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Enterprise Gen Ai Leadership

I co-founded a Unicorn in Enterprise Gen Ai (Arria NLG), I'm a Partner at an Enterprise Gen Ai Consultancy (Meta-Morphix) and I help SaaS and Enterprise Gen Ai companies go global through SaaS Elevator and Kegai.

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“Simon Small is equipping future SaaS Leaders to win globally…”
Hamish Edwards,
Xero Co-Founder
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Invitation: Help Me to help you!

Serving the world’s finest SaaS Founders

From my time spent with hundreds of Software-as-a-Service (SaaS) Founders around the world, I learned few have the awareness, strategy and playbook to be able to drive their SaaS Business all the way to a $2bn valuation.

That's primarily why you see a lot of SaaS Businesses bought for $1bn and under. They opt-out and top-out too early.

That "$2bn valuation" is my vision for you: the day you reach approximately $200m annual recurring revenue (ARR).  What you do from there is up to you.

I’m committed to showing you how your SaaS can Dominate Globally so you can achieve your vision and absolutely smash it!  More importantly how to stay in the driving seat all the way.

What makes my approach unique is that I have lived it, built it and won a SaaS Category multiple times.  What's even better news for you, is that I've shown Founders the secret and now they are executing this approach in their SaaS Businesses.

The most common feedback I get from Founders is "you taught me to not settle, to go further than I thought and that I'm holding all the cards. That has been invaluable."

Today I am hand-picking Founders who want to take the same extraordinary journey. Are you up for this?   Let’s go!

My Story

What’s unique about Simon Small?

By the time I came across Software-as-a-Service, the company I was in, was discovering just prior to an IPO that it was in fact a SaaS company. 

The Founders of Diligent were noticing Salesforce CEO Marc Benioff talk about SaaS as a new industry.  They quickly realised that someone had changed the terminology and Diligent was no longer a software business using an ASP (Active Server Page) delivery model; but a Software-as-a-Service business.  We were one of the pioneers, proving the security and business model as an Enterprise SaaS offering.

By then we had about $1m ARR and ended up raising $24m at an IPO with a total value of $115m.  It was 2007 and we’d avoided an acquisition by Nasdaq and avoided investment from Venture Capital, preferring to stay largely independent and use the IPO as a major capital event.

Being unconventional in the SaaS world is all I’ve ever known.


We make Magic Happen for our Founder Clients

Matty Blomfield - CEO/Founder

“We increased the value of our business by several million dollars in 2021”

"Simon opened my eyes to the areas that build a SaaS business. He put each component into perspective, helped me understand where I'm at and what I can work on to make the biggest impact in our growth. His training was inspiring and we increased the value of our business by several million dollars in just 6 months. Together with Simon and his design team we built out our capital raising materials and Global Vision Document and closed out our round with momentum and over-subscriptions.  


Andrew Mayfield - CEO
Optimal Workshop

“We are on a clear path from $10m to $100m ARR”

"We are a $10m ARR SaaS business and working with Simon I can for the first time clearly see how we can and will reach $100m ARR. His impact is not just in sales, but shows up in how I view the business in its entirety. Simon is "The SaaS Whisperer."  Simon also helped us to build out our Global Vision Document which has allowed us to crystalise our direction and is proving invaluable in quickly closing our capital raise."


Rich McLeod - CEO/Founder

“Our Conversion Rates and ARR are significantly improved”

"Simon has changed the way we approach our SaaS sales. He reviewed our existing process and advised on immediate changes we could implement. Our demos are now so much more effective. Invaluable, practical training that is having a significant positive impact on our conversion rates and ARR. We are working with Simon to build out our capital raising materials and appreciate his valuable input to create a Global Vision Document."



Simon Says SaaS

Read My Latest ‘Thought Bombs’ to Discover New & Unique Strategies to Dominate Globally

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SaaS elevator - another level of SaaS

SaaS Elevator carries  Founders Higher

I have poured 15 years of expert SaaS execution across 5 continents into a series of Mastermind Training Programs that will help you Dominate Globally with your SaaS until you reach your $2bn Exit Day (when you sell/merge with $200m ARR).

There are no prerequisites for coming on the journey. You could be ready to start or sell your business - or somewhere in between. Either way, what you learn here is as simple as the rules of real estate. For the first time they have been distilled and taught in a way that is both accessible and applicable.

Our vision is delivering what is possibly the finest training for SaaS Founders anywhere - and we like being the best kept secret!

Waiting can be costly.  SaaS Business success at the highest level is elusive. Most fail to dominate in global markets and that caps their growth.

What we do best at SaaS Elevator is unlock the magic in your vision and help you amplify the power of your SaaS Business so that everyone feels it: your investors, board, customers & team. At SaaS Elevator we work on the whole picture so that it becomes a sensation that draws investment toward you.

We take you higher. We have your back!

Find Out More

Voice of SaaS

Media comments from Simon contain his unique and refreshing global perspective.

As a seasoned deal-maker, Simon is available for comment on major Technology acquisitions that have hit the headlines.

He also speaks on how to create significant economic benefits to regions through understanding how to grow Technology ecosystems.

Simon provides insight into social media, cyber-security and governance at the world's biggest corporations. He has  featured on the front page of the Financial Times of London.

Other topics Simon can comment on is the rise of Artificial Intelligence (Natural Language Technologies), Livestreaming, and NFTs.