Executive Search Success Story: Recruiting an AI-Native CTO to Rebuild the Technology Organization for a Miami Real Estate Technology Platform

How JRG Partners executed a confidential CTO search that replaced legacy technology leadership at a fast-growing Miami real estate technology platform with an AI-native Chief Technology Officer capable of re-architecting the product around machine learning, rebuilding the engineering organization, and restoring investor confidence ahead of a growth round.

Engagement Snapshot

Client Confidential — venture-backed real estate technology platform (name withheld at client’s request)
Industry Real Estate Technology & Marketplaces — encompassing property search, valuation, transaction workflow, and agent productivity tools
Geography Miami, Florida-headquartered — candidate mapping across South Florida, the Southeast, and national AI-native product and platform companies
Engagement Confidential retained search — AI-native CTO replacement with engineering organization rebuild and pre-funding mandate
Roles Searched Chief Technology Officer, VP of Engineering, Head of Machine Learning
Talent Assessed 310+ CTO, VP Engineering, and AI platform executives evaluated across marketplaces, proptech, and AI-native software companies
Timeline AI-native CTO placed in 55 days; engineering and machine learning leadership deployed within five months

The Challenge

A Miami real estate technology platform had grown rapidly on the strength of its marketplace, but its technology organization was built for a pre-AI product. The incumbent CTO had scaled infrastructure effectively but lacked the background to lead a machine learning transformation, and investors were signaling that the next funding round depended on a credible AI product roadmap. Executive leadership identified several critical vulnerabilities threatening their market position:

  • A monolithic architecture that made AI features slow and expensive to ship
  • No machine learning capability in the engineering organization beyond isolated contractors
  • AI-native competitors launching automated valuation and transaction tools faster
  • Investor concern that the technology leadership could not deliver the AI roadmap
  • Rising engineering attrition as senior developers sought AI-focused roles elsewhere
  • A CTO transition that had to be handled discreetly to protect the funding process

Recognizing that the company needed technology leadership built for the AI era, the CEO and board engaged JRG Partners to conduct a confidential search for an AI-native CTO, supported by a VP of Engineering and Head of Machine Learning. The company required an executive search partner who could distinguish AI-native technology leaders from traditional CTOs and manage a sensitive leadership transition ahead of a growth round.

Why They Chose JRG Partners

AI-Native Technology Leadership Focus

JRG Partners maintains a dedicated practice for AI-native CTO and CIO searches, with a clear methodology for evaluating whether a technology executive has built products and organizations around machine learning rather than adding AI as an afterthought.

Confidential Leadership Transitions

Our firm has extensive experience managing discreet executive replacements, protecting the organization, the incumbent, and external stakeholders throughout the process.

South Florida Technology Market Knowledge

Headquartered in Boca Raton, JRG Partners understands Miami’s expanding technology and venture ecosystem and how to position South Florida opportunities against established coastal technology hubs.

Our Executive Search Strategy

Phase 1 — Technology Leadership Assessment

Our consultants partnered directly with the CEO, board, and lead investor to define the AI-native CTO profile: platform re-architecture experience, hands-on machine learning product delivery, engineering organization rebuilds, and investor-facing credibility. This established clear criteria for distinguishing AI-native candidates from traditional technology leaders.

Phase 2 — Talent Identification & Mapping

Our research team performed an extensive talent mapping initiative targeting CTOs and senior engineering leaders at AI-native marketplaces, proptech companies, consumer platforms, and machine learning-driven software firms. Over 310 executive profiles were systematically assessed for AI product delivery at scale.

Phase 3 — Confidential Candidate Engagement

Priority during outreach was given to executives who had re-architected products around machine learning, built ML engineering teams from the ground up, and supported successful funding rounds. Outreach was conducted under strict confidentiality to protect the incumbent transition. Only candidates meeting these performance baselines advanced.

Phase 4 — Selection Process

Finalists completed a technical architecture review with an independent AI advisor engaged for the search and presented an AI product and platform roadmap to the CEO, board, and lead investor before reference verification focused on quantified product and organizational outcomes.

Results Delivered

JRG Partners successfully completed the multi-role mandate, placing an AI-native CTO and rebuilding the technology leadership team ahead of the growth round.

  • AI-Native CTO Appointed: A former CTO of an AI-native consumer marketplace joined the company and relocated to Miami, with the incumbent transition managed discreetly.
  • Platform Re-Architected: A modular, ML-ready architecture replaced the legacy monolith, cutting AI feature delivery time from months to weeks.
  • Machine Learning Capability Built: A dedicated ML engineering team was established under the new Head of Machine Learning.
  • Automated Valuation Launched: An AI-driven valuation and pricing tool shipped within eight months, matching AI-native competitors.
  • Attrition Reversed: Senior engineering attrition fell sharply as the organization gained a credible AI mandate.
  • Growth Round Closed: The company completed its funding round with technology leadership cited as a key confidence factor.

Key Outcomes

  • 310+ CTO, engineering, and AI platform executive profiles mapped across marketplaces and AI-native software companies.
  • Placed an AI-native CTO in 55 days through a confidential leadership transition.
  • Reduced AI feature delivery time from months to weeks through platform re-architecture.
  • Built a machine learning engineering function from zero to a fully staffed team.
  • Reversed senior engineering attrition within the first two quarters.
  • Directly supported a successful growth round through visible technology leadership upgrades.

Planning a Confidential AI-Native CTO Search in Florida or the Southeast?

JRG Partners recruits AI-native Chief Technology Officers and senior engineering leadership for venture-backed, private-equity-backed, and high-growth technology companies across Florida and the Southeast — discreetly, and with deep sector expertise.

Connect with our AI-native CTO and CIO search experts today to discuss your mandate.

Connect With Our AI-Native CTO & CIO Search Experts