Kyle Richless

Hi - I'm Kyle!  A barred attorney by trade, albeit one who has never practiced a day of law.  Go figure!

A decade+ ago while in law school I joined a bar review upstart as its first sales hire.  At the time, it was a simple means to accrue some extra spending money.  But this first taste of sales and Startup Land got me hooked and served as a launching point for what has become my vocation and professional focus:  implementing and optimizing revenue teams in the context of privately-held, venture backed startups.  

Post law school I joined Benchmark-backed Axiom Law -- a 2-sided marketplace purpose-built to deliver legal services in novel and groundbreaking ways -- and a key player in the first generation of the Legal Tech space.  I've spent the better part of 7 years at Axiom in various sales and commercial leadership roles.  While I've worn a few different hats, there was a constant thread and focus:  optimizing for World Class Talent and building Top-of-Funnel predictability.

Axiom made for an invaluable crash-course on all things sales, marketing, G2M and people leadership.  It provided a forum for me to make all the mistakes while building a commercial organization totally from scratch, and then exposure riding heard over a global function while navigating through the Messy Middle of the startup lifecycle.  This culminated with the awesome, on-the-ground experience of executing a liquidity event and ownership transition -- in 2019 we publicly filed our S-1, only to change course and sell to Permira, the global PE fund, months later. 

To say it was a wild ride would be an understatement. 

Meanwhile, over the past 4 years I've had a ton of fun with my "side hustle":  consulting for and personally investing in privately-held startup ventures.  I generally stick to my knitting and am disciplined about jumping in only when I have a ton of conviction I can add real value, in a hands-on way.  So I look for one of the following 5 elements to be present before saying yes to a new consulting or investing opportunity: 

(i)  Transition from Founder-led sales to early commercial build

(ii) Defining the sales/marketing marriage, including which function should own G2M Primacy

(iii) Top of Funnel emphasis - lead quantity, quality, & consistency (in service of revenue predictability)

(iv) 2-sided marketplace business models OR startups which play in the greater legal tech ecosystem

(v)  Efforts to upgrade commercial talent complexion & the increased ROI from World Class Talent  

In practice, I'm called on the most for (v) above.  That isn't a surprise, as I wholeheartedly believe that finding and betting on great people is The Only Strategy -- and increasingly so in today's accelerating, hyper-digital era.     

Ever the workaholic, I also serve as an Operating Partner at The Legal Tech Fund, the first early stage, legal-dedicated venture fund. TLTF has provided additional opportunities to get in the weeds with Cream of the Crop startup operators, and to learn from a pair of uber-talented Fund Managers. 

Finally, I love to soak up other's learnings and habitually commit time to absorbing content from folks whom I admire - whether VCs, Operators, or G2M/Sales/Marketing Leaders.  I'm a staunch believer in the idea that feet-to-the-fire learnings are accelerated when complimented with external thought leadership & best practices.  

A desire to promote and share this ideal - combing inside and outside learnings to supercharge personal and professional growth - was the true genesis of this blog.  As such, The Revenue Trend is designed to create and surface content which can amplify day-to-day experiences and plug gaps in Founder's experience, knowledge-base and skill set as it pertains to sales, marketing and G2M strategy.  

Message me on kyle@legaltech.com for any inbound inquires, consulting, investing, or otherwise.  

Hope you enjoy the blog!  

Kyle Richless