Chief Technology Officer (CTO)

This role is part of our AddSearchteam, 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 OverviewWe'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 responsibilitiesTechnical LeadershipDefine and drive technical architecture for both our mature search platform and evolving RAG solutionMake critical technical decisions on scaling, infrastructure, and product evolutionSolve difficult technical problems that the team escalatesGuide technology choices and evaluate new tools/approaches (especially AI-assisted development)Own deployment strategy, operational readiness, and infrastructure reliability across all engineering initiatives.Team & PeopleLead and mentor a team of 6 experienced engineers (5 developers + 1 solutions engineer)Foster a culture of technical excellence, autonomy, and continuous learningConduct code/design reviews and provide thoughtful technical feedbackAct as a coach rather than commander - this team values collaborationBusiness & OperationsReview and assess technical requirements in enterprise contractsHandle security questionnaires and compliance requirements (SOC2, GDPR, etc.)Lead our SOC 2 compliance / auditsCollaborate with CEO, product, sales and marketing leadership on product roadmapBalance technical debt, feature development, and operational stabilityHands-On ContributionContribute 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 applicationsChampion modern development practices (we use AI-assisted tools like Claude Code, Codex)What You bring to the tableMust-haves:10+ years of software engineering experience, with significant time in technical leadership rolesStrong 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, AWSExperience with AI/ML systems, particularly RAG architectures, LLMs, and prompt engineeringTrack record leading senior engineering teams (not necessarily large teams, but experienced ones)Comfort with enterprise B2B dynamics: contracts, SLAs, security reviews, complianceAmbition and curiosity around product direction and customer problems, not just technical implementationExcellent English communication (written and verbal)Nice-to-haves:Prior CTO or VP Engineering experienceExperience with: Dropwizard, FastAPI, MySQL, OpenSearch/Elasticsearch, Terraform/PulumiFamiliarity with LangChain/LangSmith/LangFuse or similar observability/eval toolsBackground in search, information retrieval, or adjacent domainsExperience scaling products from early traction to enterprise maturityWhat won't work:Pure "ivory tower" architects who can't get into technical detailsHeavy top-down management styles (this team values autonomy)No exposure to modern AI/LLM developmentOur StackBackend: Java (Dropwizard), Kotlin, Python (FastAPI)Data: MySQL, OpenSearchAI/RAG: Python, LangFuse, LangSmith for evalsInfrastructure: AWS (manual + Terraform + Pulumi)Development: Claude Code, Codex, modern AI-assisted workflowsApproach: Experimenting with prompt-based and script-driven software factory patternsWhat’s in it for YouUltimate 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