Senior Client Retention Specialist
AI Acquisition · Remote
The Seat
You own the most commercially sensitive client relationships in the business. The ones where trust is fragile, stakes are high, and the wrong move costs more than a contract — it costs the relationship.
This is not a support role. It is not a processing role. It is a senior commercial seat for someone who can walk into a difficult conversation, diagnose what's actually broken, and turn a client who is ready to walk into one who stays, re-engages, and expands.
In the early weeks you will be close to the ground — learning the client base, understanding the patterns, and making sure nothing falls through. That proximity is the input. The retention outcomes you drive from it are the job.
You report into senior leadership. You own the cases. You own the outcomes.
The Company
AI Acquisition is a multi-8-figure business helping founders and operators scale with AI. 3,000+ clients. 200+ mastermind participants. A sales and delivery engine built for speed and scale.
Growth is happening faster than most companies ever see. This seat exists because the client base is scaling, the stakes per account are real, and we need someone senior enough to protect revenue and relationships at pace.
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
Requirements
Experience
- 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 Will Probably Not Fit If:
- 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
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