workable
Senior Client Retention Specialist
AI Acquisition
Remote, USA
Full-time
Senior · 5–8 years experience
Remote
Discovered 1 weeks ago
Full Job Posting
Requirements
- What You Actually Do
- Own the hard cases:
- Take full ownership of escalated client situations — from first signal through to resolution — applying structured thinking at every stage, not reactive problem-solving
- Diagnose the root cause behind every at-risk engagement and build a targeted intervention before the situation deteriorates further
- Negotiate outcomes that protect the client relationship and the company's commercial interests — without compromising either
- Maintain meticulous case records that support continuity, accountability, and pattern recognition across the book
- Protect and grow revenue:
- Monitor client engagement signals and identify early indicators of dissatisfaction or churn risk before they surface as formal escalations
- Develop and execute retention strategies that address underlying issues — not just surface-level complaints
- Work cross-functionally with Customer Success, Sales, and Operations to close the gap between what was promised and what is being delivered
- Track and report weekly on retention metrics, case outcomes, revenue protected, and churn trends — with clear recommendations, not just data
- Build the function:
- Contribute to the development of retention playbooks, escalation frameworks, and client support systems that scale beyond you
- Identify patterns across accounts that signal broader delivery or operational issues requiring intervention
- Act as the internal voice of the client — ensuring leadership and delivery teams understand the downstream cost of service gaps
- Propose and implement process improvements that reduce escalation volume and resolution time over time
- 5–8 years in a senior client-facing role — spanning client retention, revenue protection, customer success, or escalation handling within a high-growth service, agency, or tech-enabled business
- Proven track record managing complex, high-value client situations with measurable retention outcomes
- Prior exposure to cross-functional environments — working alongside Sales, Operations, and Leadership to resolve client issues at pace
- Experience contributing to retention policy, escalation frameworks, or client risk management systems
- Skills & Competencies
- Expert-level negotiation and de-escalation — able to navigate emotionally charged, commercially sensitive conversations with composure and precision
- Commercially sharp — understands the revenue impact of every decision and applies judgment accordingly, not just policy
- Strong analytical ability — reads retention data, identifies risk patterns, and turns insights into action fast
- Excellent written and verbal communication — clear, professional, and persuasive in every client-facing and internal context
- Meticulous documentation habits — maintains thorough records that support continuity, accountability, and process improvement
- Mindset & Behavioural Fit
- Senior ownership mentality — operates independently, takes full accountability for outcomes, and doesn't wait to be managed
- Solutions-oriented and calm under pressure — approaches escalations with structure and clarity, not reactivity
- High commercial integrity — balances genuine client empathy with the company's financial interests without compromising either
- AI-native or highly AI-fluent — actively uses AI tools to enhance output quality, response speed, and documentation efficiency
- Proactive risk detector — spots churn signals early and acts before situations deteriorate
- Discreet and professional — exercises sound judgment in handling confidential, sensitive, and commercially significant matters
- You need a calm, structured environment with predictable, low-stakes caseloads
- You measure success by how many cases you close, not by how much revenue and trust you protect
- You are more comfortable following a retention script than diagnosing what's actually wrong
- You need to be managed through difficult conversations instead of leading them
- You are looking for a transactional support role with clear escalation paths above you
Requirements
- Experience
- You Will Probably Not Fit If:
Benefits
- What You Get
- Competitive compensation tied to retention and revenue protection outcomes you own
- Fully remote — US, UK, UAE, Canada, or Australia
- Full-time, stable role at a profitable bootstrapped company — no runway anxiety, no pivots every quarter
- Direct line to senior leadership that has built and scaled products past $100M in revenue
- Real growth track — perform in this seat and the scope expands: retention team lead, broader ops ownership, or a cross-functional leadership role
About AI Acquisition
Software & SaaS153 employeesFounded 2021
AI Acquisition is a private AI software and consulting company helping entrepreneurs build and scale AI-powered businesses.
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