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Will Steward

Advisor United Kingdom, GB

CEO & Co-founder, Cobloom. Previously MD & Co-founder, Iconsive.

CEO & Co-founder, Cobloom. Previously MD & Co-founder, Iconsive.

4 vouches

Involved In


Iconsive (now Cobloom)
Pint Drop
File Den


CEO & Co-founder Cobloom January 2016 - present
MD & Co-founder Iconsive (now Cobloom) October 2012 - January 2016
CEO & Co-founder Pint Drop October 2010 - October 2012
CEO & Founder File Den April 2006 - July 2011
Consultant Zoombu March 2010 - September 2010


University of Warwick Computer Science & Business Studies 2010 - 2011
Aylesbury Grammar School 2002 - 2009

Interested In

Advisor With
  • • Hiring
  • • Professional services
  • • Recruiting
  • • Financial planning
  • • Business Management
  • • Company Culture
  • • Startup Operations
  • • Strategic Partnerships
  • • Startup finance
Markets of Interest
  • • Enterprise Software
  • • Data & Analytics
  • • Cloud Services
  • • Productivity Tools
  • • Financial Services
  • • Advertising
  • • Mobile
  • • Small Businesses

You Should Know About Me

Key Strengths

Marketing • Content marketing • Lean startup • Web Development • Growth hacking • B2b marketing • Digital advertising • Business Strategy • Customer Success • Entrepreneurship • Organic Growth • Product Marketing • SaaS sales • Strategy • Agile Project Management

Key Accomplishments

Founded my first company, File Den, age 15, while in school. Alongside growing the company, I achieved straight A's at A-Level. I grew the business from nothing to over 3 million registered users, hosting tens of millions of files for consumer & business customers worldwide. I managed a fully remote team of contractors who developed upon the software I initially built, and optimised our systems architecture. In 2011, File Den was acquired by CX.

During 2010-2011, I negotiated the sale of File Den with several potential acquirers, and experienced the pain of due diligence, plus "good as done" deals that fell through in the final stages of due diligence.

I co-founded my second company, Pint Drop, in October 2010. I developed the product, a mobile app, and managed the development of a piece of Chinese hardware, which validated drink vouchers behind bars in pubs & restaurants. In Summer 2011, I left university to focus on Pint Drop full time. We raised a seed round that Summer, to build upon our early success attracting pubs & bars into the Pint Drop "Text Your Friends a Drink" scheme.

Ultimately, in October 2012, the company was dissolved. After numerous pivots and changes in strategy, it proved too expensive to penetrate the restaurants & bars in our target market at scale, while simultaneously building consumer interest in our vouchers.

Since then, I've been working on Cobloom. We partner with SaaS Startups to help them achieve Product/Market Fit faster, then build a revenue generation machine that scales, by improving their sales, marketing & customer success strategies. The company is now profitable.

How I like to work with people
As an Advisor

Above all else, I like to listen. To understand the market, solution, and the entrepreneur's perception of where the biggest opportunities and challenges lie. After building up a good picture, I challenge assumptions which the entrepreneur may not have considered.

I believe in supporting entrepreneurs to come up with their own solutions to their problems, by sharing my personal experiences & knowledge, gained from founding Startups myself, and helping other Startups to grow. I help people to focus on what really matters, and ask the right questions, rather than providing shallow advice which doesn't benefit from the entrepreneur's unique depth of context.

Particular areas of expertise: SaaS, marketing, sales, customer success, growth strategy, company culture, early-stage investment (seed and earlier), startup strategy

People often say that I have a particular knack for coming up with simple solutions to seemingly complex problems: by taking a step back, looking at data, patterns and trends, then "connecting the dots" in novel ways. Where many see impasses, I see opportunity, and love helping to build innovative companies which disrupt industries.

Vouches Received

Vouches Given

Think Will is awesome?
Vouch for them.

Martin Steward
We worked together  •  CFO & VP Consulting, Cobloom and Operations Director, Iconsive.
Always looking for new ways of doing things. Gets excited about disruptive solutions and quickly sees markets for such solutions. Analytical ... , always reading and likes to approach projects in the best way. A great innovator and business leader.
Stevie Brooks
We worked together  •  Founder & CEO, CloudCustom. Previously Business Development Executive, 64TEQ.
Not only is Will extremely knowledgeable about how SaaS companies and Startups can increase revenue through inbound marketing he also offer ... deep insights when it comes to being an entrepreneur.
Michael Eckert
We worked together  •  Global Market Segment Leader - Corporate, Milliken & Company. Previously Value Stream Manager, Acuity Brands. North Carolina State grad.
Will has proven to be an extremely useful thought partner. He's very good at prioritizing ideas and clearly presenting the impact each may h ... ave in order to come to solution. Beyond the strategy Will is also great at getting to action quickly. He's very action oriented and great at keeping me and my time on task and on schedule. Bottom line - great guy, great mind and a joy to work with.
Ryan Law
They're my current cofounder  •  CMO & Co-founder, Cobloom. Previously Content Strategist, Iconsive.
Will has been my advisor and mentor for over 5 years, and his advice and experience was instrumental in helping me start my own venture. Sin ... ce then, I've joined Will as a co-founder, and his guidance and SaaS-expertise (having built, marketed and sold his own SaaS solution) continues to be invaluable to my own personal and professional development. Smart, thoughtful and honest, Will is always willing to go a step beyond to help his mentees succeed. (He's also great to share a beer with!)

Stevie Brooks
Founder & CEO, CloudCustom. Previously Business Development Executive, 64TEQ.
Stevie's the first person outside of our company working in sales/business development that has really impressed me with both his approach, ... and trust-building transparency. He has a thorough understanding of sales, data acquisition/enrichment, and an account-based approach which when combined with the latest sales tech, is particularly effective in the mid-market and enterprise. He's a born entrepreneur, not afraid to go big, and continually developing, testing & reflecting on all aspects of his business, and self.