AI-Driven Customer Success Manager – PropTech Scale

trg.; Greater London; On-site; GBP 70,000 - 95,000; Full time

Job summary

trg. is seeking a Customer Success Manager to own relationships with property management clients and drive conversion from pilot to paid while expanding accounts. You will design AI-powered workflows, monitor health metrics, and help shape the product roadmap through client feedback.

This is a fast-moving, AI-first CS role in a growing startup. You’ll collaborate with Sales, Engineering, Product and AI teams to ensure a seamless client experience, diagnose issues, and scale the CS function

Qualifications

• 3+ years in a client-facing B2B SaaS role.
• Experience designing and deploying AI-powered workflows that solve real operational problems.
• Experience managing enterprise or high-value client relationships and driving product adoption.
• Track record of converting customers from pilot to paid and maintaining strong retention.
• Comfort with technical concepts — APIs, integrations, data imports/exports, webhooks.
• Strong diagnostic skills and a methodical approach to root-causing issues.
• Excellent written and verbal communication, able to translate technical topics for non-technical clients.
• Comfort working in a fast-moving early-stage startup environment.

Responsibilities

• Owning end-to-end client onboarding, from sales handoff to go-live - kickoff calls, timelines, technical setup coordination (data imports, communication channel provisioning, user accounts), data quality validation, and client training
• Designing and deploying AI-powered workflows for health monitoring, escalation triage, onboarding tracking, performance reporting and feedback routing
• Building the tooling and processes that let a small CS team scale with the client base rather than headcount
• Deciding what stays human (relationship calls, strategic advice, complex escalations) versus what gets automated
• Managing ongoing client relationships through regular check-ins and performance reviews, and monitoring client health metrics (resolution rate, escalation volume, response times, satisfaction)
• Proactively spotting issues - data quality gaps, rising escalations, underused features - and maintaining each client's knowledge base
• Owning pilot-to-paid conversion, retention, and identifying account expansion opportunities
• Translating customer feedback into structured product tickets and working with Product/Engineering so client insight shapes the roadmap
• Diagnosing whether issues are configuration, data quality, user error or product bugs, resolving what you can, and escalating confirmed bugs with clear repro steps

Skills

Client-facing SaaS

AI workflow design

Enterprise customer management

Product adoption strategies

APIs & data concepts

Diagnostics & root cause analysis

Excellent communication

Startup environment adaptability

Tools

HubSpot

Notion

Slack

Job description

trg. is seeking a Customer Success Manager to own relationships with property management clients and drive conversion from pilot to paid while expanding accounts. You will design AI-powered workflows, monitor health metrics, and help shape the product roadmap through client feedback.

This is a fast-moving, AI-first CS role in a growing startup. You’ll collaborate with Sales, Engineering, Product and AI teams to ensure a seamless client experience, diagnose issues, and scale the CS function