Product Manager

CloudSquad is looking for a hands-on Product Manager to help shape and deliver AI-powered products for a rapidly growing real estate accounting firm based in the U.S. You will be joining a high-impact delivery team focused on improving operational efficiency, reducing churn, and unlocking new product capabilities through automation and applied AI. Your work will directly influence business-critical products and initiatives such as:

• A multi-tenant web portal for operational workflows and analytics
• AI-powered financial analysis and anomaly detection
• Client communication intelligence (calls, emails, sentiment analysis)
• Workflow automation across accounting, operations, and client management systems

• Own product discovery, prioritization, and delivery of new platform capabilities across multiple product areas.
• Translate business needs into clear product requirements, user stories, tickets, and sprint goals for engineering teams.
• Collaborate closely with engineering and business stakeholders to define solutions that balance user value, feasibility, and speed of execution.
• Drive end-to-end product development for AI-powered features, including workflow automation, conversational analysis, and operational intelligence.
• Define and improve product workflows, UX, and information architecture to simplify complex operational processes.
• Leverage AI tools to accelerate product research, documentation, requirement generation, analysis, and decision-making.
• Coordinate delivery across multiple workstreams, ensuring clear communication and smooth execution in an async-friendly environment.
• Support sprint planning, product alignment, and stakeholder communication to maintain momentum across fast-moving initiatives.
• Collaborate with leadership to shape roadmap priorities and validate product direction through iterative experimentation.
• Analyze user feedback, operational pain points, and business metrics to identify opportunities for product improvement and churn reduction.
• Act as a bridge between users and engineering by supporting users through Slack, resolving blockers, and identifying product improvement opportunities.
• Schedule and lead user feedback sessions to uncover operational pain points, validate product decisions, and improve adoption.

Requirements

Must-Have:

• 3+ years of experience in Product Management delivering software products.
• 3+ years of Project Management experience coordinating cross-functional initiatives.
• Demonstrated hands-on use of AI tools for Product Management workflows (e.g., research, requirement writing, analysis, prioritization, prototyping).
• Experience translating ambiguous business needs into actionable product requirements and engineering deliverables.
• Strong product thinking with the ability to balance user needs, business priorities, and technical constraints.
• Excellent communication skills (English, async-friendly).
• Strong ownership mindset and ability to work independently in a fast-moving environment.

• Experience working closely with engineering teams in technical product environments.
• 5+ years of software development experience or a strong technical background working closely with engineering teams.
• Design experience (UX/UI, prototyping, information architecture, or product design thinking).
• Familiarity with AI-powered products, automation systems, or operational tooling.
• Experience in B2B SaaS, accounting, fintech, proptech, or operational platforms.

• A front-row seat in building applied AI features that directly replace manual work.
• Opportunity to own product direction from idea → delivery → adoption.
• Work alongside a lean, senior team driving a platform with potential to scale to 10,000+ users.
• Help define CloudSquad’s product delivery playbook for AI-powered operational systems.
• Join a project with founder-level buy-in, budget, and momentum.