At CloudsineAI

CloudsineAI builds AI agent security and governance software. Founded in Singapore in 2012, we protect over 12,000 web properties for customers across five countries, and our platform secures LLM and agentic applications inside some of the region's most tightly regulated environments - including a large Singapore government agency running up to 100 public-facing LLM applications. We are the sovereign AI-agent security platform for regulated Asia-Pacific.

TraceCtrl, our agentic AI governance platform, is where we are placing our weight. Deals like these are won or lost in the technical room: buyers in government, defence and financial services do not buy from a slide - they buy after an evaluation, run in their own environment, against their own constraints. This role owns that room, paired with enterprise sales.

What this role does

You are the technical owner of a TraceCtrl opportunity from first discovery call through to a completed evaluation. You work directly alongside the Chief Commercial Officer and our enterprise sales motion on high-value, high-touch deals.

TraceCtrl is the priority and the clear majority of this role. You will occasionally support evaluations across the rest of our portfolio - web security and monitoring - where the technical question overlaps.

Two things you own, and one you contribute to.

You own: technical discovery and solution design

Run discovery with security architects, platform teams and CISOs - surface the real constraints before anyone proposes anything: data residency, egress restrictions, model hosting, identity, and the SIEM or SOC tooling already in place.
Design the deployment. SaaS, customer VPC or private cloud, on-premise virtual machines, containerised platforms such as Kubernetes and OpenShift, and fully air-gapped environments where licensing, model updates and telemetry all behave differently.
Translate constraints into scoped solution options, and write the technical sections of proposals, RFP and tender responses.

You own: demonstrations, POCs and evaluations

Take proof-of-concept and pilot engagements end to end: scope, success criteria, environment build, execution, and the readout that closes or kills the deal.
Define what gets measured - and, just as importantly, what is explicitly out of scope - so an evaluation is scored on the things our product actually determines.
Run competitive bake-offs, including adversarial and red-team style testing against LLM and agentic applications.
Handle the objection you cannot deflect: false positives, latency, integration effort, sovereignty. Answer it with evidence, not assertion.

You contribute to: the product feedback loop

Carry structured field requirements back to product and engineering - what customers actually asked for, how often, and what it cost us when we could not deliver it. This is a standing input to the roadmap, not a documentation workstream. Narrative, positioning and technical content sit with our technical product manager you are not being hired to write them.

Throughline KPI: evaluations entered are evaluations won

Everything above serves one outcome: TraceCtrl evaluations we enter, we win - and faster than we do today.

90-day success in this role looks like:

A meaningful number of TraceCtrl evaluations advanced alongside enterprise sales, with you as the technical lead.
Time from first technical conversation to evaluation sign-off measurably shorter than it is today.
Product engineers no longer pulled into routine customer calls, because you are handling them.

What you bring

Must-haves

5-8 years in solutions engineering, pre-sales, technical consulting or security architecture - with enterprise or public-sector buyers, not SMB self-serve.
Two to three years hands-on with LLM or agentic systems. You have built, deployed, integrated or secured them yourself. Reading about them does not count.
Real fluency across deployment models: SaaS, private cloud, on-premise, containerised and air-gapped - including what breaks in each. Comfort with identity and SSO integration, network segmentation, and agent- or endpoint-based deployment across distributed estates.
A working security foundation: common attack classes, application security, and how a security team actually operates day to day.
The ability to lead a technical room. Our buyers are sceptical by profession and will aim their hardest questions at you. You set the direction of that conversation - with our CEO, product management and security research colleagues to draw in when a question genuinely needs them.
Clear written English. A large share of this role is scoping documents and evaluation readouts that a procurement officer will read without you there to explain them.

Application bar

In your cover note, walk us through one technical evaluation or POC you personally scoped and ran - the environment and its constraints, the objections you hit, what you changed mid-flight, and how it ended. We are equally interested in one you lost. How you describe a loss tells us more than any certification.

Nice-to-haves

Experience selling into Singapore government or financial services, and familiarity with how those procurement cycles actually run.
Working knowledge of AI security frameworks - OWASP Top 10 for LLM Applications, MITRE ATLAS, NIST AI RMF - or of MAS guidance on AI risk.
Background in web security, WAF, or website monitoring and defacement protection.
Security certifications (CISSP, OSCP, cloud security specialisations) are welcome but will not substitute for the application bar above.

How we work

We are a small Singapore-based team with a long operating history and a deliberately short decision chain. This role reports to the Chief Commercial Officer and works daily with product and engineering. You will have direct access to the people who build the product, and your field input will change what gets built.

The work is hybrid, based in Singapore, with regular time on customer sites. Some engagements are in secure or restricted environments, which carry their own access and clearance requirements.

TraceCtrl is early and moving quickly. If you need a settled product and a mature playbook, this will frustrate you. If you would rather be the person the room turns to, this is the seat.

Compensation is base plus variable, with equity participation.

AI Cyber Solutions Engineer