About CalypsoAI

CalypsoAI, established in 2018, is dedicated to securing the future of artificial intelligence by enabling enterprises to innovate confidently with cutting-edge security and compliance solutions. Our mission is to forge a secure path for safe AI adoption, empowering organisations to leverage AI technologies responsibly and without risk.

At CalypsoAI, we believe that securing the future of AI demands innovative thinkers from diverse disciplines and backgrounds. We are committed to building an elite team to advance groundbreaking technology and ensure businesses and society thrive with confidence.

Role Summary:

CalypsoAI is seeking a creative, analytical, and meticulous Prompt Engineer to join our dynamic team in Dublin. In this role, you will specialise in designing, refining, testing, and evaluating prompts to interact effectively and securely with Large Language Models (LLMs) and our cutting-edge agentic systems. Your expertise will be crucial in enhancing the capabilities of our AI security platform – contributing directly to our AI red-teaming tools and informing the design of robust AI defences.

Key Responsibilities:

Design, develop, and iterate on high-quality prompts for various LLMs and agentic systems to achieve specific goals related to AI security testing, red-teaming exercises (e.g., simulating prompt injection, jailbreaking, data elicitation), and defence validation
Analyse LLM outputs, identify failure modes or unexpected behaviours, and systematically refine prompts to improve performance, reliability, and safety
Develop and experiment with advanced prompting techniques (e.g., few-shot, chain-of-thought, structured prompting, role-playing) to maximise model capabilities relevant to security assessments
Collaborate closely with AI Researchers and Engineers to integrate effective prompts into CalypsoAI's security platform, red-teaming agents, and defensive solutions
Create and maintain a library of effective prompts, techniques, and best practices for internal use
Stay abreast of the latest developments in LLMs, prompt engineering methodologies, agentic AI frameworks, and AI security vulnerabilities
Document prompt design processes, experimental results, and performance evaluations clearly
Assist in evaluating the effectiveness and security implications of different prompting strategies

Required Qualifications:

Bachelor's degree in Computer Science, Data Science, Linguistics, Cognitive Science, Human-Computer Interaction, or a related field, OR equivalent significant practical experience in prompt engineering
Proven hands-on experience designing, testing, and refining prompts for large language models (e.g., GPT series, Claude, Llama, etc.)
Strong understanding of LLM capabilities, limitations, common failure modes, and alignment techniques
Familiarity with various prompt engineering techniques and strategies
Excellent analytical and problem-solving skills with meticulous attention to detail
Exceptional written and verbal communication skills
A keen interest in Artificial Intelligence, Natural Language Processing, and particularly AI Security.

Preferred Qualifications

Demonstrable experience applying prompt engineering, specifically within an AI security, red-teaming, or vulnerability testing context
Experience interacting with or developing for agentic AI systems or frameworks (e.g., LangChain, Auto-GPT concepts)
Basic scripting skills (e.g., Python) for prompt testing automation or analysis
Familiarity with methods for evaluating LLM performance and safety
Experience working with APIs for major LLM providers
A portfolio of examples showcasing creative and effective prompt engineering work
Understanding of adversarial attacks against NLP models

Life at CalypsoAI

At CalypsoAI, we believe that our people are the driving force behind our success. We foster a dynamic, collaborative, and inclusive work environment where innovation thrives, and employees feel empowered to make a real impact. Whether you’re working remotely or at one of our offices, we ensure you have the tools, flexibility, and support to do your best work.

Location

Work on a hybrid schedule:

Dublin Office: Thursdays
Remotely or Dublin Office: Monday, Tuesday, Wednesday and Friday

Our Benefits & Perks

We offer a competitive benefits package designed to support your well-being, growth, and work-life balance:

✅ 25 Days Annual Leave – We believe in the importance of rest and recharge. Enjoy generous time off to relax and pursue personal passions.

✅ Fully Covered Health & Dental Insurance – Your well-being is our priority. We provide comprehensive health and dental coverage to keep you and your family protected.

✅ Pension Plan (Up to 3% Employer Match) – We invest in your future with a competitive pension plan, matching contributions up to 3%.

✅ TaxSaver & Bike to Work Scheme – Save on commuting costs with our tax-efficient travel benefits, whether you prefer public transport or cycling.

✅ Income Protection – We offer financial security and peace of mind in the event of unforeseen circumstances.

✅ Hybrid Working – We embrace flexibility, offering a hybrid work model that allows you to balance in-office collaboration with remote work.

✅ Dublin City Centre Office – Our modern, conveniently located office in the heart of Dublin provides an inspiring space for collaboration and connection.

✅ Catered Lunch Twice a Week – For those working from the office, we provide delicious, catered lunches twice a week to fuel your productivity and connection with colleagues.

✅ Quarterly Social Events – We love bringing our teams together! From team outings to special events, we ensure there are plenty of opportunities to connect and have fun.

✅ Annual CalypsoAI Day – Each year, we dedicate a special volunteering day for employees to contribute to causes that matter.

✅ Learning & Development Platforms – We support continuous growth with access to online learning platforms, helping employees upskill and stay ahead in their careers.

✅ Work from Anywhere (Up to 3 Weeks Per Year) – Enjoy the freedom to work from anywhere in the world for up to three weeks each year.

✅ Increased Benefits with Tenure – At CalypsoAI, we recognise and reward long-term dedication. As you grow with us, you'll enjoy enhanced pension contributions and additional annual leave, ensuring your commitment is recognised and supported.

At CalypsoAI, you’ll be part of an ambitious, fast-growing team shaping the future of AI security. If you're looking for a role where you can make an impact while enjoying a supportive and rewarding work environment, we’d love to hear from you!

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