Retention Operations Assistant - Remote

Full-Time | 1099 Contractor | Monday–Friday, 8:00 AM–5:00 PM Pacific Time

We’re looking for a sharp, highly organized Retention Operations Assistant to support our Head of Client Retention at a fast-growing U.S.-based technology company.

This is a great role for someone who likes keeping a lot of moving pieces organized, naturally follows through, communicates exceptionally well, and gets satisfaction from making sure nothing falls through the cracks.

This is not a highly technical position, and you do not need previous AI experience. Prior experience as an Executive Assistant, Operations Assistant, Customer Service Representative, Account Coordinator, or similar role is preferred - but we care just as much about how you think, communicate, prioritize, and take ownership.

What You'll Be Doing:

You'll work closely with our Head of Retention to keep client accounts, follow-ups, and internal action items organized and moving forward.

Your day-to-day responsibilities will include:

Reviewing client and internal communications each morning and identifying what needs attention
Creating a clear, prioritized daily rundown for the Head of Retention
Monitoring open client issues and making sure next steps, statuses, and follow-ups stay current
Following up with internal team members on outstanding action items and deadlines
Following up with clients by phone, text, email , and Slack when information, scheduling, or a response is needed
Coordinating calendars and helping schedule client meetings with the appropriate team members
Preparing account information and context before important client conversations
Researching account history when a client issue is escalated, including reviewing messages, notes, timelines, recordings, and other available information
Summarizing complicated situations into clear, useful updates so leadership can quickly understand what happened and make a decision
Running basic test calls and documenting anything that needs further review
Drafting clear, professional client email s
Keeping our internal retention systems accurate and up to date
Catching overdue or missing items before they become bigger problems
Making sure open loops actually get closed

You will not be responsible for making major client retention decisions, negotiating refunds, or independently resolving complex escalations. Your job is to gather the right information, keep things moving, and make sure the Head of Retention has what she needs to make those decisions.

The Person We're Looking For

You may be a great fit if you're the type of person who sees five open items and immediately starts figuring out what matters most, who owns each one, and what needs to happen next.

We'd love someone who is:

Extremely organized - you can manage multiple clients, deadlines, and follow-ups without losing track of details
Proactive - you look for the answer before immediately asking someone else
Resourceful - if you don't know where something is, your instinct is to figure out where to look
Strong at prioritization - you understand that not every task is equally urgent
Excellent at follow-through - when someone says they'll have something done tomorrow, you remember to check tomorrow
A critical thinker - you don't simply copy information; you try to understand what actually happened
Concise - you can turn 20 messages into the five sentences your manager actually needs
Calm and professional - especially when communicating with a frustrated client
Comfortable holding people accountable - you're willing to politely follow up until something is completed
A strong written and verbal English communicator
Quick to learn new systems and processes
Reliable and consistent

We don't expect you to know everything on day one. We do expect you to learn quickly, take good notes, use the resources you're given, and become increasingly self-sufficient as you're trained.

Requirements

You must:

Be available Monday–Friday, 8:00 AM–5:00 PM Pacific Time
Be comfortable working as a 1099 independent contractor
Have a reliable, high-speed internet connection
Have a reliable computer and professional remote-work setup
Have strong spoken and written English
Be comfortable communicating with U.S.-based clients and team members
Be comfortable using tools such as Slack, CRM systems, calendars, email , and Zoom
Be comfortable making outbound client follow-up calls when necessary
Be comfortable being on camera for internal Zoom meetings
Maintain a professional appearance and environment while on camera

Prior experience in executive assistance, operations, customer service, account management, or client success is preferred but not required for an exceptional candidate.

This Role Probably Isn't for You If...

We want to be transparent about the environment you'll be joining.

If you need your manager to tell you what to do next throughout the day, this probably won't be the right fit.

If something is missing, we want your first instinct to be:

“Let me see if I can figure this out.”

If someone owes you an answer, we want you comfortable following up.

If ten things happen at once, we want you thinking about priority, rather than simply doing whichever task you saw first.

And if you discover something that requires a leadership decision, we want you to gather the facts, organize them clearly, and escalate it—not guess.

You'll receive training, processes, and support. The goal is for you to become someone your manager can depend on, not someone she has to constantly manage.

Compensation & Opportunity

$400–$600 USD per month, depending on experience and demonstrated ability.

This is a full-time remote contractor position with consistent Monday–Friday hours. We're looking for someone who wants stability, enjoys becoming excellent at their role, and would like the opportunity to grow alongside a growing company.

How to Apply

Please submit your resume for consideration.

We're intentionally selective about this role because the person we hire will become an important part of our day-to-day operations.

Qualified applicants will be invited to complete a short video questionnaire so we can learn more about how you communicate, think, and approach your work.

Candidates who perform well on the questionnaire will then receive a link to schedule an interview with our team.

If you're organized, resourceful, thoughtful, and the person people naturally rely on to keep things moving—we'd love to hear from you.