Fifth Wall Analytics, Inc. Engagement Manager Chicago, IL · Remote · Full time

You will own 2-3 client relationships and lead engagements from initial discovery through implementation and ongoing expansion. You will sit at the intersection of consulting, AI solution design, and client success – translating ambiguous real estate problems into clear, executable plans and measurable outcomes.

About Fifth Wall Analytics, Inc.

Fifthwall Analytics is building the operating layer for AI-powered real estate businesses. We partner with real estate companies to identify high-value operational pain points, then design and deploy tailored AI solutions that drive measurable outcomes.

Description

As Engagement Manager, you will own 2-3 client relationships and lead engagements from initial discovery through implementation and ongoing expansion. You will sit at the intersection of consulting, AI solution design, and client success – translating ambiguous real estate problems into clear, executable plans and measurable outcomes.

What you’ll do

  • Own client relationships end-to-end, serving as the primary relationship manager and day-to-day point of contact.
  • Lead discovery engagements (typically 2–3 weeks):
  • Conduct stakeholder interviews across business, operations, and technology teams
  • Map current-state processes and decision flows
  • Identify, size, and prioritize pain points that are well-suited for AI intervention
  • Translate business needs into structured problem statements, technical briefs, and solution hypotheses in partnership with Product and Engineering.
  • Manage engagement scope, timelines, deliverables, and client communications with high precision and polish.
  • Present findings, recommendations, and progress updates to senior audiences (VP , C-suite) with confidence.
  • Drive implementation success by coordinating across internal technical teams and client stakeholders to support deployment and adoption.
  • Identify expansion opportunities over time by linking delivered outcomes to additional high-value use cases.
  • Serve as an internal feedback loop—bringing field insights back to improve the platform, packaging, and go-to-market motion.
  • Travel to client sites as needed for relationship-building and on-site discovery sessions.What we’re looking for


Required

  • 7-10+ years of experience in tech enabled services consulting, strategy, or a high-velocity, client-facing role specifically in the commercial real estate domain
  • Demonstrated ability to elicit business requirements from non-technical stakeholders and translate them into clear, testable problem statements.
  • AI-native mindset: you actively use AI tools in your work and understand practical
  • capabilities, limitations, and adoption considerations.
  • Outstanding written and verbal communication: comfortable running executive meetings and producing crisp one-pagers and client-ready deliverables.
  • Strong organizational skills and comfort managing multiple engagements simultaneously.
  • Entrepreneurial orientation: energized by building new processes, templates, and playbooks in a lean environment.


Preferred

  • Experience at a Series A–C startup or in roles requiring significant cross-functional ownership.
  • Familiarity with AI/ML solution configuration and/or data pipeline concepts (you don’t need to build them, but should be able to speak to them).
  • Track record of growing client relationships beyond the initial scope through demonstrated outcomes.


How engagements work (3-phase model)

1. Discovery (Weeks 1–3)

  • Stakeholder interviews
  • Process mapping and current-state assessment
  • Pain point prioritization and use-case selection
  • Output: prioritized roadmap + technical briefs + success metrics


2. Build (Weeks 4–8)

  • Partner with technical team on backend data work and AI solution configuration
  • Validate hypotheses with client stakeholders through iterative check-ins
  • Output: configured solution(s), implementation plan, and readiness checklist

3. Implementation & Expansion (Ongoing)

  • Live deployment and adoption support
  • Measurement and iteration against success metrics
  • Relationship deepening and identification of next use cases
  • Output: sustained outcomes and account growth plan