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My story...

I have been fortunate to have had two extraordinary parents who taught me the power of encouragement and enthusiasm as well as deep analysis and creative execution on dreams that matter.

In the technology world, my focus has been on Software-as-a-Service (SaaS) for 15 years and I've fallen in love with the business model and the art and craft of creating a global category leader.

Prior to this I was pioneering the world's first interactive TV at BSkyB for Sky Sports in London, setting up regional TV in New Zealand and co-Founder of Pacific Underground (New Zealand's 30 year old iconic Pasifika theatre company).


Before SaaS ...

By the time I came across Software-as-a-Service (SaaS), 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 the Diligent Founders had declined an acquisition offer by Nasdaq and  investment capital from Venture Capital (VCs), 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.

Formative SaaS Years

I was fortunate that Diligent was ahead of the SaaS market and many cite it as the gold standard in customer service, not just for SaaS but for any business (a seven second response time around the world for any customer enquiry, helped it win Gold several years running at the American Business Awards).

At Diligent I was Managing Director for UK, Europe, Middle-East & Africa, responsible for go to market, sales and customer success.  We perfected the model of working with the boards of the world’s largest corporations, from creating awareness, to initial engagement, being evaluated against the competitors, conducting rigorous security reviews and onboarding and training with a 24/7/365 support desk. 

It was not all plain sailing, and what I’ve learned is building a category leader like Diligent is intense and hard work.  We won; deal by deal, FTSE100 board by FTSE 100 board.  Today there are 200 people in Trafalgar Square in London and Diligent is the world’s number one Compliance, Risk & Governance SaaS provider. According to its Private Equity owners, Diligent is on track to hit $1bn ARR (potentially becoming a $1tn SaaS Business).

Arria NLG formation

I met the co-Founder of an extraordinary Artificial Intelligence business at a funeral (of all places), in London in Nov 2021.

It was clear from speaking with Ian Davy that what his company, based at the University of Aberdeen, had their hands on was potentially the most incredible (and largely unknown) branch of Artificial Intelligence called Natural Language Generation (NLG).

Within a few months, together with the Diligent founders, we formed a company called Arria NLG to fund and take the Natural Language Technology breakthrough innovations that Ian and his co-founders had created, to the world.

Arria NLG eventually acquired the Data2Text company of Ian and his co-founders and it was listed on the London Stock Exchange (LSE), before being taken private. Now it prepares for an NYSE listing in 2023.  Arria has raised $170m to date.

Turning Away from SaaS

After leaving Arria NLG in 2015, I was setting my sights on Moonshots, becoming part of Peter Diamandis’ top CEO group called Abundance 360 in Los Angeles and flying around the world meeting influential people and exploring exponential technologies. I accepted an opportunity to attend Necker Island, Richard Branson’s private island in the Caribbean (that's another whole story). I even met Gary Vaynerchuk here at SXSW, in Austin (not that I knew who he was!).

I became focussed on the future, I started thinking of myself as Futurist.  What could life be like in 5-15 years time with all of the evolving exponential technologies. But over time I needed a change. I asked myself what would I really love to focus on and where could I add a ton of value, and the answer came back as four letters: SaaS. So I retired as a Futurist.

My Return To SaaS

Over the summer of 2020, I contemplated my destiny. Having worked in many industries and with a lot of options available, I questioned where I wanted to focus and make an impact.

I realised that SaaS was it for me.  An industry that transforms business and communities, creating wealth and opportunities along the way.

I chose to teach what I’ve learned.  To show SaaS Founders how important it is to be Category Leaders; the unconventional Capital Pathways available; and the mastery required to drive revenue for a SaaS business to become a juggernaut.

So I began to create Mastermind courses that would help SaaS Founders.  Over the last 2 years, I’ve livestreamed a show called “SaaS On the Street” and started SaaS Elevator to teach my SaaS Founder Curriculum on Strategy, Capital and Revenue.

Getting Back on the Tools

One of my clients at SaaS Elevator, Optimal Workshop, hired me as a Chief Revenue Officer (CRO) to drive improvements in revenue over 15 months.  I’ve implemented a transformation program across the whole revenue function to embed best-in-class practises.  I’ve found it refreshing being back on the tools, to create this powerful foundation that will drive it towards juggernaut status.  

Used by the biggest companies in the world, Optimal Workshop is the category leader for information architecture.  While I’ve been able to implement my frameworks, I’ve also drawn on what Optimal Workshop has in its toolkit (as a Freemium-Enterprise offering with a large amount of self-serve revenue that’s been a SaaS pioneer of Product-Led Growth for 15 years).

The result from being CRO at Optimal Workshop is that the  Curriculum from SaaS Elevator is more relevant, more up-to-date and richer for all of this recent hands-on experience.

Here to serve...

For me to be happy, you have to be winning in your SaaS business.  Not against solely revenue metrics yardsticks, because they never take into account the awareness in the market and how you are growing your category.  Winning against the best possible outcomes this quarter.

I’ve learned that the “quarter by quarter” advancement is what really matters in SaaS.  How did you do last quarter, where are you this quarter and what’s happening next quarter?

Becoming not just the Category Leader globally, but the Voice of the Category; defining and expanding that Category.   The secret to my success is being able to walk in a Founder’s shoes - including ALL of life’s struggles.  Nothing is off the table to be shared and sorted.

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Feel free to use the box below to get in contact about anything that's going on in your world. I read everything.

“Simon Small is equipping future SaaS Leaders to win globally…”
Hamish Edwards,
Xero Co-Founder
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