Dermot Patrick O’Connor
Your Strategic Objective
Digital Execution Partner
The problem I solve.
I’m known as the “get it done” guy.
I help banking, fintech, consumer internet, and highly regulated firms build strategic execution capabilities that deliver predictably as they scale.
I bring 20+ years of experience leading strategic objective execution and organizational transformation for teams at Bitso and GBM in LATAM and BAT and GDS in London, redesigning product operating models during hyper-growth, reducing delivery lead times by 51%, improving critical customer workflows by 95%, and leading complex digital product execution serving millions of users.
I help organizations get back on track when they have identified a systemic inability to define and achieve strategic digital objectives.
If you have 3-4 quarters of missed deadlines, and leadership are looking for outside help to regain execution excellence, I can help.
Services
Explore the range of services designed to help you get your strategic outcomes back on track.
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Rapid diagnostic to identify and prioritize the digital objective that matters.
Review business & product objectives
Review performance data & known issues
Identify bottlenecks and gaps
Define the priority objective & key results
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End-to-end delivery of a single prioritized strategic digital objective.
Define the priority objective & key results
Design & deliver the solution with your team
Deliver and implement performance tracking
Full cross-functional stakeholder alignment
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Who it's for: CEOs, CPOs, and CTOs whose organization has strategic objectives on paper but no reliable mechanism to translate them into product and engineering execution — priorities shift quarter to quarter, objectives go undefined or unmeasured, and delivery drifts from what actually moves the business.
The problem it solves: The gap between strategy and execution has no owner. Leadership sets direction; product and engineering build things; nobody is accountable for the line connecting the two. That's how you end up with 3-4 quarters of missed objectives even when everyone's working hard.
What I do: I embed as a fractional execution partner at the leadership table — not just advising, but owning the mechanism that turns strategic objectives into a prioritized digital roadmap, and holding the org accountable to hitting it.
Deliverables:
Quarterly strategic objective and OKR framework, defined and facilitated end-to-end. Product/engineering roadmap derived from those objectives each cycle. A recurring cross-functional alignment cadence (leadership, product, engineering, ops). Monthly board/exec-ready reporting on objective progress, risk, and course-correction. Coaching for an internal lead to eventually own the cadence, so the org doesn't need me indefinitely.Timeline & format: Ongoing fractional retainer with quarterly renewal. Embedded roughly 10-12 hours/week or 40-50 hours/month, split between leadership cadence and hands-on execution oversight.
Recommendations
“We hired Dermot at a point in time when Bitso was growing at a speed seldom seen in the industry. We were assembling teams to launch products, countries, and even a new company.
This tremendous growth challenged our ability to execute, rendering our processes, structures, and documentation outdated almost as soon as they were implemented.
We needed someone with the skills and knowledge to look through the chaos and design, organize and execute the structures and processes that would help us scale our product processes.
Dermot did not disappoint. He deployed his wealth of knowledge to design organizational structures, such as new business tribes, and streamline product processes, including creating an entire process that went from ideation to execution, going through enterprise-level software architecture, redesigning roles, such as transitioning from the traditional PM/PO role divide to an SVPG PM role a la Marty Cagan. He demonstrated his deep understanding of what makes humans tick in an entrepreneurial environment by improving the morale of the team. This combination of skills also made him the ideal person to lead teams and teams of teams where needed, making sure they were shipping product and reaching business targets.
He quickly became a sought-after mentor for product managers, directors, and other leaders in the product and technology organization.
During his stay, Bitso grew 5x in size and 10x in valuation to become a double unicorn.
I would hire Dermot again if I had the chance.”
— Joel Salazar (Bitso)“After having worked closely with Dermot, I can confidently attest that he is a highly skilled leader who has the ability to inspire and guide any team to success. He combined his strategic vision with remarkable adaptability, effectively balancing immediate demands with long-term business objectives. Always radiating a positive attitude that was contagious and uplifting.
His pragmatic and problem-solving mindset, coupled with a commitment to continuous improvement, drove him to encourage us to shoot for the stars and trust our ideas. Simultaneously, he fostered a constructive environment where reflection on our proposals was encouraged, leading to enhanced decision-making for our next steps.
Furthermore, I want to emphasize Dermot's exceptional ability to foster collaboration, which distinguishes him as a leader who drives growth, not only within the company but also among his colleagues and team. Under his leadership, I experienced an enriching and motivating work environment.
It was an absolute pleasure working under Dermot's leadership, and I wholeheartedly recommend him for any opportunity that came his way.”
— Daniela Álvarez Ayala (Pulpo)“Dermot is an outstanding professional who consistently delivers exceptional work! His strong work ethic and dedication to excellence ensure that projects are not just completed, but completed successfully. Dermot has exceptional problem-solving abilities, and organizational skills. One of Dermot’s standout qualities is his helpful nature. He always went above and beyond to assist team members and stakeholders, offering guidance, support, and expertise whenever needed. Dermot is approachable and friendly, creating a positive work environment, fostering collaboration and open communication among team members. I learned a lot about project management, Jira, metrics and data analysis from Dermot. It was a such a pleasure working with him!”
— Louise Hannah (Globant\Indeed.com)