Last updated on July 6th, 2023

Enterprise SaaS Pricing Advice we Wish we had Known

Pardeep Kullar
Pardeep Kullar
Enterprise SaaS Pricing Advice we Wish we had Known

We found SaaS enterprise pricing to be confusing at first but having been through the process many times now, below is our advice for our younger selves. We cover 4 different enterprise deals for Upscope co-browsing and how each turned out.

Related: How we Thought we'd get Enterprise Buyers and what Really Happened

Important read: Why Serial Entrepreneurs do Go-to-Market Strategies first

Also see: 10 Companies give you their Best Advice for Doing Demos that Sell

What's an enterprise customer?

Any large company paying $1,000+ per month is enterprise for Upscope.

Upscope is a co-browsing solution. They're typically looking to buy our product for their customer success, account and support teams or to use our API to completely white label our solution for their own internal needs or as part of a product they sell to their customers.

Enterprise 1: Large company purchasing 100s of licenses

This is the most common type of enterprise deal.

They are veterans at buying SaaS, they expect volume discounts because of the number of licenses they intend to buy. They want to use Upscope as a sales tool for their sales agents.

We already have a table of discounts we apply depending on volume of licenses purchased and the length of the contract.

We charge them less than the standard business pricing per seat because they are buying 300+ licenses. We also offer the additional discounts if they commit to a 3 year contract vs a 1 year contract. A 3 year contract gets them a further 30% discount.

This is the typical enterprise deal for us. Below you'll see others and why they might be different.

Enterprise 2: Mid-sized company

They want to build Upscope into their own support tool so their staff can instantly screen share with customers.

They'll need to use our Co-Browsing API for the integration, which is only available with the enterprise plan and normally for higher volumes.

What should we charge them?

Charge them the standard business plan fee + an extra $10 per agent.

This is a little unusual for us

If you looked at most of our enterprise deals then rarely do we charge them extra. In fact we have volume discounts.

However this company is not purchasing a large volume but want to use the Enterprise level API.

Why charge them this rate?

They are not purchasing a large volume but need our API which sits on the enterprise plan which is normally for large volumes.

They're going to need an individual service level agreement and a whole raft of additional docs signed up.

They have lots of additional processes and procedures around data security.

They're going to require a lot of support while they integrate it and get going.

They care about the pricing but don't mind paying extra as long as they feel it's for the right reasons as they wish to not only get a higher level of support over time but may need additional customisations, so be up front about it.

Lessons learned

The size of the company may not correlate with the amount of support time they require. Sometimes the larger companies pay the money, integrate it and off they go. The smaller ones might take 2X or 3X the time.

Enterprise 3: Billion dollar established company

They want to purchase our standard business plan for a large number of internal support and account management staff.

What should we charge them?

Our standard business plan pricing. They fall below our larger volume discounts but they never even asked for a discount or even appear to care about it. Also, they want to pay monthly. They can certainly afford it but for whatever reason they prefer monthly payments.


It works for them.

They want to trial it for a long time and see the ROI. After that, they just want the standard pricing until they decide otherwise.

Their primary concern is solving their own problem.

The value we provide is far greater than our per seat pricing so they are not concerned with the price.

I'm also hearing that some 20% of larger enterprise customers of SaaS companies are paying monthly when in the past they paid annually by default. These guys are happy paying monthly and they've been customers for years now.

Lesson learned

Some deals are simple, so let them be simple by being patient.

They didn't care about the price, our pricing was a tiny blip on their budget and because our software would truly help solve their problem they had enough urgency to get it done and know the ROI was going to be great.

Good fast responses matter because they probably contacted a number of other co-browsing companies and we were instant in our replies.

That may have been the primary reason they went with us. We've overheard accidentally recorded answering machine messages and accidentally cc'd emails where clients discussed picking us for our speed of reply. This has happened twice, once via phone and once via an accidentally cc'd message.

They care about about data security because they have a department that cares about data security so the people who first signed up need to pass on the key data security related information to that department. Have the security docs and answers listed on the home page and in help files and maybe in a pdf too.

I wish all deals were this simple.

Enterprise 4: Usage based pricing for white label fast growing SaaS company

They want to completely white label our product as part of their product which they're selling to other large organisations.

What should we charge them?

The per seat pricing does not work for them because they don't know how many people will need it month to month.

This company and many like it NEED hourly or transactional pricing because they might be pricing to their clients per hour or per event (every time they use it) rather than per seat.

Do usage based pricing.

Instead of charging per seat, charge per hour their customer's support agents use it but have a minimum number of hours per month you'll charge by default.

Also, get 6 months of payments in advance.


Talk to them, understand their situation and their potential ROI from using Upscope and remember that they'll need extensive support in the early stages.

They don't know how much their customer's support agents need Upscope yet but it'll minimally be X hours per month given our previous average usage figures for that industry. Figure out X with them and charge for it.

They are quite used to paying annually for software though in this case they need to re-assess every 6 months so charge them 6 months in advance rather than annually.

Lessons learned

Companies like this need to know that our product will still work for them even if something happens to our company. On-premise licensed software which they can independently run if something were to happen to Upscope matters to them. Also, their clients are finance companies and they need complete control over the data for some of them.

Lessons learned from enterprise deals 4, 5, 6...

