SaaS and Sailing – An Unlikely Alliance


SaaSing and Sailing 


When I’m not SaaSing, which does take up nearly all my time, I’m either sailing or doing something sailing related.


I’ve even set up a growing linked in group called SaaS Sailors. If you work in SaaS and are interested in sailing, follow this link –


I feel less guilty thinking about sailing in work time now as it is work after all! The fact is that SaaS and Sailing really have forged an unlikely alliance. Even Medallia, the well known SaaS company has made a major sponsorship move in recent weeks.


So, I’m just back from my Summer vacation with my wife, which, as you might have guessed was a sailing trip on our cherished sailing boat. (Think of the opposite to those stereotypical images you see on TV and boat shows and you get the idea)


The wonderful thing about sailing is that there is no better way so socially distance, and in 2 weeks, we came ashore twice to stretch our legs. It’s funny how walking feels a bit odd after a few days at sea.


For me anyway, Sailing, be that racing, or cruising and the SaaS business (in fact any business) are closely related. Here’s why….




As often the case, when I’m sailing, my mind sometimes drifts back to work and the metaphorical similarities between running a business and sailing.


Sometimes when I’m sailing and it’s all going well, I truly thank my lucky stars that I have been blessed to take part in such a fascinating and exciting pastime.


Being able to get in a boat and after a lot of preparation, if time permits, sailing to almost anywhere in the world is a thrill that I find hard to put into words.


The use of modern technology combined with traditional navigational and seamanship skills is a thrill for me and many others too.


However, when it’s all gone to poop, I’ve missed my tidal gate, a mechanical breakdown, the weather is closing in, or, as happened once when I was racing, my mind froze and I hit another boat, I ask myself why the hell I got involved in such a foolhardy and frustrating pastime! Maybe I should start stamp collecting? Ornithology even?


(I blame my Dad… with thanks!!)


Floor shows


In the same way, with my work and business, when it’s all going well, I am truly thankful that my opportunity in software found me as it did. I still jump around when a deal closes and have a small floor show moment to myself to celebrate good things. After 24 years, to still be passionate about what I do is important.


But, those bad times!  A deal fails to close, the new client that you thought would bring new opportunity, someone lets you down, Covid 19!!!!…..I’m sure that I am no different to many other people, it being natural human behaviour after all to think, “What am I doing here?” “I’m done!”, “to hell with everything” when things go the other way.


Those good and bad feelings, for me anyway, feel exactly the same whether I am on dry land or on the water. I guess it demonstrates passion in the 2 things that make me tick. But fortunately, in each case, it does not take long for my enthusiasm to return to “get things back on an even keel.


Sailing and Business Idioms


We were somewhere off the Cornish Coast 2 weeks ago and the Autopilot computer went pop. Hand steering from now on….and I started thinking about just how many idioms we use in business that are sailing related.


Look above – Get things back on an even keel!


Here are some more


  • Staying afloat
  • All plain sailing
  • Above board
  • Sailing close to the wind
  • Sink or swim
  • Keeping a weather eye
  • Don’t rock the boat
  • Show them the ropes
  • We run a tight ship
  • An all hands meeting (All hands-on deck)
  • On the rocks


I’m sure we all use at least some of these whether we are sailors or not.


Idioms aside, here are some other similarities


Preparation, Planning & Tactics


For me, it’s all about preparation before I cast off before a race or a cruise.  I can’t adequately explain just how important in the confines of this short article as entire books are written on this subject. The chances of winning a race or enjoying a cruise without planning are a fat zero. When we are racing (and cruising), tactics are critical to success so keeping several steps ahead of the here and now.


When I’m race helming, wind, tide, heading, sail trim and a myriad of other data points are all in my mind. Bizarrely, I hold this data as a picture in my mind and imagine a digital dashboard with all this data so I can try reacting to it instinctively. Well, that’s the idea anyway, helped of course by digital repeaters (and a computer) if its big boat racing or plain old feel if its small boat racing.

(This is my “data dashboard” illuminated when night sailing – There is a lot of data showing  – GPS, wind, depth, speed, batteries , compass, Nav lighting, Autopilot, AIS, multifunction display, full engine monitoring – ((Analogue still, I’ve not gone digital as yet on that – Yet!!)) – Not all illuminated as its blinding at night –  It’s a lot for a 10 meter sailing boat but what do you expect? I work in tech and I love tech but have a healthy lack of trust for all things tech on board!) 


