• Architect and build the company’s initial product and technical foundation • Design reliable systems for high-trust operational workflows • Lead technical direction across infrastructure, AI systems, and application architecture • Work directly with design partners to shape product direction and workflow design • Establish engineering standards around reliability, auditability, and explainability • Recruit and lead the founding engineering team • Partner directly with the CEO on fundraising and company strategy

• Architect and build the company’s initial product and technical foundation • Design reliable systems for high-trust operational workflows • Lead technical direction across infrastructure, AI systems, and application architecture • Work directly with design partners to shape product direction and workflow design • Establish engineering standards around reliability, auditability, and explainability • Recruit and lead the founding engineering team • Partner directly with the CEO on fundraising and company strategy

Role Description We are recruiting a dedicated fractional CISO for our Winchester, Virginia-based client, who delivers the security program for a regional CPA firm of about 350 people. This is not a portfolio role. All hours go to the single CPA firm engagement, and the hire owns the firm's information security program end-to-end. The CPA firm's internal IT team handles day-to-day operations. Our Winchester, Virginia-based client owns security on the firm's behalf, and the hire is the senior face of that program. The CPA firm values continuity and a close advisory relationship with their CISO, so this role suits someone who wants to go deep with one organization rather than rotate across many. - Own the CPA firm's information security strategy, roadmap, governance, and executive reporting - Maintain and mature the firm's GLBA / FTC Safeguards Rule and HIPAA compliance posture - Serve as the executive-level security voice to the CIO, CTIO, managing partners, and audit/risk committee - Lead policy development, risk assessment, third-party risk, and incident response governance - Provide principal-level technical advisory on architecture, tooling, and cloud security decisions — security and adjacent technology - Partner with the delivery teams of our Winchester, Virginia-based client on tactical execution (pentest scoping, VM strategy, security tooling rollouts) - Brief the CPA firm's leadership quarterly and on-demand for major events Qualifications - 7+ years in information security leadership, including 3+ in a CISO, vCISO, or Director of Security capacity - Direct experience supporting CPA firms or comparable professional services environments - Working command of GLBA / FTC Safeguards Rule and HIPAA — applied, not just templated - Strong technical foundation: substantive engagement on cloud (Microsoft / Azure preferred), endpoint security, network security, and identity - Executive presence — able to sit across from a managing partner and earn their trust quickly - Willing and able to act as a principal technology advisor on decisions that extend beyond strict security scope Preferred Experience - Active CISSP, CISM, or CCISO - Prior in-house experience inside a public accounting firm's IT or risk organization - Familiarity with SOC 2 and PCI in adjacent contexts Compensation - $100–$125/hour, 1099 contractor - Approximately 20 hours per month, with rare months extending toward 40

Role Description Development and infrastructure projects operate through fragmented workflows involving multiple stakeholders, consultants, agencies, and approval bodies. Critical issues often surface late, coordination across teams breaks down, and experienced project managers become the operational bottleneck. Most software in this category focuses on task tracking or document management. We believe the next generation of platforms will instead structure decision-making, verification, and submission readiness across complex operational workflows. We are building toward that future. This is an opportunity to help define a new category at the intersection of applied AI, operational systems, and high-trust workflows. Landera is building workflow intelligence software for development and infrastructure teams managing complex approval and coordination processes. The focus is not generic automation. The focus is on helping teams: - Surface risk earlier - Improve coordination across stakeholders - Structure high-friction workflows - Increase operational throughput without increasing risk We are approaching this as a systems problem first, not a feature problem. The company is currently in formation with active design partners, validated customer demand, and strong early market feedback. The CEO co-founder is already in place and has completed extensive customer discovery across development, planning, and infrastructure workflows. We are looking for a technical co-founder who wants to help shape both: - The product vision - The underlying technical architecture This is not a traditional CTO hire. You will operate as a true founder with meaningful ownership, strategic influence, and responsibility across: - Product - Engineering - Hiring - Fundraising - Company direction Qualifications - Has experience shipping production-grade software systems in environments where outputs carried operational or business consequences - Has strong technical judgment across modern AI systems, data pipelines, workflow software, and secure SaaS architecture - Understands the tradeoffs between automation, reliability, and human oversight - Enjoys solving ambiguous systems problems with high ownership - Wants to build as a founder, not operate as an employee Requirements - Prior startup or founder experience - Experience in PropTech, AEC, GovTech, legal tech, fintech, or other high-trust workflow domains - Experience building systems involving document understanding, workflow orchestration, or operational intelligence Benefits - This is an opportunity to build one from the ground up. How to Apply Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate. FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.