Chief Technology Officer in California, Maryland at CIRE INVESTMENT SERVICES

CIRE Equity is a privately held, vertically integrated real estate investment firm focused on creating and preserving long-term value through targeted investments in commercial real estate across the Western United States. We take a disciplined, hands-on approach to investing, combining thoughtful analysis with active execution to responsibly grow investor capital while protecting it over time.

How we work matters just as much as what we invest in. At CIRE, we operate in a collaborative, hands-on environment where people are encouraged to take ownership, ask thoughtful questions, and respect one another. We believe consistent, high-quality work and a willingness to keep getting better drives meaningful growth for our investors, our team, and the communities where we invest.

We do our best work when people are aligned around a shared purpose. Our success, individually and as a team, comes from a clear vision and a set of core values that guide how we make decisions, work together, and build for the long term. These values aren’t aspirational; they’re part of our cultural DNA and the standards we hold ourselves to every day.

Fiduciary First

Stewardship for all our stakeholders

Create Opportunity

Where others see limits, we see launchpads

Intentional Evolution

“Learn-it-alls,” not “know-it-alls”

Authentic Relationships

Care deeply, connect genuinely

Effective Performance

Results with purpose

Beyond technical skills, we look for people with strong emotional intelligence, self-awareness, and a genuine commitment to winning together. Open dialogue, direct feedback, and psychological safety are core to how we work and are essential to building strong teams and achieving better outcomes, especially in complex, fast-moving environments. We work hard, support one another, and take pride in what we build collectively, measuring success not just by results, but by the strength of the team behind them.

CIRE Equity is seeking a CTO to serve as the senior technical authority the organization requires for growth. This is a full-time, Executive Leadership Team (ELT)-level position. It is a strategic leadership function — one that owns the technology and data direction of a $1B+ AUM commercial real estate private equity firm with high growth targets and translates that direction into a roadmap the internal team can execute against.

The role is designed for a leader who operates with hands-on technical conviction: someone whose opinions on AI, data architecture, and platform decisions are grounded in active practice, not delegation. The CTO contributes a technical lens to firm-level strategy for a team that is forward thinking about technology. We are targeting a builder from a product company who can both set technical direction and execute hands-on.

AI, Automations, & Data Strategy

• Serve as the technical authority on AI initiatives, stress-testing the roadmap, prioritizing initiatives, architecture decisions, build vs. buy calls, execution grounded in sound engineering judgment
• Review and refine data architecture standards across core systems (MRI, Argus, Microsoft) and oversee data warehouse initiatives to serve long-term reporting and analytics needs across the organization
• Define how data flows between platforms and where it lives authoritatively
• Work across functions to understand business needs and oversee workflow automation by internal and external parties

Product & Technology Decisions

• Lead major product evaluations and recommend integration decisions for executive approval
• Lead the build of custom, line-of-business applications and products to align with corporate strategy and goals
• Establish a technology governance model and policies
• How decisions get made, documented, and enforced, including approval thresholds and escalation structure
• Structure for evaluating new technologies and contracting protocol
• Data access controls, acceptable use, vendor risk, PII protection
• Establish ROI measures and success metrics for technology implementations
• Define technical standards the internal team operates within
• Holds authority to reverse or redirect prior technology decisions where necessary to execute the roadmap
• Own the technology budget and vendor contract negotiations, ensuring spend aligns with ROI and strategic priorities
• Establish a build-vs-buy framework for evaluating internal development against third-party and vendor solutions
• Partner with department leads to identify workflow gaps addressable through custom tooling or automation

Cybersecurity

• Own and continuously strengthen the firm's cybersecurity posture, directing controls to identify exposure gaps, advise on third-party risk, and ensure the firm's security practices keep pace with its technology footprint
• Coordinate with Legal on incident response planning and breach notification readiness
• Own SOC 2 readiness and the compliance roadmap where applicable to support investor and institutional diligence
• Set data access and identity management standards across all systems
• Report cybersecurity posture and key risk indicators to the leadership team on a regular cadence

Technology Roadmap

• Translate business strategy into a sequenced, achievable technology roadmap
• Make recommendations on internal and external resources to ensure the organization is equipped to achieve its technology goals
• Balance quick wins against long-cycle infrastructure investments
• Provide technical perspective in decision making to ensure both business and technical facts are weighed appropriately
• Report to COO on roadmap progress, risks, and resource gaps

Cross-Functional Leadership

• Serve as the senior technical voice in cross-departmental decisions
• Mentor and advise internal technology staff on technical direction and professional development
• Bridge the gap between business stakeholders and technical execution

• Position reports directly to: Co-Founder & Principal, Trevor Smith

• Senior and technically credible — opinions backed by hands-on practice, not abstraction
• Hands-on with AI/ML tooling, data architecture, and modern SaaS integration patterns
• High EQ to operate inside a firm with established leaders and existing team dynamics
• Comfortable owning a roadmap with real accountability, not advisory influence
• Experience in B2B, ERP, or regulated-data environments strongly preferred, with demonstrated ability to navigate complex business structures beyond consumer-facing technology
• West Coast preferred but not required. Willingness and ability to travel to Southern California quarterly to attend in-person executive meetings.

• 10+ years of technology leadership experience, including CTO, VP of Engineering, or equivalent senior roles
• Background as a builder at a product company, shipping software as CTO or VP of Engineering rather than a consulting, systems-integrator, or infrastructure-only track record
• Demonstrated track record building and executing technology roadmaps in mid-market or growing firms
• Demonstrated track record for building high-performing teams
• Active AI/ML practitioner — not just strategic familiarity; hands-on with current tooling
• Deep experience with SaaS platform integrations, data architecture, and API-connected ecosystems
• Prior experience in commercial real estate, proptech, or financial services, or other industries with complex data environments strongly preferred
• Familiarity with data privacy and security frameworks relevant to investor data, including CCPA, SEC safeguarding requirements, and state breach notification laws, with SOC 2 familiarity
• Proven ability to operate effectively in a principal-led, entrepreneurial firm where trust is earned through results

This is a remote, full-time employee position. The primary working environment will be virtual, with periodic on-site visits to CIRE Equity’s offices for strategic planning sessions, team alignment meetings, and key presentations. The CTO is expected to maintain a professional remote setup suitable for video conferencing and collaboration.

Periodic travel to CIRE’s primary office and asset locations may be required. Estimated frequency is 1–3 times per year, depending on roadmap milestones and strategic priorities.

The physical demands of this position are consistent with professional knowledge work conducted in an office or home-office setting. Primary activities include extended computer use, video conferencing, and document review. No significant physical requirements are associated with this role beyond standard office conditions.