Retention Manager

About the role

We are looking for a Retention Manager to lead our client retention function: building the strategy, running the team, and personally stepping in when the stakes are too high to leave it to anyone else.

In this role, you will own how RemoteLegalStaff retains its law firm clients. That means leading a team of Retention Specialists, developing the playbooks and processes they work from, tracking the health of the client portfolio at a macro level, and serving as the senior voice in the room when a major escalation cannot be resolved at the team level. You will work closely with Client Success and leadership to ensure that client dissatisfaction is caught early, addressed decisively, and, wherever possible, turned into a strengthened relationship.

This is a strategic and operational role in equal measure. You will be expected to build, not just execute. You will define what good retention looks like at RLS, raise the standard of how your team performs, and be personally accountable for the outcomes across the entire at-risk portfolio. If you are someone who thrives on diagnosing problems, building systems, and coaching others to perform at a high level, this role was designed for you.

What you'll do

Team Leadership

• Lead a team of Retention Specialists, owning their day-to-day performance, development, and the quality of their client interventions
• Run regular 1-on-1s, call reviews, and coaching sessions with your direct reports; give direct, specific feedback and hold a high standard
• Serve as the escalation point for situations your team cannot resolve independently; step in directly on major escalations that require a more senior presence and see them through to resolution
• Onboard and ramp new Retention Specialists as the team grows
• Identify gaps in your team's skills and close them through coaching, training, and process improvement

Retention Strategy

• Own the retention function at RLS: define how it works, what it measures, and how it improves over time
• Build and maintain the playbooks, frameworks, and scripts your team uses to approach at-risk accounts, and update them as you learn what works and what doesn't
• Monitor client health signals at a portfolio level, ensuring at-risk accounts are identified and assigned before they reach a crisis point
• Report on retention outcomes to leadership: churn trends, intervention success rates, patterns in why clients leave, and recommendations for systemic fixes
• Identify root causes of client dissatisfaction that go beyond individual accounts and surface them to the relevant teams
• Partner with Client Success and leadership to ensure the retention function is integrated with, not siloed from, the broader client experience

Client Escalations

• Step in personally on the highest-stakes escalations: situations where the client relationship is at serious risk, where a Senior Account Manager has reached their ceiling, or where the outcome has a material impact on the business
• Lead those conversations with composure, authority, and a clear plan; you are the most senior voice the client encounters in a crisis, and you need to be the reason they stay

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What we're looking for

• 5+ years of B2B client-facing experience in account management, customer success, client retention, or a related field, with a meaningful portion of that time spent handling at-risk or churning accounts
• Team management experience is required. You have led a team of client-facing professionals, coached them through difficult situations, and are accountable for their results. This is non-negotiable.
• Excellent spoken and written English. You will be representing RemoteLegalStaff in the most difficult client conversations we have. Clarity, authority, and composure under pressure are non-negotiable.
• Proven ability to build and improve processes, not just execute them; you have owned a function before and made it better
• Strong data orientation; you track what matters, report on it clearly, and use it to make decisions
• Deeply comfortable with hard conversations; you can take accountability without being defensive, rebuild trust that has been damaged, and stay steady when a client is not
• Available to work U.S. business hours with a start time between 6:00 AM and 8:00 AM PST
• Highly organized with the ability to manage both team-level priorities and individual escalations simultaneously without either slipping
• Good judgment on when to escalate internally, when to hold the line with a client, and when an account is not recoverable, and the courage to act on that judgment
• Confident and poised when speaking with attorneys and legal professionals at the most senior levels, our clients are lawyers, and the escalations that reach you are not the easy ones
• Collaborative and effective with cross-functional partners; your relationships with Client Success and leadership directly determine how effective the retention function is
• Self-starter who can operate with significant autonomy and doesn't need the strategy to be handed to them
• Preferred backgrounds: staffing, professional services, financial services, or other service-based B2B environments
• Experience in the legal industry is a plus, but not required
• Previous remote or hybrid work experience required; fully remote experience strongly preferred

What success looks like

• In your first 90 days, you will have a clear read on the current state of the retention function: what is working, what is not, and what needs to be built. You will have taken ownership of your team, established your standards, and begun executing retention interventions directly on the most critical accounts. Leadership will trust your read on the portfolio and your plan for improving it.
• Over time, success means measurable improvement in client retention rates, a team that performs consistently and develops under your leadership, a playbook that actually reflects how great retention is done at RLS, a Client Success team that is meaningfully better at handling escalations because of the coaching and training you've invested in them, and a seat at the table when leadership is making decisions that affect the client experience.

What we offer

• Fully remote position with a flexible work schedule
• Competitive base salary
• Annual performance bonus
• Anniversary loyalty bonuses
• Company-sponsored health insurance
• Generous PTO that increases with tenure (up to 30 days per year)
• Birthday PTO day
• 7 U.S. paid holidays
• 5 paid sick days per year
• Bereavement leave
• Additional unpaid personal leave available
• Home office stipend for equipment and workspace upgrades
• Computer replacement stipend
• Monthly internet allowance (increases with tenure)
• Professional development and training programs
• Education support for high performers
• A collaborative, supportive team culture where people are genuinely invested in each other's success
• A fast-moving environment where your work has real visibility and direct impact
• Clear path to growth: we promote from within and reward people who perform

How to apply?

• Start your application message with B2B or B2C, depending on where your primary client management experience lies. Then, in 2–3 sentences, describe your background — the industry you worked in, the type of clients you managed, and the scope of your accounts. Applications that do not follow this format will not be reviewed.

How our hiring process works:

We are a fully remote company, and our hiring process reflects that. The first stages are completely asynchronous: no surprise calls, no scheduling pressure. You will complete a short written application and, if selected, move through an async assessment at your own pace. Candidates who advance through the initial stages will then be invited to schedule a live interview.

We communicate clearly at every step and respect your time throughout!