Recently, we had Emily Castles, CTO at a scaling start-up, Boundless, joining us for her fourth CTO Shadowing session. She reflected on their journey over the past year and, by doing that, provided an exclusive look into the challenges of a scale-up Chief Technology Officer who has to recover from severe financial cuts and consequent team losses.
A year before, the financial cuts at Boundless affected product and tech teams. The product team especially suffered and was reduced to virtually nothing. At that point, of the original eight team members (a full development team with a product manager), only she and one other developer remained.
Having finally recovered from a period of downsizing and uncertainty, Emily focused initially on rebuilding the teams.
Now, the common scenario in start-ups is that employees have to cover areas outside their imminent scope of work. Emily quickly realised that, due to the specific nature of their products, they also needed a dedicated customer support person to offload work from HR and Payroll. With that addition, things finally got moving again.
As the company scales, the CTO requires more concrete metrics to measure success. In Emily’s case, they’ve implemented a company scorecard to track key performance indicators (KPIs) and gain a clearer picture of the company’s health.
The key metrics they were monitoring at this stage were:
Of course, it took a while before they got in a position to actually measure success. It is just one of the realities of being a CTO in a scaling start-up. Security, data protection and onboarding new (big) customers were priorities. So at that point, measures of success were qualitative.
However, after implementing a company scorecard, they ended up with 15 metrics, measuring success and accountability weekly with a 13-week testing period.
Her immediate challenge was to define product metrics. One of them was the velocity measure. In Emily’s experience, this was the best place to start even though it’s not the best tool for measuring productivity.
The second one was the service-specific customer engagement metric; in other words, it is custom-made for the type of services Boundless is offering, and it should resolve the issue they had in the past where they didn’t really know if people were using people or products to solve the problem. Its purpose is, therefore, to measure the number of operations happening on a customer level while interacting with the product.
The final metric, this time from a project perspective, was customer incidents.
Besides measuring CSAT and NPS, Emily required insight into operational mistakes (eg, mistakes in payroll, a signed contract that has to be undone and redefined, bugs, etc.). The purpose was to immediately identify glitches in the system and improve the product/service.
You never know whether the thing that you’re about to measure is going to be right until you go and do it. — Emily Castles, Boundless CTO
As a scale-up CTO, you must always acknowledge the challenges of maintaining a culture of honesty and transparency as the company grows and the SLT becomes further removed from day-to-day operations. The emphasis must therefore be on open communication and public feedback channels to ensure visibility into potential issues. In practice, this means that if there’s a security incident (eg, breach) or anything like that, there should never be any kind of admonishment. You don’t want people sweeping problems under the carpet, after all, do you?
The immediate goal Emily is trying to achieve is eliminating the need to enter every information twice. Customers are putting a lot of data in their own systems, and then they have to put it into the Boundless systems as well. Granted, the company has various ways to pull data from one system to another but integrating with third-party HRIS systems seems like the best solution. So it has been a priority, but she’s struggled to identify the most critical problem to solve to decide which of the available solutions would be optimal.
Another thing she’s currently evaluating is whether to use a unified API or integrate directly with individual providers. After all, the company plans to grow and a unified API might impose certain limits.
Emily is also considering outsourcing some aspects of the project, but she wants to keep core development work in-house while allowing external developers to work on the edges of the project.
While operational expenditures haven’t been a major focus due to the company’s funding stage and relatively low operating costs, as the CTO, she is increasingly looking for ways to streamline internal operations and reduce the need for additional headcount.
As a part of that effort, she’s exploring no-code/low-code platforms like Retool and Microsoft Power Platform to build custom tools for internal teams.
Emily found the quarterly retrospectives with colleagues to be a valuable exercise, providing a structured opportunity for reflection and feedback. They also appreciated the external perspective and different language used in these sessions compared to internal meetings.
Looking ahead, she is focused on continuing to scale the company’s operations and product development efforts while maintaining a strong culture of transparency and collaboration. She is also excited to explore new technologies and approaches to streamline internal workflows and improve efficiency.
In the original shadowing session with Emily Castles, we explored the challenges and considerations of a CTO in a scaling start-up. It detailed topics such as:
As always during these sessions, attendees had the opportunity to ask questions and share knowledge and experience. So if you haven’t already, sign up for CTO Academy Membership to not only draw from the experience of seasoned technology leaders in different industries but to offer your own unique perspective.
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