The CTO, The Agency and The Appointing Business: Top Tips for Senior Jobseekers

Having worked at Talent Point for over a decade I believe that the gap between customer and recruitment agency has never been wider. Empathy is critical to the success of the job seeker, the agency and the appointing business, yet the three-way relationship rarely creates it naturally – effort and trust are required from all three parties to achieve mutually beneficial outcomes.

As leaders in their field, CTOs set standards for all those who work within their teams. For me, the way a CTO feels is how their team should feel, with their vision for technology being the driving force behind every technology initiative, standard and behaviour. This should extend to both recruitment and job seeking. The way CTOs look for work is often similar to how less-senior technologists look for work and the interaction between CTO and recruiter being the measuring stick for mutual success.

Many CTOs, unfortunately, are not helped by recruiters who typically aren’t senior enough themselves to have real empathy with what a CTO actually does. CTOs, in turn, lack real guidance on what these recruiters need from them to deliver a painless, informed service that results in access to the best opportunities.

Recruiters are far from perfect. Many are just chasing targets and see time spent with applicants as an obstacle to this, but many others are simply under huge time pressure and have no choice but to cut certain quality corners they wish they didn’t have to. It is important that CTO’s understand the pressure recruiters are under, how this can affect their capabilities and showing empathy – not frustration – with their situation can benefit a CTO in finding work.  

When I place an advert for a CTO I will on average get between 500-1000 CVs over a single week as well as numerous LinkedIn messages from my existing network. I can also receive up to 10-15 calls a day coming into the office. Most of the CVs I receive are either not relevant or are lacking a piece of information critical to my initial screening. At this point I have almost no choice but to delete the application. Not ideal but true. As much as I would love to call everyone and feedback, there simply is not enough time in the day to do all the feedback and find customers the CTO their business urgently needs. To break through CV screening stage against such large odds is surprisingly easy. Here are my top tips for creating engagement at CV stage of the hiring process.

Top Tips:

  • Address – put a location on your CV. It doesn’t have to be your exact address but “London” does help. I must know where you are and that this role is within your sphere of interest.
  • Chronological order –make sure that your work history is in chronological order. Many CTOs put projects at the top of their CV but they don’t explain whether it was done 10 years ago or yesterday. They also don’t explain which company they worked for at the time. This info is highly relevant and is how I put experience in context and formulate interview questions. Without context our interview is going to take five times longer because I need to establish it before I can start gathering meaningful examples. This is particularly critical for CTO roles as the situation is intrinsically linked to suitability.
  • Don’t apply more than twice – If you send your CV more than twice it tends to ring alarm bells in my head as I think that you aren’t reading what I’m advertising. Just like CTOs don’t want to work with “spray and pray” recruiters, the boards and CFOs I represent don’t want to work with “spray and pray” CTOs.
  • Attach a CV – make sure you attached a CV not just a LinkedIn profile or just an email with achievements. LinkedIn rarely has enough info and I may be reviewing CVs on my phone. I also believe that if you are serious you will have taken time to write a CV and this leads me on to my next point.
  • Tailor your CV to the role. – Please do not write Programme Manager, COO, CMO or CEO and then claim to be a CTO. Whilst you may be able to do this role it is unlikely you pass the interview because the bulk of it will be spent trying to map your experience in a non-CTO role to what a CTO typically does. If you’re a strong CTO then I would expect you to be a CTO and to have tailored your CV to the role you are applying to. If I list projects and initiatives the role will entail, please bring these to the forefront of the CV you send me – it gives me instant context and I know a 30-minute call will yield meaningful information.
  • Talk about technology – In this day and age CTOs are “Technology people” and it is expected they are close to tech. Whilst you don’t have to be coding in your CTO role (and you shouldn’t if you are a true CTO) we still want to know which tech stacks you have worked with. Vague answers to the effect that “it’s about business, tech is merely a facilitator” neglects the risk associated with hiring a CTO into a JavaScript environment who is used to motivating and vision setting in a .NET one. The business environment and culture in these teams is as different as the technology base and I’m going to have to establish that you realise this and can adapt if needed. Help me do so by telling me about the technology your teams use.
  • Size of team – This is something almost everyone misses, and I see as vital. I need to know if you have been managing 5 people or 500 people. It makes your experience very different and likely your skill set too. Please include as much as you can around size and structure and types of people in your team. This will also give me extra info I need - for example do you have Scrum Masters or DevOps staff. This will tell more about the team and environment.
  • Send a personal message – If you really have read the advert properly and think you are an exact match then I would advise stating why in a LinkedIn message or email. Nothing sways me to work with a CTO more than them showing they treat situations as unique. Applying for a job and trusting that I have represented that job accurately enough for them to speak to me about their suitability says a huge amount about their skills and ability.
  • URL or Description of company – This is another classic mistake most people make. Domain knowledge is often highly desired by my customers and with 1000 CVs to review, if I see a company I don’t recognise (and it does happen) and there is no URL or company description it makes it very tricky. I simply don’t have time to Google and try to work out if I have the correct company. Ideally put the company website and a brief description so I can see if it is relevant.
  • Don’t put too much information on CV – This sounds obvious, but CTOs have often done quite a lot in their career but please be selective on what you write in your CV.  Each to their own but I think 3 or 4 pages of nice spaced out well formatted content is perfect.
  • Apply in the first 2 weeks of an advert – Leading on from the point above. I would usually have picked my top 10 in the first 2 weeks so if you apply after that it is less likely you will be chosen. Unless you follow ALL the points above and then you still have a good chance.
  • 10 second read / 1 Minute read – Due to so many CVs, recruiters sometimes have to scan the first page in 10 seconds and then make a call on whether to do the 1 minute read, then this can follow on to a call. Try to get the important info on the first page and by this I mean the last 5 years of your work history. Most recruiters will go straight to the first role so make sure it is on the first page.

I hope some CTOs find this helpful. It is not an ideal world I work in but follow these tips and I promise you will be saying far more about yourself than you think. Tailoring an application tells a recruiter so much about how you operate – personal vs generic – and makes them able to invest time in you. Adopt the above and you will always do this.

Best of luck our there!

Simon Mortimer
Talent Point


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