Chief Technology Officer (CTO) / Lead Software Architect

Job Title: Chief Technology Officer (CTO) / Lead Software Architect

Company: Confidential Client (AI Automation Platform for Commercial Real Estate)

Represented by: Mako Professionals - Enterprise IT & AI Staffing Experts

Location: Remote (Founder in NYC, Investors in Florida)

Engagement Type: Full-time or 1099 Contract

Compensation: $140K $200K base competitive equity package

About the Company: Join an innovative AI-driven technology startup reshaping the commercial real estate industry with a next-generation automation platform. This cutting-edge solution automates underwriting, loan servicing, and asset management processes, transforming complex documents into enriched, standardized reports seamlessly integrated with Microsoft Office tools like Excel, Word, and PowerPoint. As the company gears up for its next phase of growth-transitioning from a desktop-based .NET solution to a scalable, cloud-native SaaS product-your expertise will guide the technical evolution.

Position Overview: Mako Professionals is on a mission to find a dynamic and visionary CTO / Lead Software Architect to helm the technical journey at this pioneering startup. This role is perfect for a seasoned professional ready to take a hands-on approach in coding, system design, and team leadership to elevate a working prototype to an enterprise-ready solution. You'll be instrumental in defining the technical roadmap, steering a small but talented team of developers, and collaborating closely with the Founder to drive innovation and excellence.

Key Responsibilities:

• Architect and lead the migration from a .NET/Excel-based platform to a cloud-first solution using Azure and Python microservices.
• Act as both a technical leader and hands-on engineer, developing production code while mentoring a team of three junior developers.
• Design and implement scalable AI automation workflows that streamline document scanning, data extraction, and reporting processes.
• Manage the integration with Microsoft 365 tools, optimizing system performance and speed.
• Collaborate with executive leadership to architect the technical strategy and define product roadmaps and release milestones.
• Establish best practices for code quality, DevOps, and data governance to support scaling and growth.
• Oversee the transition from local execution environments to web-based compute systems, ensuring optimization for performance and scalability.

Ideal Candidate:

• 8 years in software engineering, with expertise in C#/.NET and Python.
• Proven experience in building and scaling SaaS or B2B automation platforms.
• Strong proficiency in Azure Cloud, APIs, and distributed architectures.
• Leadership skills with a knack for mentoring developers and balancing strategic vision with operational execution.
• Familiarity with AI/ML document processing frameworks (OpenAI, LangChain) and vector databases.
• Experience developing Microsoft Office Add-ins or similar integrations.
• Entrepreneurial spirit, comfortable in agile and resourceful early-stage environments.

Preferred Experience:

• Background in Commercial Real Estate (CRE), PropTech, or FinTech automation industries.
• Experience in launching or scaling a startup from MVP to a full-scale production product.
• Knowledge of FastAPI, Flask, or Django and data pipeline orchestration tools.

Compensation & Structure:

• Base salary: $120K $200K based on experience.
• Competitive equity package for long-term alignment.
• Flexible engagement model: Contract-to-hire or direct full-time W2 options.

About Mako Professionals: Mako Professionals is an elite IT staffing firm specializing in SAP, Oracle, Microsoft, and AI/Cloud technologies. We connect enterprise clients and groundbreaking innovators with top-tier consultants and technical leaders, delivering fast and precise talent solutions to propel companies towards success.

Embrace this rare opportunity to be at the forefront of AI-driven innovation in commercial real estate. Apply now and help shape the future of automation and technology!