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Hi, I’m Richard Stevens Ashford, a seasoned engineering leader with over 15 years of experience building and scaling cross-functional teams to deliver innovative software products. I thrive on turning ambitious ideas into robust platforms, nurturing high-performing cultures, and partnering with product, data, and security teams to align technology with business goals. As a leader who values practical architecture, security, and data-driven decision-making, I’ve led international scale-ups, driven PCI-DSS compliance, implemented trunk-based CI/CD, and created scalable QA and data pipelines. I enjoy mentoring engineers, hiring talent, and enabling teams to move fast responsibly while delivering measurable impact.…Hi, I’m Richard Stevens Ashford, a seasoned engineering leader with over 15 years of experience building and scaling cross-functional teams to deliver innovative software products. I thrive on turning ambitious ideas into robust platforms, nurturing high-performing cultures, and partnering with product, data, and security teams to align technology with business goals. As a leader who values practical architecture, security, and data-driven decision-making, I’ve led international scale-ups, driven PCI-DSS compliance, implemented trunk-based CI/CD, and created scalable QA and data pipelines. I enjoy mentoring engineers, hiring talent, and enabling teams to move fast responsibly while delivering measurable impact.

Richard Stevens

Full Stack Developer, Back-End Developer, Cloud Developer, +3

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Hi, I’m Richard Stevens Ashford, a seasoned engineering leader with over 15 years of experience building and scaling cross-functional teams to deliver innovative software products. I thrive on turning ambitious ideas into robust platforms, nurturing high-performing cultures, and partnering with product, data, and security teams to align technology with business goals. As a leader who values practical architecture, security, and data-driven decision-making, I’ve led international scale-ups, driven PCI-DSS compliance, implemented trunk-based CI/CD, and created scalable QA and data pipelines. I enjoy mentoring engineers, hiring talent, and enabling teams to move fast responsibly while delivering measurable impact.…Hi, I’m Richard Stevens Ashford, a seasoned engineering leader with over 15 years of experience building and scaling cross-functional teams to deliver innovative software products. I thrive on turning ambitious ideas into robust platforms, nurturing high-performing cultures, and partnering with product, data, and security teams to align technology with business goals. As a leader who values practical architecture, security, and data-driven decision-making, I’ve led international scale-ups, driven PCI-DSS compliance, implemented trunk-based CI/CD, and created scalable QA and data pipelines. I enjoy mentoring engineers, hiring talent, and enabling teams to move fast responsibly while delivering measurable impact.

Available to hire

Hi, I’m Richard Stevens Ashford, a seasoned engineering leader with over 15 years of experience building and scaling cross-functional teams to deliver innovative software products. I thrive on turning ambitious ideas into robust platforms, nurturing high-performing cultures, and partnering with product, data, and security teams to align technology with business goals.

As a leader who values practical architecture, security, and data-driven decision-making, I’ve led international scale-ups, driven PCI-DSS compliance, implemented trunk-based CI/CD, and created scalable QA and data pipelines. I enjoy mentoring engineers, hiring talent, and enabling teams to move fast responsibly while delivering measurable impact.

Skills

Experience Level

Expert

Expert

Expert

Expert

Expert

Expert

Expert

Expert

Expert

Expert

Language

English

Fluent

Work Experience

VP of Engineering / CTO at Fedr/Caterdesk

September 1, 2020 - November 15, 2025

Provided senior leadership across product, engineering, QA, and data functions; drove cross-functional alignment across EU and AU operations; expanded teams from a small squad to ~25 engineers and managers; defined technical strategy, OKRs, and delivery standards.

Consultant at Rumage

December 1, 2020 - December 1, 2020

Early-stage tech advisor for a funded startup; built MVP systems enabling funding, scale preparation, and partner integration; recommended CI/CD scaling, onboarding of external vendors, and scalable architecture to support next funding round.

Tech Lead at Holiday Extras

September 1, 2020 - September 1, 2020

Scaled engineering from 6 to 400+ engineers, QA, and managers; led cross-functional direction, architecture, and rollout across multiple sites; established scalable QA processes, onboarding, and a data-driven product development approach; drove PCI-DSS compliance and security controls; transitioned to more agile, trunk-based development and multi-daily deployments.

VP of Engineering / CTO at Feedr/Caterdesk

September 1, 2020 - November 15, 2025

Senior engineering leadership across product, engineering, QA, and data functions; scaled cross-EU/ AU teams post-acquisition; defined org-wide technical strategy, OKRs, and delivery standards. Built AI-powered quoting and sales automation using LLMs and ML models to streamline processes for caterers, improving conversion and operational efficiency. Achieved PCI-DSS compliance with zero critical/high-risk findings and implemented end-to-end security controls and cloud best practices. Accelerated delivery velocity by migrating to trunk-based development and enabling multiple daily deployments. Transformed product and data functions with centralized analytics, ETL, and customer-centric discovery practices. Drove international expansion, scalable infrastructure, and cross-functional alignment; established OKRs and roadmaps for eng, product, and QA; optimized cross-team collaboration and modern tooling for continuous delivery.

Head of Engineering / Head of Architecture / Head of Data at Holiday Extras

September 1, 2020 - September 1, 2020

Scaled engineering, QA, and data organizations from a small team to 400+ engineers and managers across multiple sites. Led global teams, established shared architecture, practices, and delivery standards, and aligned cross-organization goals. Built and matured architecture for CMS, search, flight tracking systems, live pricing, and broader infrastructure still in use today. Implemented a scalable static flight service reaching millions of flights globally and reduced cycle times by introducing trunk-based development, modern CI/CD, and on-boarding automation. Recruited, mentored, and grew engineering talent; defined product roadmaps and OKRs; fostered a high-performance, customer-focused culture. Drove security, compliance (PCI-DSS), and cross-functional collaboration; established cross-team governance and architecture to support international growth and remote work.