  1. As tech co-founders we buy software entirely differently to enterprises. We sign up, buy, use and maybe ask questions after if we run into a problem, maybe. For larger enterprise deals the buyers expect you to demo them, follow up, provide docs, offer services and more. It's best to imagine someone sitting in a grey cubicle in an office looking forward to your demo and your follow up because they enjoy that. Not sure how often it's true but it's a good mindset.
  2. Each deal is different and it makes sense to show flexibility on pricing, they really appreciate that. It can be per seat but it can be usage based, event based and it can be priced per physical seat (for companies that have several shifts of workers).
  3. They expect volume discounts if they're buying at volume. We have ready to go pdfs which show them volume pricing with discounts. We have one pdf for each major currency we most commonly work with: US dollars, Euros, Pounds. There are also further discounts depending on the length of the contract.
  4. Departments have budgets and apparently prefer to know what the total cost is so they can see if it fits in their budget. I had not considered this very obvious fact. The figure that sounds big to me might just be a "pfft" for them so no need to be shy about it.
  5. They might want help with onboarding, training, implementation and more. Some companies expect you to charge for this as an additional services fee. We have not done this so far but it has come up. So far we've only charged for extra custom development work.
  6. Hire a sales exec. Get someone with sales experience within your industry who you would buy from. They speak an entirely different language sometimes and they are DIRECT with questions to customers about pricing, budget, next steps in a way in which you most likely won't be. I'm still in shock from hearing our first sales exec hire talking to a customer - the instant rapport they find by speaking the customers language and getting down to business and how brutally direct some questions are. The advice we heard via Jason Lemkin (SaaStr) is that the simplest way to figure out if someone is a good potential sales hire is to ask yourself "would you buy from this guy?".
  7. THEIR requirements are very specific to their jobs. If you're a co-founder you're great at passionately talking about your mission, vision and future of your product as well as the immediate practical problem you solve for customers. The person in the large enterprise you are talking to may find some of that inspiring but their mind is on their job, target, boss, department and to understand that you have to listen. I'm saying this because I've made this mistake. I even thought a call went great but I had not LISTENED to their priority requirements. Felt like a dumbass when they didn't pick us.
  8. Security is a big issue and you can lose a deal if you don't take it seriously. A buyer told us that another company did not take their security form seriously so they dropped them (and that deal brings us 100k per year). This is before they sent us that security form. In other words they were saying "Take this seriously". We were fortunate that we got ISO certified quite early on even when we only had 3 people in the company and that helps us fill out those forms**. Some of them are 60 pages long and take a full day to fill out.** It's part of the cost of doing business. If you're not ISO certified or SOC2 certified and still want to be able to fill in those forms correctly then read this.

Perpetual license deals with annual fees

I'm adding this here because when one partner first mentioned "perpetual licenses" it confused the hell out of me.

If they mention perpetual license deals then they're operating in a different way to your normal per seat pricing. We come across this licensing model when we're talking with companies that want to partner with us and integrate our systems into theirs to sell to their large clients.

The partner might want to buy 1,000s of seats to sell to their clients. This leaves you imagining 10,000s of dollars per month in revenue but you can't force your pricing on their perpetual license business model they already work with.

They might be charging their clients a one-off perpetual fee per seat e.g. $800 one time forever and then they charge an annual maintenance fee per seat e.g. $240. The annual maintenance fee is the recurring revenue.

They might add your service on as an additional $300 one off fee and $30 annual maintenance charge service. We're still learning about these models so this is just an example but this roughly how it works.

Read more about perpetual licenses, OEM deals and SaaS further down in this post.

What questions do enterprises ask us? They'll look for trust and experience.

Where are you based? How many people in your company? They're wondering if we're for real and can be trusted. They don't want to buy a product from lunatics running a scam. That about us page matters. That Linkedin profile matters.

Who else have you sold to before? Any big companies? Many want to see PROOF that your product works and the best way is to see if another company in their industry uses it. Social proof is still king. Of course, if you have not sold to anyone you can only show them other well known companies you have sold to or seemingly trust worthy organisations at the very least. Everyone at some point got that first big one.

Some of the business development guys ask if we've sold our product to large companies before because they're evaluating us as an acquisition as much as a service to integrate or partner with. Damn odd experience the first time round. It's a very long term process with these guys.

Are you funded? They're asking if Upscope is about to go down any time because of a lack of money and the right response is to tell them that this is not our first startup and we're self-funded, profitable and stable. If they're looking to do an on-premise integration then tell them it will continue to function even if Upscope did somehow die.

Can you do a POC (Proof of Concept)? Imagine you're on a demo call with a potential big buyer and they say they want to 'Do a proof of concept' and you just say 'yes, I am sure that is possible' when in fact you don't know what a proof of concept is. They're talking about a trial.

This is basically the company saying they don't really know how many people are going to use your product and they need to test it out. This could be an extended trial period or some other way of proving the product. You might charge for this extra trial period or you might not. You could even charge for it and then deduct it from the annual payment they'll make after. Read more about POC here.

Why are these companies interested in Upscope?

Upscope is no-download interactive screen sharing for onboarding and support that is likely to be a default form of screen sharing in the future.

You can send your mouse cursor across the internet to appear on your customer's screen to scroll, click and type for them.

It's used by live chat support agents, contact center agents, customer success and sales teams.

Take a look at Upscope co-browsing here and also check out some of our docs we've added to the site because many are there for enterprises.

Pardeep Kullar
Pardeep Kullar

Pardeep overlooks growth at Upscope and loves writing about SaaS companies, customer success and customer experience.