Transformational Digital Operating Executive
Your Seasoned CEO / COO / Adviser

Founded Covestor, built Hailo, and led digital transformation at Travelex

A rare perspective on the digital landscape having played on both sides.

On one side, as an entrepreneurial agitator, creating disruptive tech enabled businesses and upending legacy industries.  On the other, as a leader of digital transformation within challenged incumbents. 

As a two-time founder and early employee in high profile venture backed technology businesses with two exits, Simon has consulted to startups and private equity backed businesses and led digital transformation for a leading global retail brand.


► C-level operating executive with 25+ years tech experience

► Managed multinational P&Ls with £50m annual revenue

► Launched, operated and scaled innovative digital B2C products / services in multiple sectors and geographies

► Led digital transformation of a mature retail business

Recent highlights

HAILO.  Transformed how people use ground transportation.
Built the first mass-adopted and market leading on demand ride-hailing business in UK.  Brought black cab drivers into the digital age and attracted a new customer demographic with Hailo trips taken every 6 seconds.  Created operating model to replicate across 20 cities in 3 continents in 2 years.

COVESTOR.  Created world’s first online investment management marketplace where clients can mirror portfolios of smart investors. Founded one of the early US-based peer-to-peer fintech start-ups.  Enabled discovery of and access to both professional and non-professional investment talent, provided aspiring professionals a platform to build institutional grade track records, and enhanced distribution for existing investment advisors.  Built team, product and infrastructure to operate within a highly regulated real-time environment.  Acquired by largest online broker dealer in US.

TRAVELEX.  Accelerated commercial outcomes from digital transformation for leading global retail brand.
Synthesised a multi-faceted and complex digital programme into a series
of prioritised deliverables, expediting desired outcomes and creating the building blocks of a digitally driven business.

LinkedIn and Twitter

What others say

"... leaves the Digital part of our business in a good place... provided clarity ... as well as a sharp focus on the key milestones..."  Anthony Wagerman. CEO, Travelex

"Simon was instrumental in building both the London business and laying the foundations for our international expansion..." 
Caspar Woolley. Founder & President, Hailo

"Simon is one of the smartest operators around... At Hailo he masterminded the rocketship growth of the UK through canny and can-do leadership. He is analytical and leaves no stone unturned..."
Carl Mesner Lyons. Ex-Marketing Director Hailo, OpenTable &

"I have rarely encountered such an individual who has such an impressive eye for detail coupled with an encompassing strategic vision..."
Mairtin O'Riada. Founder, Ravelin

Get in touch

Simon offers his expertise in a consulting and advisory capacity to both start-ups and long established businesses.  
If you'd like to explore how Simon may be able to help grow your business do get in touch