CTO - Enterprise Search and AI/RAG Solutions

This role is part of our AddSearch team, one of our growing brands at saas.group.

AddSearch is a ~15-person B2B SaaS company providing enterprise site search and content discovery solutions to mid-sized to large customers with demanding compliance, custom contract, and SLA requirements. Our core product is mature and stable, while our newest offering - an AI-powered RAG solution - is driving the majority of our current sales growth.

Profile Overview

We're looking for a hands-on CTO to lead our technical strategy and a senior team of 5 engineers plus a solutions engineer. This is a player-coach role: you'll set architectural direction, solve complex technical problems, and support the team's growth-while remaining close enough to the code to earn the team's respect.

You'll be joining a company at an inflection point: maintaining a stable, high-SLA enterprise product while scaling a newer AI/RAG solution. You'll need to balance both.

Why join now? This is a rare opportunity to lead technical strategy at a company with a stable, profitable core and genuine AI-driven growth momentum. It’s not a pivot, but a second act built on solid foundations. You'll work with a highly experienced, autonomous team that doesn't need hand-holding, in a fully remote culture built around trust and outcomes. As the person shaping both our legacy platform and our emerging AI products, you'll collaborate directly with the CEO and executive peers. Your technical decisions will have real business weight from day one.

Your responsibilities

Technical Leadership

• Define and drive technical architecture for both our mature search platform and evolving RAG solution
• Make critical technical decisions on scaling, infrastructure, and product evolution
• Solve difficult technical problems that the team escalates
• Guide technology choices and evaluate new tools/approaches (especially AI-assisted development)
• Own deployment strategy, operational readiness, and infrastructure reliability across all engineering initiatives.

Team & People

• Lead and mentor a team of 6 experienced engineers (5 developers + 1 solutions engineer)
• Foster a culture of technical excellence, autonomy, and continuous learning
• Conduct code/design reviews and provide thoughtful technical feedback
• Act as a coach rather than commander - this team values collaboration

Business & Operations

• Review and assess technical requirements in enterprise contracts
• Handle security questionnaires and compliance requirements (SOC2, GDPR, etc.)
• Lead our SOC 2 compliance / audits
• Collaborate with CEO, product, sales and marketing leadership on product roadmap
• Balance technical debt, feature development, and operational stability

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Hands-On Contribution

• Contribute to architecture and design (you don't need to write code daily, but you should be able to)
• Stay current with AI/ML developments, especially in RAG and LLM applications
• Champion modern development practices (we use AI-assisted tools like Claude Code, Codex)

What You bring to the table

Must-haves:

• 10+ years of software engineering experience, with significant time in technical leadership roles
• Strong hands-on experience with AI-assisted development tooling (e.g., Claude Code, Cursor, Copilot)
• Working knowledge of our stack or ability to quickly ramp: Java/Kotlin, Python, AWS
• Experience with AI/ML systems, particularly RAG architectures, LLMs, and prompt engineering
• Track record leading senior engineering teams (not necessarily large teams, but experienced ones)
• Comfort with enterprise B2B dynamics: contracts, SLAs, security reviews, compliance
• Ambition and curiosity around product direction and customer problems, not just technical implementation
• Excellent English communication (written and verbal)

Nice-to-haves:

• Prior CTO or VP Engineering experience
• Experience with: Dropwizard, FastAPI, MySQL, OpenSearch/Elasticsearch, Terraform/Pulumi
• Familiarity with LangChain/LangSmith/LangFuse or similar observability/eval tools
• Background in search, information retrieval, or adjacent domains
• Experience scaling products from early traction to enterprise maturity

What won't work:

• Pure "ivory tower" architects who can't get into technical details
• Heavy top-down management styles (this team values autonomy)
• No exposure to modern AI/LLM development

Our Stack

• Backend: Java (Dropwizard), Kotlin, Python (FastAPI)
• Data: MySQL, OpenSearch
• AI/RAG: Python, LangFuse, LangSmith for evals
• Infrastructure: AWS (manual + Terraform + Pulumi)
• Development: Claude Code, Codex, modern AI-assisted workflows
• Approach: Experimenting with prompt-based and script-driven software factory patterns

What’s in it for You

• Ultimate flexibility: We’re 100% remote. You can work from any European Union country.
• Freedom and autonomy: We’re a high-trust team, and you’ll be given lots of flexibility to solve problems in your own way, with plenty of help from the team when you need it.
• Minimum bureaucracy: We don’t like to get bogged down with meetings and red tape. We like to be efficient and keep momentum steady & sustainable.
• Small & friendly team: We help each other out, have fun, and joke around.
• Our network: We are a community of entrepreneurial SaaS professionals that regularly exchange ideas, knowledge, learning and expertise with each other internally.
• Flexible time off: We want you to recharge your batteries when needed.

AddSearch is part of saas.group and we have a shared goal of succeeding together.

What is saas.group?

Think of us as the driving catalyst behind your favorite software success stories. saas.group, established in 2017, is on a mission to turbocharge promising B2B SaaS ventures, unlocking their full potential. As a Software-as-a-Service portfolio powerhouse, we specialize in acquiring small software treasures and polishing them into industry stars. With a dynamic, fully remote team of nearly 380+ colleagues spanning 50+ countries we are truly global and we are rewriting the playbook on SaaS innovation and collaboration. We grow 25 exciting brands under our umbrella. Feel free to explore our Candidate's Hub to get an insider's view, dive into our culture, gain valuable insights into our teams and how we work.

Also, don’t forget to follow saas.group on LinkedIn to stay up-to-date on our job openings, podcast episodes, and with all things happening at our company.

We don’t just simply offer you to “take a job with us” but rather to “join us on this journey” to build the world's largest platform of independent SaaS companies.

Sounds like something you’re up for? Feel free to apply even if you don’t check all these boxes. We believe in the power of diversity and fresh perspectives to spice up our team. Your application might just be the missing ingredient!

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saas.group is committed to creating a diverse and inclusive workplace. We are proud to be an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you're passionate about working with a team that values innovation, excellence, and fairness, we encourage you to apply.