Head of Operations

Anecdote is building the world’s most trusted travel concierge.

We make travel planning seamless and stress-free — not by replacing people with AI, but by using AI to give superpowers to a world-class human concierge team who actually cares. We're leading a renaissance in customer care. Our hybrid approach pairs travelers with real human concierges who bring empathy, charisma, judgment, intuition, and taste — supported by thoughtfully-designed AI tools that help them move faster and smarter than traditional travel agents.

Customers trust us with their life’s most memorable trips and have called us their “highest NPS experience in a decade.”

Today, we focus on hotels. Travelers text us, get matched with a concierge, and receive curated options, VIP perks, and real-time support. We’ve handled hundreds of hotel stays and are scaling to thousands this year, and millions beyond that as we become the definitively high-trust, high-touch way to travel. Long term, we’re building a full stack travel platform: end-to-end, expert-planned trips that work seamlessly because they’re designed by people who truly know the traveler and fit all the puzzle pieces together perfectly.

We’re an ops-heavy, service-obsessed team. In a world being rapidly enshittified by companies cutting corners and treating customer service as a cost center,
we believe great service is a value proposition and a competitive advantage unto itself
. Our partners at XYZ Venture Capital (recently Midas-listed) and OVO Fund share that conviction, and we’re looking for a Head of Ops who’s excited to pioneer how to scale great service to the world.

• The role is in-person in NYC with some WFH allowed.
• This is a COO/C-Suite track role.
• Compensation Range
  : $160k-$200k salary + 1.4-2% equity (4 year vest, 1 year cliff)

• Lead and grow our concierge team
  :
  Our concierges aren’t just call center operators reading off a script; they’re high agency, charismatic, and hyper-competent travel experts. You’ll be across every aspect of this team, from hiring to training/coaching to setting quality standards. Our team currently has 4 concierges, and we expect to double this by EoY.
• Assist concierges with customers
  :
  Unlike a traditional ops role, this role will be partially customer-facing, especially in the beginning. You’ll start off chatting with customers directly alongside our concierge team, and transition more to supervising and quality control as the team becomes more autonomous.
• Refine and own day-to-day ops
  :
  You’re in charge of building our ops engine by building repeatable processes to help us achieve travel industry firsts like deep travel personalization and sub-60 second human response times.
• Partner with our engineering team
  :
  Anecdote’s road to scale involves process, training, and tech. While you’ll be handling the first two directly, you’ll work with our eng team to shape AI tools that genuinely enhance our concierges’ workflows.

• You’re a top 1% talent in operations management, customer experience/success, or similar ops-heavy and/or people-facing leadership roles.
• You’ve successfully built or led teams before, ideally a frontline service team or ops team.
• You’ve got 5+ years of work experience in general. You've been around the block and have the war stories to prove it.
• You’re a skilled systems thinker, able to learn the ropes quickly, analyze what needs fixing, and execute a fix.
• You’re able to communicate effectively with both customers and internal team members.
• You’re highly organized and detail-oriented, and the double spaces in this sentence made you physically cringe.

• You’re a high empathy individual who’s great at perspective taking and thinking about how others experience things. If friends call you a great listener and rely on your sage advice, or you’re the one always hosting the dinner parties, you’ll be right at home here.
• You’re not afraid to roll up your sleeves and get in the weeds. You know that doing anything great involves 20% insight and 80% hard work.
• You’re convinced the ultimate use of today’s transformative GenAI technology cannot possibly be AI slop…