Solid business preparation and planning is vital for any business and it will take a very lucky business leader to succeed without a plan, tactics or taking time to prepare.  As a business leader we all use dash boards and tech to process, what is often, large amounts of data to make better decisions to succeed and get ahead.


Great leadership leads to great teamwork


Unless you are singlehanded, (personal leadership) leadership on board could be considered to be the single most important consideration. With positive leadership comes crew cohesion and teamwork, meaning the crew will feel safer and more secure and will perform better. They will look up to their leader and want to be the best that they can be. Each crew member has something to bring to the party. Who is good with mechanics, health and well-being, cooking, sail trim, meteorology, navigation, tech, even humour? We all need a comedian on board!


The skipper identifies these strengths in each of their crewmembers and encourages them to work as a team to ensure they use their skills to manage the safe and optimum working of the vessel. The skipper needs of course to be aware and have some skill in all of these disciplines and more, but they can’t do everything, so delegation and clear and concise decision-making and communication is paramount.


How many times have we heard the story of the Executive that joins a company to do a job only to find that the leader won’t relinquish control? Imagine a time when poor communication in business caused an issue. Think about a time when team cohesion has been down. In business, it’s bad enough, out at sea it can result in loss of life!


Learning and self-development


Whenever I go to sea, I learn something. It might be my subconscious mind but every day at sea is a school day. Also, the importance of continuing to learn new skills and ideas through reading and practice is critical. I speak very openly that I started yacht racing after 30 years of yacht cruising, so quite late by most standards. That was a learning experience if ever there was, and it was a hard learning journey for me.


In the same way, in business we are constantly learning new skills. Be that a new technology, business process or even understanding a new client, the fact is that anyone who thinks that they know it all, no matter how accomplished they might be will start to fail if they close up the barriers to learning and development.


The maritime world has become highly technical with constant advancements in technology, making life at sea safer and reducing risk.  It is not an excuse to be a luddite and turn a blind eye to maritime tech as there are numerous safety considerations to consider. Essentially, boating in every aspect has also been massively influenced by the tech revolution in the same way as land life has also.


(PC based Euronav system that I use when offshore with full PC to NMEA integration – Bit of a sledgehammer to crack a nut and I prefer  Ipad Navionics for its simplicity and low power consumption) But the functionality is remarkable!)


In a similar way, if we stand still in the tech business, we get left behind and it becomes hard to catch up.


Don’t be afraid of a course correction


Sometimes when you are out at sea you have to deviate from your plan. For an inexperienced skipper, this can be an issue. They have meticulously planned their voyage in every theoretical way, but that plan has to be quickly binned and a course correction must be made as a gale is now forecast making the original plan untenable and dangerous.  Perhaps some gear breakage means that a port of refuge must be entered quickly. Maybe a critical tidal gate has been missed (As nearly happened to me 2 weeks ago)(( thankful for a powerful engine))


This does happen and the ability to have a new plan and safely change course must always be at the forefront of every skipper’s mind.


An all too real and ongoing example is the Covid 19 crisis. Most businesses across the globe had to very quickly initiate a new business plan and make course corrections in order to survive.


Knowing your strengths and weaknesses


In business, knowing how you match up to the competition is vital knowledge. There is no point wasting valuable time and energy in trying to win the unwinnable deal. Being aware of the financial and tax position of the business as well as the strength and weaknesses of your people are all critical to know in order to make good business decisions. Every business has an Achilles heel and knowing what it is before your competition finds it is critical.


In the same way, the sea will find your weakness – eventually, and, being aware of what your weaknesses are is absolutely critical for safe decision making. Often such a weakness might be poor maintenance that leads to gear failure. It could also be inexperience or a weak and tired crew that is unprepared for foul weather or a change of conditions. Every boat and crew has one, as do most companies, eventually!


Yes, always play to your strengths but it is folly not to consider and prepare for the converse of this also, be that in business, any sport and of course in sailing!




There are so many other discussion areas that I had considered for this piece, but I hope that the ones chosen to resonate and are not just the obvious, thus demonstrating how the sport of sailing and tech/business are aligned, in my mind anyway.


Feel free to drop me a line at about SaaS, business, sailing or any other conversation point that this short article might have triggered!

+ 44 (0) 1183 282008




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