ryan James walks through all eight.
Listen to Episode 110: 8 key things you must change to sign bigger clients
The eight changes at a glance
- Research what bigger buyers want
- Revisit your pricing before anything else
- Refresh the brand
- Rewrite the messaging without losing your smaller clients
- Lead with a free audit
- Build an ABM strategy
- Build referral partnerships and find your door opener
- Tell everyone you are going upmarket
What is enterprise sales?
Enterprise sales is the process of selling to large organisations, where more than one person signs off the purchase and procurement gets involved. The enterprise sales cycle runs for months rather than days, and the buyer usually has a supplier or an in-house team already handling the problem you solve.
The enterprise sales definition varies by industry, so the enterprise sales meaning you work to depends on who you already sell to. What counts as an enterprise customer in one sector is a mid-market account in another. Ours is companies between 50 and 500 people, which is enterprise relative to the clients we started with.
You are rarely the first option on the table. You are the option trying to displace whatever is already there, which is a different sell from convincing someone who has never bought anything like your product before.
Why widening your targeting does not work
We assumed going upmarket was a targeting exercise, so we turned the ads on, widened the filters on the outbound list, and pointed the same offer at bigger companies.
It does not work that way. A buyer that size lands on a website built for companies half their size, decides you are not for them, and closes the tab. Extra ad spend does not fix a first impression that has already gone wrong.
Selling to enterprise customers means being judged on the same signals every larger business uses to assess a supplier: the website, the case studies, the pricing page. B2B enterprise sales turns on those signals long before a call happens.
Bigger buyers need to trust you before they buy what you are selling. Everything in the rest of the enterprise sales process is about earning that trust in advance, on the page, before anyone from your team says a word.
1. Research what bigger buyers want
If you already have clients at that size, start with them, because the relationship exists. Interview them, take them to lunch, and ask what changed as they grew. What do they now handle in-house, and which problems appeared that they never had when they were smaller?
Be direct about why you are asking. Tell them you want to sign more clients like them, and ask what companies their size care about. Most people are happy to answer, and the responses tend to be blunt.
If you have no clients that size yet, use a tool like Wynter to survey the upmarket buyers you want to reach.
Here is our biggest finding from doing the exercise ourselves:
What larger companies wanted from a marketing agency turned out to be the opposite of what smaller ones wanted.
That is the moment your research turns into a messaging and content plan for winning bigger clients.
The questions to ask
- What do you care about?
- What problems are you trying to solve right now?
- What resources do you have in-house?
- What budget would you put against this problem?
- Which features and benefits matter most to you in a platform?
2. Revisit your pricing before anything else
Everybody checks your pricing page to work out whether you sell to companies their size. Low pricing tells a larger buyer you play in a smaller space, so they leave without contacting you.
Ryan has been asked outright on calls: “Why are you so cheap?” We lost those deals.
The fix is an enterprise tier on the pricing page. A sliding scale by user count, tiered pricing by requirement, or whatever suits your SaaS enterprise pricing, as long as the page does not rule you out on sight.
You can see how we handle it on our pricing page, and we break down the wider approach in how leading SaaS brands structure their pricing.
3. Refresh the brand
Larger buyers judge your credibility on the look of the site before they have read a word. A dated design, or cartoons bouncing around the homepage, counts against you before you get the chance to explain what you do.
Plenty of enterprise deals are won on relationships and account-based work, so the website is not always the deciding factor. More often than not, though, you need a slicker presence to be taken seriously by a buying committee that has never heard of you.
The fix might be a full redesign, or it might be a conversion exercise on the site you already have. If it is the second one, that is what our website conversion rate optimisation service is for.
4. Rewrite the messaging without losing your smaller clients
The research you do at the start pays off here. Messaging that lands with a smaller company usually falls flat with a bigger one, because the offer underneath it is different, even when the product is not.
What changes between the two audiences
To a smaller company we say we become your marketing department, and we build everything from scratch because there is nothing in place yet.
To a bigger company we say your in-house team already has strong operators, and what is missing is a demand generation strategy and LinkedIn ads expertise at a senior level.
To a company with one or two marketers, becoming their marketing department is the whole pitch. To a company that already has a marketing team in place, that line means nothing. They do not need a department, so the message has to change entirely.
Then comes the harder problem. Most businesses going upmarket want to keep both audiences at once, and changing your homepage to talk exclusively about enterprise costs you the smaller clients you still want.
The two-box homepage
Our fix is running on rocket-saas.io right now. Two boxes on the homepage, one for startups and one for growth-stage companies, each linking through to its own page written in the right language for that reader. Campaign traffic then lands on the matching page instead of the homepage, so nobody has to read past the parts that were never written for them.
You can see it live: startups and growth-stage.
5. Lead with a free audit
Most large brands already have a supplier or an in-house team, so an offer to sell them a platform gets the same answer every time.
“We have one, we are already doing this, it is not a priority right now.”
