About Rob Crossland

Rob CrosslandThe Background Bit

Hi, I’m Rob Crossland. I started life in Hull (it’s never dull) and began a career in IT by initially supporting “multi-user” accounting, payroll and sales order processing systems (sort of pre dates ERP but I’m not that old). Through that business I was exported to the sunny south and then into London and for the next nine or so years I worked for Olivetti, set up a systems reseller business with a friend, developed solutions for small businesses, worked for a help desk software business, tried another venture and ended up in Staffordshire. The failure of that last venture pushed me into freelance / contracting and I had some fun (and travel) working on projects for Railtrack, Fujitsu and AllTel. As a result of that experience I got interested in the technicalities of trading as a contracting (sad I know) and along with a colleague, we created Parasol. What we did different however was approach this as a process and systems challenge rather than tax and accounting. It was the time of the start of ir35 and the market was ready for simpler, less argumentative (contractor v HMRC) solutions. We conceived Parasol in late 99 and by April 2000 (and the start of ir35 or as some called it then, “the end of the world”) we were up and running with online timesheets, fast registration and a much easier to understand service (and a dodgy logo – see below).

It’s funny that my “career” had in many ways gone full circle, my knowledge of payroll (I was trained to do it manually) and accounting was handy along side the more latter experience in online systems. I didn’t know at the time but I was swapping my pure “IT” career for “Business” and an interesting future path.

The wheel is come full circle – Billy Shakespeare

Old Parasol Logo



The Parasol Group part

Parasol continued to grow and by 2005 we had gone from zero to around 5000 contractors being managed and revenues of around £132M. My original partners and investors had by now realised that we had built something half decent and we agreed that I would look at ways of repaying that investment and at the same time, lead the business to a new level of performance and offer. So by Oct 2006 I had learnt all about management buy-outs and became backed by Inflexion Private Equity. This provided an increased level of focus and professionalism that enabled the business to continue to grow and attracted not only investment (I make it sound simple, it wasn’t) but also some new senior talent to help me grown the business. By late 2008 we had done our first real acquisition when we fully acquired Quay Accounting, a contractor specialist based in Poole which thereafter became ClearSky Accounting (yes Sky TV did object to the way we designed the logo!). ClearSky accounting


The zig zag

I am sort of glossing over many of the challenges and hurdles but because we were always straight down the middle on being safe and reliable (and didn’t lead on tax) we were able to implement many a change with little outward disturbance. Managed Service (MSC) legislation didn’t affect us, we helped government understand the sensible reality of travel and subsistence expenses in the compliant part of the market, we consulted on many a policy debate, helped form a trade association, handled the Agency Workers Regulations, dealt with pensions auto-enrollment and much more. Our background in systems, integrations, processes and innovation have stood us in great stead. We have also always built a good culture and our various people centric awards are testament to that, especially Investors in People, Gold Status. We are also investing a lot of time and effort into a new generation of Optionis (who?) talent through our engagement in apprentices with over 30 in the group and growing.

Group hug

Having seen Parasol get a kid brother (ClearSky) we then added a baby sister in Silverline in 2010. So we had gone from being a single product in largely a single location to 2008 into a group of businesses with circa 150 staff. We had maintained growth in very tough conditions (or as the pro’s called it, “Global Financial Crisis.com”) and so started to think about how we could explain a little more cohesively what we did to those that were interested. Optionis was born (based on the Roman Optio – helper) initially as a group brand to explain the range of services we offered. Ok, so not the easiest name to get right but in reality it could have been called anything as the real service brands are and remain, the important bit. So fast forward to 2013 and we acquired some additional businesses, grown to over 200 staff, launched SME centric HR, Payroll and Accounting services and grown up a bit. In early 2014 we completed our secondary management buy out (SBO for short) and became partners with MML Capital, the impetus that has given us has been significant leading to further acquisitions and an emphasis on leadership development too.

It’s not been without many a challenge and I have learned a tremendous amount but equally it’s been very collaborative, team based and I’ve been lucky to have worked with some outstanding human beings.


Down time

As a bit of a geek and a lover of solution building I find myself getting involved in interesting and sometimes disruptive ventures. More on that later and you can see the portfolio on my about.me page. I try (not always well) to balance time obsessively working on stuff with family and sport. I have four great kids ranging from 24 to 5 so never a dull moment. In many ways my family is the driving force behind getting results and that is a combination of old school northern “provider” heritage and the fear of failure.

My position often gives me the opportunity to mix sport with business and none more than my role as part owner, Director and Vice Chairman of pro Super League side Hull Kingston Rovers. I now get my “relaxation” through supporting Manchester City but given I’ve supported them through some very down periods, I am not sure “relax” is the right word. Certainly an involvement in sport also allows you to consider the applicability of sport centric goals, teamwork and coaching into business (and vice versa).  The Hull KR experience is also very grounding given the part we play in a working class community and the challenges of being a business in a performance environment.


So that’s me I think, loads more to achieve and do – trying very hard for that to be on the basis of doing well and doing good.