Founding Customer Success & Operations Lead

About Autumn

Autumn is building the AI operating system for independent hotels.

Hotels are still run on an extraordinary patchwork of legacy software, agencies, spreadsheets, and manual workflows. Pricing lives in one system. Marketing in another. Guest data somewhere else. Critical decisions are still made manually across teams and vendors that rarely speak to one another.

We are building one AI native platform that brings this work together and increasingly does it for the hotel.

We are starting with the workflows closest to revenue, including digital marketing, and expanding from there into the broader hotel operating stack.

The opportunity is enormous. Independent hotels represent a massive, underserved market, and the software they rely on is decades behind what modern businesses expect.

Autumn recently raised the largest seed round in hotel tech history, led by Bessemer. We are building a small, exceptional team in person from our waterfront office in Williamsburg. We are solving a real hair on fire problem, closing 85% of the calls we schedule with cold outbound emails!

We are now hiring our Founding Customer Success & Operations Lead to build the function that owns every customer from the moment they sign.

For the right person, this can grow into leadership of Customer Success and Customer Operations at Autumn.

The Role

You will own everything that happens after a hotel says yes.

That starts with getting the property live quickly and correctly. It continues with making sure the customer sees value, understands performance, stays with Autumn, and expands over time.

Today, that means being both an operator and a builder.

You will personally onboard hotels. You will get into the tracking stack when something does not look right. You will speak directly with hotel owners and general managers. You will spot an account at risk before they tell us. And you will turn everything you learn into systems that allow Autumn to serve hundreds and eventually thousands of hotels exceptionally well.

There are three major parts to the role.

1. Implementation: Own the journey from signed contract to live customer.

2. Customer Success: Own the relationship once the hotel is live. Help owners and GMs understand what Autumn is doing, what is working, where opportunities exist, and what needs to change. Own retention, expansion, and customer trust.

3. Build the machine: Today, many of these workflows still depend on judgment, founder context, and manual intervention. Your job is to turn them into a scalable operating system.

This is a true player builder role. For a while, you will do the work yourself. Depending on your trajectory you will hire the team, train them on the systems you built, and increasingly lead the function.

What You'll Own

• Own every customer from AE handoff through onboarding, launch, retention, and expansion
• Get new hotels live quickly, with accurate conversion tracking and attribution
• Troubleshoot tracking and implementation problems across booking engines, analytics tools, PMSs, and other hotel systems
• Develop a repeatable path from signature to first attributed booking
• Build trusted relationships with hotel owners and general managers
• Run performance conversations that are clear, credible, and commercially sharp
• Own retention and understand exactly why customers stay, expand, become at risk, or churn
• Identify at risk accounts before the customer raises their hand
• Build onboarding standards, implementation runbooks, account health scoring, communication cadences, and escalation processes
• Decide what deserves human attention and what should be automated
• Use AI aggressively to automate reporting, monitoring, follow up, customer analysis, and your own operational work
• Turn recurring customer feedback into structured Product and Engineering input
• Build the customer operations dashboard and metrics we use to run the business
• Hire and eventually lead the Customer Success and Implementation team

Who Will Be Exceptional Here

• You've owned a high-volume SMB book. You've managed many customers at once and owned outcomes (retention, activation, expansion, revenue). You know how to build leverage instead of treating every account the same.
• You're technically curious. You don't need to code, but you're comfortable in tools like Google Tag Manager and analytics — verifying events, reconciling numbers, and debugging issues before escalating.
• You're a systems operator. You spot repeat problems and turn them into documented, measurable, teachable processes. You like adding structure where little exists.
• Customers trust you. You build real relationships with owner-operators while staying commercially sharp. You can deliver hard messages clearly and leave the relationship stronger.
• You use AI as leverage. AI is already part of your workflow — analysis, automation, drafts, investigations, and follow-ups. You're excited to build a modern CS/ops function where humans + AI split the work intentionally.
• You have exceptional judgment. You know what merits a call, what should be automated, and what needs no action.
• You take extreme ownership. You proactively surface risk, follow through to outcomes, and operate with high reliability, detail, and autonomy.

This Role Is Probably Not For You If

• You want to inherit a mature Customer Success organization with established playbooks
• You primarily want to manage people rather than personally do the work
• You prefer a small portfolio of large enterprise accounts
• You think technical implementation should always be handed to Engineering
• You measure success by meetings held or tickets closed rather than customer outcomes
• You want a strategy role removed from the day to day details
• You are uncomfortable with the pace and ambiguity of an early stage company

Especially Relevant Backgrounds

There is no single perfect background for this role. We would be particularly excited by people who have worked in:

• High volume SMB Customer Success or Account Management
• Performance marketing agencies where you owned both the client relationship and tracking or implementation
• Hospitality technology
• Hotel revenue management, distribution, ecommerce, or direct booking
• Booking engines, PMSs, channel managers, or other hotel software
• Early stage startups where you helped build a function from zero to one
• Customer facing roles serving small business owners or owner operators

Why This Role Is Unusual

Most Customer Success jobs ask you to operate someone else's system. This role asks you to invent ours.

You will join early enough to decide how Autumn onboards customers, how we measure customer health, how our humans and AI divide the work, how we identify churn risk, what gets automated, what reaches Product, and eventually what the entire Customer organization looks like.

If you are exceptional, the scope should expand quickly.

The goal is not for you to remain the person manually onboarding every hotel.

The goal is for you to build a function that can serve an enormous customer base, then lead the team that runs it.

What We Offer

• Competitive cash compensation plus meaningful equity
• Significant ownership from day one
• The opportunity to build a major function from the ground up
• A path to lead Customer Success and Customer Operations as Autumn scales
• A front row seat building an AI native vertical software company in a massive industry
• Top tier medical, dental, and vision insurance
• Lunch and fitness stipend
• A beautiful private office on the Williamsburg waterfront
• A small team where exceptional people have unusually large scope and influence

Compensation & Benefits

• $130K to $180K
• Equity
• Top tier medical, dental, and vision coverage
• Lunch and fitness stipend
• Beautiful private waterfront office in Williamsburg
• Five days a week in person with a small, highly ambitious team

Location

This role is five days a week in person in Williamsburg, New York City. We believe the earliest stages of building a company are better done together.