An audit turns that around, because you tell them what is going wrong before you tell them what you sell.
Name the problems they are probably still carrying. Name where their budget and their time are going right now. Offer to audit the process with no obligation to work together afterwards. Cap the number of places so the offer reads as considered rather than open to anyone, and hand over something written at the end that they can act on whatever they decide about you.
It works because bigger buyers arrive sceptical. They have been burned by suppliers before, so you have to prove your worth before you get anywhere near the door. An audit costs you time rather than money, and it is the one offer in this whole enterprise sales strategy that a sceptical buyer has little reason to turn down.
Our own free website review runs exactly this play, capped at five places a month.
6. Build an ABM strategy
Going deep on ABM is a whole separate piece, so here is the short version. Hand-pick around a hundred accounts you want, and work them with intent rather than volume.
A few plays worth running:
- Invite the account onto your podcast instead of pitching them
- Get your founder connecting with their founder on LinkedIn
- Co-host webinars and events together
- Run direct mail
- Put hyper-targeted ads in front of a pain point you already know they have
- Turn up at the events they attend
Read the full plan in our guide to using ABM to land big clients.
7. Build referral partnerships and find your door opener
Big deals rarely start with a LinkedIn ad and a form fill. They start with somebody who is already in the room, whether that is an ex-colleague who moved to that company, a supplier you already work with, or an existing client who knows people at your target account.
Work through the people you already know, offer a referral fee for anything that closes, and get the initiative on their radar properly rather than mentioning it once and hoping it lands.
Partnering with consultants and advisors
Well-known consultants and advisors in your space already have the trust you are trying to build. They carry an audience, and most of them have no platform of their own to deliver the work through.
That gap is the opportunity. Package your services together, run events, webinars, podcasts and newsletters jointly, and pay them a share of the monthly revenue for as long as the client stays.
Then use the partnership itself as the pitch. We work with this named advisor, and this is what we deliver together is a stronger opener than anything either of you could say alone.
8. Tell everyone you are going upmarket
Ryan calls this his favourite piece of advice, and it costs nothing. Tell the whole team the initiative is live, and be specific about it: the revenue band, the headcount, and the type of company you are trying to sign. Ours was companies between 50 and 500 people.
From there, everybody answers the how is business going question the same way: we are trying to sign larger clients, these are the ones we want, do you know anyone?
Ryan made an offhand comment over lunch that led to an invitation into a networking group for owners of tech companies above a set revenue. He joined, has lunch with the group monthly, and wins business from it on a regular basis. The same question, sent as a single LinkedIn message, works just as well.
Start this week
This work took Rocket SaaS about a year, start to finish.
Most of it, though, is one-off. The pricing page, the brand and the messaging split get built once and then keep working in the background, while the partnerships and the ABM plays run alongside them for as long as you keep at it.
Start with whichever is quickest and costs you the least. Fix your pricing page, or ask three people for advice on going upmarket and see where the conversation leads. Either one will tell you more about what is holding your enterprise sales strategy back than another month of outreach will.
Listen to the full episode on SaaS Marketing Weekly, or take a look at our demand generation strategy service if you would rather build this with us.
Frequently asked questions
A software company selling a platform licence to a business of several hundred staff is enterprise sales. More than one decision maker signs it off, procurement gets involved, the cycle runs for months rather than days, and the buyer usually has an in-house team already working on the problem.
Rocket SaaS set out to sign clients with a headcount of 50 to 500, and getting there changed what we sell rather than who we email.
It is slower rather than harder. Larger buyers have been sold to before, so they arrive sceptical and want proof before they commit. Rocket SaaS spent about a year changing its pricing, brand, messaging and offer before it signed these clients consistently.
The work is front-loaded into positioning rather than into the sales conversation itself, which is why the eight changes in this article come before any outreach.
Commercial sales cover mid-sized businesses, where one or two people can approve a purchase. Enterprise sales cover large organisations with several stakeholders, a procurement process, and an in-house team already handling the problem you solve. Messaging that wins one rarely wins the other.
That is the reason behind splitting a homepage by company size rather than writing one page that tries to speak to both.
Lead with a problem they still have rather than a product they have already bought. A free audit works because most large brands run a supplier or an in-house team already, so an offer to find what is going wrong gets further than an offer to replace what they have.
Our guide on how to find and win corporate deals covers getting the introduction in the first place.
Enterprise clients are large organisations that buy through a committee rather than an individual. What counts as enterprise depends entirely on who you already sell to. Pick your own definition, write it down as a revenue band and a headcount, and make sure the whole team knows what it is.
Plan for about a year. Rocket SaaS set the target roughly twelve months before the deals became consistent. The pricing page and the messaging split are the quickest two things to change, so start there if you want to see movement fast.
Get free ✨ SaaS marketing strategies and campaign ideas in your inbox every Thursday
Free SaaS marketing strategies & campaign ideas in your inbox every Thursday
Receive actionable SaaS marketing ideas to implement in your business
