/ SaaS

What’s the Process for Selling SaaS to Enterprise?

Ever wonder if those boring whitepapers and security pages on some SaaS websites are necessary? Do you have to email people to gain enterprise customers? Below we describe what we hoped enterprise sales would be like, how we realistically thought it would be and what it turned out to be with Upscope.

Related: How We Priced 3 Enterprise Software Deals

Related: Why SaaS Companies Realise they Need Enterprise Sales

Also see: Upscope's Pricing Model that Worked

What we hoped the process for selling to enterprise was


  1. Person from big company sees our content and signs up.
  2. They install the software and trial it.
  3. They pay big bucks for it.

If I could insert a laughing emoji that gifs into a crying emoji here, I would.

What we realistically thought it would require


  1. Our enterprise sales sniper sends smart customised emails to person in big company.
  2. Person in big company talks to their team and convinces them to try the product.
  3. They trial the software.
  4. They pay big bucks for it.

The customised email part certainly works for companies but we don’t have enterprise sales snipers at present, we’ve gone a different route of mostly inbound marketing and some more general emails.

What it turned out to be


  1. Person or buyer team at big company comes to our site from content or an integration listing, a comparison site or even a cold email we had sent out (but it's hard to track sometimes). They check out the site and ask questions via live chat or email about security and data without signing up. Then they go away.
  2. Person returns to ask more questions about security, contracts, pricing and goes off to thoroughly evaluate the product compared to competitors.
  3. They talk to their team, they pass round those whitepapers if you have them, they get clearance from their development or security team on the product. Often the key questions focus on data because they don’t want to get fired for screwing up with customer data.
  4. They ask us to give a demo to a few key knowledgeable people.
  5. They ask for a second demo to key decision makers in their company.
  6. Person at big company eventually, sometimes after a month or 2, signs up for trial and it goes through testing on their local machines.
  7. Person at big company asks for an extended trial because 2 weeks is not enough to do internal testing, testing on staging server and then testing on production server.
  8. Person at big company might need to prove the value of product via statistics to themselves and others in the company so they’ll ask you for some way to monitor stats during the trial.
  9. They finally pay big bucks for it.

Other things they bring up and what to do

Upscope is a co-browsing (aka no-download interactive screen sharing) service and we get all sorts of requests including on-premise deployment, purchase orders, security questionnaires, EU servers.

Purchase orders

Most of your smaller customers plug in their credit card and they’re off but some big companies don’t do that.

They might send you a purchase order.

Yeah, wtf is that right?

You’ve built an entire system of automated accounting on Stripe + Xero and then suddenly people want to send purchase orders that require manual entry.

Security questionnaires

They might need you to fill in a security questionnaire which is 8 pages long.

We have a separate security page which details all our security initiatives but they will STILL send us this questionnaire and it really is 8 pages long and asks lots of questions.

Just get through it as best as you can.

Oh and some people will have a 3rd party vet you for security. So, you have to fill in their questionnaire and they go off and do all their checks to clear you.

On-premise deployment

They might ask for on-premise deployment which then requires a different tech process and complexities in maintaining it.

This happens with certain financial organisations that need complete control over what goes in and out. We do on-premise deployment and people are willing to pay for it but we don't do it for your 2 person SaaS company, it's done for larger organisations, paying annually and with additional charges for consultation beyond the normal process.

Regional servers

They might need data to only pass through servers in their country so you’ll have to add some to their region.

What can you prepare so you get these enterprise deals?

Have live chat, have a phone number listed even if they don’t use it, have an about us page that says you’re not high and about to smoke their customer data in a pipe, have your location listed and have some of those more boring security pages, white papers and videos.

Alternatively, choose life and take up fishing.

"OEM" deals are also completely different

Some old school companies still think in terms of OEM and vendor.

They operate in a slightly different way to other new fast growing startups.

OEM deals are when a big company integrates your product into their core product and then pays you for every customer who uses it but it’s branded under their name.

This is normally called whitelabelling but if they use the term "OEM" then you might be in for a different kind of ride.

They’re hard work.

For example, we still have some ongoing after a year despite multiple meetings, stages and days drafting contracts.

It requires an entirely different pricing structure and an OEM contract contains a greater degree of clarity on how support is managed.

They have the greatest value and take the longest time to confirm.

Interesting side effects

We didn’t think Upscope would become one of those companies with white papers and security pages. I think it’s important to have a personality and not turn into a corporate drone type company which is very tempting when faced with security conscious corporates.

The tone is important though. Having those white papers and security pages for people who ask is also a sign of respect, in that you take their issues seriously. Our tone on the website and in our emails has definitely changed though we’ve only adjusted it, not taken the heart out from it.

Tough SaaS questions: Answers to the 12 Questions that drive SaaS companies crazy

Enterprise SaaS pricing: How We Priced 3 Enterprise Software Deals

Why do Enterprise sales: Why SaaS Companies Realise they Need Enterprise Sales

Upscope's pricing mistakes: Upscope's Pricing Model that Worked

Show users your website like never before

Click to play with audio
Learn more about Upscope
Pardeep Kullar

Pardeep Kullar

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

Read More

Subscribe to Upscope Blog!