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.

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.

• 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…