Wing Assistant is a venture-backed, Silicon Valley-based startup with global operations. We match US businesses with dedicated, fully managed remote professionals (executive assistants, customer service reps, healthcare admins, bookkeepers, and more) and run the delivery behind them: recruiting, onboarding, management, and support. We're also building exciting AI technologies to help clients get even more done across our Wing suite and sister companies we operate in the AI space.
Our talent and delivery teams are based in the Philippines; our clients are mostly in the US; our leadership works across Hong Kong and the US. We've scaled fast. Now we're obsessed with getting every customer we win live quickly, and keeping them for the long haul.
The Role
The biggest lever on Wing's growth is what happens after a customer signs: how quickly they get value, and how long they stay. We're hiring one person to own the entire post-sale journey (onboarding, activation, and retention) from the moment a deal closes to month 12 and beyond.
This is not an advisory role. You won't hand off a deck and walk away. You'll diagnose where and why customers stall or leave, build the systems and tools to fix it, and hold multiple teams accountable to the numbers. If you've spent years recommending changes and want to be the person who actually makes them happen, this is that job.
What you'll own
The onboarding pipeline. Every new account from signed deal to fully live. You know where every account sits, where it's stuck and why, and you make sure it moves faster.
Activation and early-life health. The first months decide whether a client stays. Define what a healthy start looks like, spot accounts going off track and intervene early.
Retention and churn as numbers. Define them, measure them and break them down (logo vs. revenue, early-life vs. mature, by role, segment, acquisition channel and team). Set the targets and own the trend lines.
Root-cause analysis. Funnels, cohorts, survival curves, leading indicators. Go beyond the dashboard into the qualitative and raw data to find what really drives outcomes.
Process improvement. Map the handoffs across teams, find the friction, redesign the process, run experiments and measure the impact.
Building tools. Vibe-code dashboards, alerts and workflow tools using Claude and other AI coding tools. Ship useful things in days, not quarters.
Deep data work. Write the SQL, reconcile the sources and build the models. When two systems disagree, you find out which one is right and why.
Stakeholder leadership. Work with sales, recruiting, customer success, finance, product and our Philippines operations team: people from very different backgrounds, functions and time zones. Drive change through clarity and evidence often without direct authority.
Reporting to leadership. A crisp weekly view of pipeline, activation and retention health: what changed, and what you're doing about it.
What success looks like
First 30 days: You've mapped the customer journey end to end, have access to every relevant data source, and have built trusted baselines for the metrics you own.
First 60 days: You've identified the highest-impact opportunities with hard evidence, launched the first interventions, and shipped your first tools.
First 90 days: You can show measurable improvement on at least one core metric, yourun a weekly operating cadence, and the tools you built are used daily by the teams.
Consulting pedigree. 3–7 years of experience, including at least 2 years in management or strategy consulting (MBB, Tier 2, Big 4 strategy or a strong boutique), or an equivalent analytical role such as strategy, BizOps or PE portfolio operations.
Relentless attention to detail. You reconcile numbers to the dollar. You notice the one row that's wrong. Sloppy data bothers you.
Strong data skills. Comfortable working directly with databases, with spreadsheets and BI tools. Programming experience is a plus, but not necessary.
AI-native. You use Claude (or similar) every day, are comfortable connecting AI tools to data through MCPs, building workflows and dashboards and have built working tools with AI coding assistants (e.g. Claude Code, Cursor, Replit, Lovable). Show us
something you've built.
Fluent English, written and spoken.
Ownership mentality. You thrive in ambiguity, bias toward action, and care about outcomes more than activity.
Comfortable with many stakeholders across cultures, seniority levels and functions.
Working Arrangements
Remote, full-time role. Occasional in-person meetings in Hong Kong.
Location: Hong Kong.
Hours: Our clients and many team members operate on US time. Your working day will generally run from the evening into the night, Hong Kong time. This is a core requirement of the role, not an occasional ask.
Travel: Occasional trips to our operation center in the Philippines.
Pace: This is an intense, high-ownership role in a fast-moving company. Expect high standards, tight feedback loops and real accountability for results. It's a great fit if you want to grow fast and see your work move the numbers, and probably not the
right fit if you're looking for a steady 9-to-5.
Commitment: This is a high-ownership, full-time role, and we expect it to be your only professional commitment. If you have other employment, consulting work or business interests, please mention them when you apply so we can discuss them openly.
How to apply
Send your CV and a short note (no more than 200 words) about a time you found the number nobody else had noticed, and what happened next. Links to anything you've built with AI tools are a strong plus.
Shortlisted candidates will complete a practical case exercise using real-world style data.
Fine Print
Background and reference checks. Final-stage candidates may be asked to complete background and reference checks, with their consent and in line with applicable law.
Equal opportunity. Wing is an equal opportunity employer. We hire on merit and welcome applicants of every background, regardless of race, colour, religion, sex, sexual orientation, gender identity, age, disability, marital or family status, nationality or any other characteristic protected by law.
