Co-founder – Chief Technology Officer, AI ROI Measurement Platform

FutureSight

Co-founder role in an AI ROI measurement platform, setting architecture and leading engineering team. Engaging with C-level executives and shaping technical agenda.

Posted 5/5/2026full-timeRemote • 🇨🇦 CanadaLeadWebsite

About the role

Key responsibilities & impact

You will write the first lines of production code.
You will set the architecture, the data model, the engineering culture, and the security posture.
You will represent the company in front of CIOs, Chief AI Officers, CFOs, security teams, and investors.
You will recruit and lead the founding engineering and applied AI team.
Months 0–3. Ship the discovery layer with a design partner — browser extension and endpoint agent capturing AI usage across ChatGPT, Claude, Gemini, Copilot, and the long tail without per-vendor integrations. Establish the core architecture and 15-minute refresh pipeline.
Months 3–6. Deliver the Utilization × Proficiency × Value framework, including the first GitHub/Jira correlation for engineering ROI. Convert three paid pilots. Begin SOC 2 Type II readiness with zero-content-retention as a non-negotiable design constraint.
Months 6–9. Release GA v1 covering discovery, analytics, proficiency benchmarking, and governance controls aligned to EU AI Act, ISO 42001, and NIST AI RMF. Convert pilots to ten paying enterprise customers. Finalize pricing — including outcome-based pricing on captured savings.
Months 9–18. Ship the governed AI access hub and expand into a vertical specialization — most likely an autonomous AI FinOps agent for a regulated industry — that no horizontal incumbent can credibly follow. Reach $1M ARR. Build out the founding team.

Requirements

What you’ll need

You have shipped data-intensive, multi-tenant SaaS into enterprise production, with buyers including CIOs, CFOs, and CISOs.
You hold the full stack confidently: browser extensions and endpoint agents, high-throughput event ingestion, real-time analytics pipelines, applied LLMs and prompt-quality evaluation, and the demands of secure multi-tenant SaaS (SOC 2, tenant isolation, audit logging, data residency).
You have well-formed convictions about telemetry design, privacy-preserving instrumentation, and the line between observation and surveillance — developed through production experience, not from reading about it.
You favour systems that perform consistently across heterogeneous enterprise environments over systems that demonstrate well in controlled settings.
You are prepared to operate as a principal — setting the technical agenda, making decisive calls in uncertain conditions, and owning the outcomes.
Strongly preferred
Prior founder, or early-stage technical leadership experience.
Background in enterprise observability, FinOps, security analytics, or governance/GRC platforms — categories where the buyer expects auditable evidence, not narrative.
Direct experience shipping browser extensions or endpoint agents at enterprise scale.
Applied LLM evaluation experience: prompt-quality scoring, output benchmarking, or model-routing systems, including the cost, quality, and privacy trade-offs of self-hosting foundation models.

Benefits

Comp & perks

Founder-level equity. A meaningful ownership stake, structured for long-term value creation and aligned across funding rounds.
Founder-level authority. Co-decision rights on product, technology, hiring, fundraising, and strategy. A board or board-observer seat, as appropriate to the cap table and stage.
A committed partner, FutureSight co-founding team.
Pre-seed capital. FutureSight invests directly in the venture at pre-seed

ATS Keywords

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Hard Skills & Tools

production codedata modelarchitecturebrowser extensionsendpoint agentsevent ingestionreal-time analyticsapplied LLMsSOC 2telemetry design

Soft Skills

leadershipdecision makingtechnical agenda settingoperational readinessconviction in design

Certifications

SOC 2 Type II