Last updated on July 6th, 2023

Lessons learned: Enterprise SaaS Sales

Pardeep Kullar
Pardeep Kullar
Lessons learned: Enterprise SaaS Sales

This lessons learned series is part of our live SaaS resource list we're
building while launching a new product.

What one sentence from blog posts on enterprise sales was most important

and why?

"As tech co-founders we buy software entirely differently to enterprises."

As co-founders, we initially bought and tested out a lot of software of which
90% is less than $100 per month.

I've recently used Oribi, SEMRush, Slack, Camtasia, Sublime, RoamResearch,
Ghost and half a dozen other tools. The only company where we spoke to a
person in any form of trial or demo was Oribi and that was a single demo
followed by a trial and purchase.

Now compare that to how an enterprise deal can go:

  1. They email us asking for an intro to the right person at our company to
    handle their requirements.

  2. They ask for a demo.

  3. They ask for additional documentation.

  4. They evaluate the product compared to other products.

  5. They ask for a 2nd and 3rd discussion on pricing, security and features.

  6. There are ongoing discussion with their technical team including a separate
    slack channel set up for them.

  7. They ask us to fill in a 200 line security form.

  8. There is a 90 day 'Proof of concept' to complete.

  9. There are NDAs, service agreements and contracts to sign.

  10. They make requests for small changes to existing features.

  11. There are requests for further onboarding documents or videos and training
    of key staff.

This whole process can take from 3 months to a year and sometimes longer. Each
deal varies. Some can be done in 2 to 3 months and others can drag out over 18

That's why it's hard to adjust to enterprise sales. We don't think that way
naturally until we ourselves buy expensive software which requires a deeper
commitment and thought given to how it will change internal processes across

What dumb assumptions did we make about enterprise sales at the very start

of our SaaS journey?

That enterprises would sign up and try the product first.

We had not considered a company would ask questions, want demos, want further
security and comparison documents sent to them, over months, as part of their
evaluation process.

It did not fit our mental model so it was hard to understand why they didn't
just sign up and try it rather than asking all these questions.

What's one the most worthwhile things we did after this?

Security is a big problem for enterprises and many deals involve filling in
security forms or answering security related questions.

Getting all our documentation in place including security docs, MSAs, pricing
contracts etc helped speed up this process.

Of course, getting ISO certified and now going through the SOC2 process has
been useful. It not only gives us a way to make a more secure product but
provides us with instantly accessible and shareable security docs.

What would we advise someone to do if they were starting enterprise sales

from scratch?

Hire a sales exec with experience in enterprise sales.

Initially, we as co-founders, do sales and are passionate about the product
but we're not experienced sales people. If you listen to an experienced sales
person working on an enterprise deal it's almost as if they're talking a
different language. When we started we didn't even know what POC (Proof of
Concept) meant.

If we had a magic wand how would we use it to improve our enterprise sales


We keep hearing the advice on the benefits of hiring a VP of sales (assuming
we are at the right level for it). Someone who would run a department and be
able to recruit great sales execs. Someone we can trust to run things so we
can focus on the next immediate priority within product and distribution to
bring that VP more high quality leads because we trust them with leading the
team to manage those leads.

Pardeep Kullar
Pardeep Kullar

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