Director, Member Experience

About the company

The company is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures, QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

About the role

Most companies solve growth by making service feel more distant, longer queues, more scripted responses, less sense that anyone remembers you. A few protect trust instead, but only by staying small enough for one person to hold every relationship in their head. Almost no one manages both scale and trust at once.

The company is building the system that does: a member experience function that gets more capable, not less personal, as it triples in size. That's the mold-breaking machine you'd be responsible for designing and running, one where most members are served through pooled, AI-assisted coverage and still feel like they have a person looking out for them, while a smaller population that genuinely needs deep, ongoing attention gets a real relationship, not a place in a queue.

This is a builder's role, not a caretaker's. You'll inherit a clear picture of where members actually need help across their lifecycle. The actual machinery, the industrial-grade mechanism that decides who gets what kind of attention and when, is yours to invent, tune, and run. Get it right and you will have built something genuinely rare: high-quality human connection at scale.

What you'll do

• Own the combined Support and Success function as one integrated Member Experience organization, including the interface between the two

• Design, launch, and continuously tune a tiered coverage model that gives a small number of genuinely high-need members real, dedicated attention while the large majority are served through a pooled, automation-assisted model, without the majority feeling like they've lost the relationship they were promised.

• Own the mechanism that decides who gets which level of coverage, and evolve it as you learn what actually predicts need versus what looked predictive in early data.

• Build and operate an intervention library: a small set of specific, driver-bound triggers (a payment failure, a stalled onboarding, a satisfaction score falling) that produce a defined action, on a defined channel, at a defined level of automation, each one measured against a target, and retired if it doesn't earn its place.

• Partner with the teams building AI-driven support (chat deflection) and in-product self-service tooling to convert as much routine volume as possible away from live human time, while making the judgment calls about where automation should stop and a human should start.

• Own quality as a non-negotiable floor while volume triples, first contact resolution and satisfaction do not regress, even if that means resolution time flexes or costs run ahead of pure efficiency gains in the short term.

• Stand up and lead a new pooled coverage function for members who are not receiving adequate attention under the current model, including building the team, the operating cadence, and the specific mechanics of how it delivers value at a materially different cost structure than the existing model.

• Build the measurement framework for both functions from first principles, favoring a small number of specific, durable metrics tied to real driver behavior over broad composite scores or vanity metrics, and use it to manage performance, not just report it.

What you'll bring

• 8+ years leading customer support, customer success, or member experience functions in a high-growth, high-trust business, fintech, financial services, or professional services strongly preferred.

• Direct experience designing or operating a tiered coverage model, pooled, automation-assisted coverage for the majority alongside real named coverage for a smaller segment, not just managing a uniform, one-size-fits-all book of business.

• A track record of building a mechanism, a trigger-based intervention, an automated workflow, a specific operating cadence, rather than only ever managing people against a target someone else designed.

• Experience transitioning an existing customer base from one coverage model to another, including what it costs in retention risk if done poorly, and the mechanisms you used to protect against that.

• A genuine point of view on where AI and automation belong in a service operation, and where they don't. You should be able to speak concretely about deflection, containment, and escalation design, not just enthusiasm for the category.

• Fluency with the basic economics of a service organization, loaded cost per role, what a pricing or packaging change does to unit economics, how to build a case for headcount or investment using real numbers.

• A bias toward mechanism over effort. When something is broken, your first instinct is to ask why the system produced that outcome, not to ask the team to work harder.

• Comfort inheriting a partially-defined strategic direction and being the one who resolves the remaining judgment calls, adapts it as new data arrives, and is fully accountable for the execution, not someone who needs the plan fully specified before they can move.

What we offer

• Remote-Friendly Environment: Flexibility to work from home while staying connected to the team. Please note that we're open to remote candidates within the U.S. for this role, but Bay Area-based employees follow a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Fresh Lunch: Provided on in-office days for those in a hybrid schedule.

• Commuter Support: $150 monthly reimbursement for transit expenses for those in a hybrid schedule.

• Health & Wellness: $200 quarterly reimbursement to support your well-being.

• Time Off: Flexible PTO plus 14 company holidays.

• Comprehensive Coverage: 100% medical, dental, and vision for employees; 75% coverage for dependents.

• Parental Leave: 16 weeks fully paid.

• Retirement & Ownership: 401k plan plus an equity package.

• Team Connection: Quarterly virtual events and an annual in-person summit.

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