Jonathan Holloway, Consulting CTO

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How do you work in an interim capacity?

I typically work in one interim role at a time. That involves three to four days working with companies and their product/engineering teams on-site predominantly. I use my other day for fractional work and startup advisory.


How do you work in a fractional capacity?

This might involve one day a week or a few days a month depending on the problems the company is trying to solve. I usually work with existing teams, analyse specific problems, set goals and coach teams towards those. This is on-site.


Why do I need a CTO?

The role of the CTO is often confusing and very different depending on the stage of company. There's a good article by McKinsey consulting on the subject - Why you need a CTO


How is it different to a head of/VP of engineering?

I believe that CTO's at a point in their career in a company make a choice - either to remain hands on/technical or to move more into a people management/product strategy role - Defining Roles - CTO and/or VP of Engineering


What problems do you work on?

I've worked with the following problem areas, but please get in contact if you have something other than this.


My CTO/lead engineer is leaving

In the unfortunate situation whereby your most senior product/tech is leaving I can help with bridging the gap until you find the next person. In some situations it's necessary to understand why they have left and solve the root cause or set of problems that led to the situation.


"I need to build a team in-house to build out the product"

I can help with building a product and engineering team from the very beginning of the company journey. I help founders find the right product/tech people and also advise on when the right time is to bring in specific roles to the business, including a CTO, VP/head of engineering, devops engineers etc..


I need to bring a product in-house from an agency

It's great having an agency build out a product for you, but there are lots of questions that should be asked prior to the build of a product. There are also key checkpoints and ways to ensure you build a scalable product or platform from the beginning, rather than it being an after-thought. I can help with the rescue of products/software when things have gone awry, I can also help put a team around the product when you bring it in-house.


I need to grow my team, but not sure how to do this effectively

Building product/engineering teams for companies can be hard, especially if you just have engineers who need help with identifying gaps, weakenesses and strengths. I help by providing support here. I can also carry out a review of the team and propose hiring plans. I can also help with team structure (where it's needed) and where it compliments the product/platform you're building.


I think my team need help

Your team might have told you directly or you might sense this based on problems in the day to day running of the business. I help with transformation of people, process and product to solve issues that people might be having.


We're having issues with delivery

There's a common problem with project delivery in the software industry. This is a non-trivial area in-which I can help a business identify what they're delivering, and the issues with measurement around delivery. This might be because of issues around communication, specification, interface between product/engineering, wasteful practices, measuring the wrong metric or something else. I can help with identification and resolution.


We're not sure how to structure the team for growth

I help you to understand the existing team, the interfaces between it and the rest of the business and what type of structure might be suitable. This includes hiring where there are gaps in technology, process or capability. I also look at identifying roles people are playing in the team, providing help on items such as architecture, devops etc... The individual contributor vs manager split is often mis-understood here.

We'd like to outsource functions or parts of the software

Outsourcing isn't quite as straightforward as it sounds. There are many challenges/hurdles to overcome, especially if the team haven't done this before. Should you outsource parts of the product or specific roles (e.g. testing)? I can help with the outsourcing problem, preparing the product/engineering function for outsourced projects, help identify potential agencies and make the ride a little less bumpy.


We're having issues with quality

Understanding how you specify what needs to be built and how you build that is key to understanding quality as a non-functional attribute. I can help you understand where the problems lie and how to address these.


Product Strategy and Execution is harder than we thought, help!

There's often a gap between product and engineering in terms of communication, specification and execution of projects to meet goals. I can help with the product management side here in terms of specification, forecasting models, estimation, how to validate without building etc...


Development/Release Management Processes

I've seen many different process models over the years - from waterfall to RUP to scrum (and other agile methodologies). There are pros/cons to all of them so I can help to understand what you have today, what is working/isn't working, change management and pragmatic adoption of process (rather than carte blanche Scrum by the book).


We want to ensure our product/processes/people are good for a funding round or potential acquisition

I've done lots of due dilligence around product and software in terms of understanding the structure, how it maps onto business process and product features. This is often for companies wanting to bring something in-house, for funding rounds and potential sale.


Other Problems

This is not a definitive list of problems. If you do have other problems you need help with them in get in-touch with me and ask whether I can help with them.