Rob Green: Fractional CTO Q+A

Bio

Welcome to our latest Fractional Q&A post featuring Rob Green, a strategy and product-focused technology leader with 20+ years of industry experience.

Rob works with small-medium business founders and leaders to shape digital strategy, scale and mature capabilities, and advise on how technology can support business growth and customer experience. Rob has a strong interest in organisational change and psychology, with a passion for helping teams collaborate and deliver against strategic goals.

Complete this sentence as concisely as possible, “I am a… “

I am a fractional CTO with extensive experience in digital consultancies and businesses: growing digital and technology teams, setting technology strategy and architecture, ensuring integrity and optimising delivery methodologies.

Are there any other titles/terms that people commonly refer to you or you refer to yourself as?

Technology Advisor, Technology Consultant, Technical Director, Coach. It varies based on the length of an engagement with a client, type of work (advisory, projects, interim, coaching, etc), and occasionally existing structures (no CxO titles). Also may need to be respectful of an existing CTO that needs guidance or support, to avoid any confusion in roles.

How would you say you stand out from others that do a similar job?

As a fractional CTO, technology is just one part of the tool kit needed. To be effective the key strength I rely on is communication, bringing technology teams closer to business stakeholders, limiting misunderstandings and ensuring everyone is working towards the same vision.

I’m interested in business strategy and organisational psychology; I make time to listen to the key stakeholders, asking questions until I fully understand the drivers in a business and how these are shaping requirements, presenting back challenges, working towards ensuring everyone has shared and clear vision, and that all teams have been able to, and continue to communicate their needs effectively.

My deep background in technology wins the trust of the engineering teams that I work with, but my preferred approach is always one of building ownership and autonomy in teams, ensuring that the talented people that have been hired into an organisation have their voices heard and are motivated to contribute to the success of the business.

The most enjoyable challenges for me are the ones where I’m working with open and frank founders or leaders of businesses going through a transition. Perhaps their product or service has launched to market, already has interested or paying customers, and is at the milestone of having received or seeking funding for increased growth. This is when businesses need support in where to invest in digital, how technology can help them to scale and also begin to mature from start-up behaviours whilst still retaining a culture of entrepreneurialism.

We are keen to know more about your work as a fractional. Could you perhaps share a few details about projects you have done in the past?

The most rewarding engagement since moving to fractional roles was with a disrupter in the property development space; having launched a concept co-living space in London they were scaling rapidly with a mix of projects underway in Europe, acquisitions in the US and 20+ new developments globally, attracting significant investor interest and with large raises in the pipeline.

The brief was to support the non-technical founders and leadership team, take stock of their technology investments and strategy, assess the integrity of the platform that powered the co-living operations, and work with key stakeholders to understand the challenges the business would face as they scale, including consistency of customer experience and operational processes across multiple regions. I had to be investor-facing to showcase how technology was differentiating the co-living proposition. I was also tasked with shaping the role of a future CTO and assisting in the selection process.

The business had pressing needs, a large number of projects were ahead and the pace of openings was rapid; there needed to be a longer-term strategy behind the technology that would be enabling staff and providing customer experiences.

The co-living resident's experience was being brought together in a mobile app from which they could interact and manage their entire stay; from the initial application process, add-on guest services, restaurant ordering, access to rooms and spaces, booking out communal areas, in-room entertainment, community interaction and events and much more. Achieving this seamless experience required thought and investment into all the technologies being used in the building, as well as all of the operational systems and processes.

Some key accomplishments in this engagement were setting a standard technology blueprint for all new co-living projects and testing some of them in a new London-based flagship; rolling out new standardised systems to optimise in-house team operations (enabling streamlined task management for facilities, cleaning, front of the house, guest requests); roll out of restaurant systems (stock, menus, payment, ordering) and the development of business intelligence dashboards underpinned by a data warehouse bringing together metrics (customer marketing, customer engagement, occupancy and revenue, operational insights etc).

Is there anything you’d share with aspiring fractionals?

Learn to productise the best bits of what you do: if you want to stand out from your peers then you need to present a clear understanding of where you’ve excelled in the past and how that’s informed a set of services you now provide to support organisations as a fractional CTO.

Have a clear view of the benefits of fractionals: don’t be surprised if sometimes when discussing a fractional role you are suddenly offered a permanent position by the organisation and they may not settle for less. If you want to stand your ground, you won’t be able to rely on just the cost saving and need to think more about the role played in this phase of their journey.

Explore niches that work well for you: it could be a particular phase of a business, specific industries that you have more aptitude for, areas of technical expertise and so on. Focus on the things that you’re strong in and build on your reputation.

Keep learning: one of the magical things about being fractional is that you’re open to exposure to ways of working in multiple organisations at once and can learn from these; don’t forget to broaden your understanding of different models and approaches to business challenges, respect the journey that your clients have been on, and use your experiences not as a template but as resources to help them grow.

In conclusion, Rob Green is an experienced Fractional CTO, Technology Advisor, and Consultant who excels in shaping digital strategies, scaling technology teams, and optimising delivery methodologies. Rob's background in technology earns the trust of engineering teams, but he prioritises building ownership and autonomy within organisations. He thrives on challenges posed by businesses in transition, particularly those seeking to scale, mature, and retain an entrepreneurial culture. With a track record of successful engagements, Rob has helped organisations assess technology investments, streamline operations, and enhance customer experiences.