Head of Customer Success

Head of Customer Success — Crown Macro
About Crown Macro

Crown Macro is a modern financial media business for self-directed traders and active investors. We publish institutional-quality macro analysis every day across a video series, a weekly research letter, and live desk access, and we run a fast-growing subscription business with a large and engaged audience.

The Role

We're hiring a Head of Customer Success to own the entire customer experience after someone becomes part of Crown Macro: onboarding, product education, support, subscription and billing, feedback, retention, and recovery when something goes wrong.

This is a senior operating role, not a customer-service management position. You'll start hands-on, personally supporting customers, resolving issues, and learning where they succeed, where they struggle, and why they leave. From there you'll build the systems, processes, tooling, and team that let us deliver fast, thoughtful, high-quality support at scale.

The best support isn't just closing tickets. It's one of the strongest sources of product intelligence a company has. We want someone who can solve a customer's problem personally, find the systemic cause, work with product and engineering to eliminate it, and build the process that prevents the next hundred customers from hitting the same wall. Often the best support interaction is the one the customer never needs to have, because the underlying problem is gone.

What You'll Own

Support, end to end. Own the support function and personally handle customer conversations in the early stage: account, billing, subscription, product, and access issues. Set clear standards for response time, resolution quality, tone, and escalation, and build escalation paths for technical problems, payment failures, account access, and complaints.

Systems that scale. Select and continuously improve the tools for communication, ticketing, knowledge management, reporting, and automation. Build self-service resources — help docs, FAQs, account-management tools, contextual product guidance — so support scales without becoming impersonal or headcount-bound. Use automation and AI where they improve speed, and keep human judgment where it matters.

Support as product intelligence. Work with product and engineering to reproduce bugs, prioritize recurring issues, and eliminate root causes. Serve as a consistent voice of the customer: capture, categorize, and route feedback to product, engineering, editorial, growth, and leadership, and separate one-off requests from patterns that warrant real change.

Onboarding and education. Improve onboarding so new subscribers quickly understand the product and reach value early, and build education programs that help them get more from Crown Macro's research and tools.

Retention and churn. Identify subscribers who are struggling or likely to cancel and intervene appropriately. Own cancellation and save flows with respect for the customer, without dark patterns or friction traps. Analyze cancellation reasons, usage, billing issues, and feedback to find preventable churn, and partner with growth and product to improve retention and lifetime value.

Metrics and reporting. Define and monitor the measures that reflect customer health: support volume, response and resolution time, contact rate, satisfaction, cancellation reasons, retention. Build reporting that shows leadership what customers are actually experiencing, and set service-level expectations and capacity models as the base grows.

Build the team. As volume requires, determine the right roles, staffing, and structure, then recruit, train, and manage the team. Create playbooks, documentation, and quality standards so new hires ramp quickly, and build a culture of customer ownership rather than queue-clearing.

Strategic partner. Work directly with the founders as a senior voice on product, retention, and customer-experience strategy.

Your First Year

• Take ownership of support and establish a consistently high standard of service.
• Develop a deep understanding of our customers, their most common problems, and why they contact us.
• Put clear processes, escalation paths, documentation, tooling, and reporting in place.
• Significantly reduce unnecessary contacts by fixing recurring product, billing, onboarding, and communication problems.
• Stand up a voice-of-the-customer program that turns conversations into insight for product, engineering, editorial, and leadership.
• Build a systematic understanding of cancellation reasons and cut preventable churn.
• Establish the metrics and operating cadence we'll use to evaluate customer experience.
• Begin building the team as volume and complexity require — a function that can support far more customers without support headcount growing linearly with the subscriber base.
  

Who You Are

You're an experienced customer success or customer experience leader from a subscription, fintech, financial media, SaaS, research, education, or membership business. You pair strong customer instincts with operational discipline, and you're equally comfortable talking to an unhappy customer, investigating a technical issue, reviewing billing data, writing a process, analyzing cancellations, and designing the org that will eventually do all of it at scale.

You're empathetic without being customer-controlled — you know the difference between listening carefully and implementing everything customers ask for. You write exceptionally well and can explain complex situations clearly and calmly. You have strong judgment about when to solve immediately, when to escalate, when to compensate, when to push back, and when a small complaint points to a much larger problem.

Particularly Valuable Experience

• Building or leading customer success or support for a subscription business, ideally paid newsletters, financial media, research platforms, fintech, or membership products.
• Working with sophisticated individual investors or traders.
• Building a customer success function from an early stage.
• Managing subscription billing, cancellations, refunds, failed payments, and account access.
• Working closely with engineering and product to eliminate recurring customer problems.
• Designing onboarding and customer education programs.
• Using customer feedback and behavioral data to improve retention.
• Developing support automation, AI-assisted workflows, and self-service systems.
• Scaling customer operations from thousands to tens of thousands of paying customers.
  

What This Role Is Not

• Not a ticket-answering role, and not traditional enterprise customer success built around quarterly business reviews, account plans, and scheduled check-ins.
• Not retention-at-all-costs built on making cancellation painful.
• Not a management layer between customers and the people who can actually fix their problems.
• Not "hire more agents as volume grows." This role owns the system that helps customers succeed, resolves problems fast, finds what's causing them, and keeps making the experience better.
  

What We Offer

• A large, growing subscriber base and direct access to customers, with real room to improve their experience.
• A differentiated product in a large, culturally relevant market.
• Direct access to the founders and meaningful influence over product, operations, retention, and strategy.
• The chance to build the customer success function, team, and operating model from the ground up.
• Close collaboration with product and engineering — the ability to actually fix systemic problems, not just apologize for them.
• A company willing to invest in automation, tooling, product, and people when they materially improve the customer experience.
• Competitive compensation with meaningful upside tied to company and individual performance.