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Customer Success Lead

Customer SuccessRemoteFull-time

Why this role

Corporate teams do not just sign up and figure it out. They need a partner who understands their brand, their compliance requirements, and their goals. This role is the bridge between FlyingToast and the companies that rely on it. You'll own the entire post-sale journey: onboarding, training, adoption, expansion, and retention. You are building the customer success function from the ground up.

What you'll do

  • Own enterprise onboarding: brand setup, voice training, platform connection, first publish
  • Develop playbooks and documentation for self-service and guided onboarding paths
  • Build ongoing relationships with key accounts and drive product adoption
  • Surface product feedback and feature requests to the product team with business context
  • Monitor account health metrics and proactively address churn risk
  • Build processes and tooling that scale as the customer base grows from 0 to 100+

What we're looking for

  • 3+ years in customer success or account management at a B2B SaaS company
  • Experience with enterprise clients, ideally in regulated industries
  • Strong communication skills. You can explain AI concepts to non-technical stakeholders.
  • Comfort with ambiguity. You will be defining the customer success function, not inheriting one.
  • Technical curiosity and interest in how the product works under the hood

Nice to have

  • Experience with AI-powered products and explaining AI capabilities/limitations to users
  • Background in social media marketing or content operations
  • Familiarity with customer success platforms (Vitally, Gainsight, or similar)

What success looks like

In your first 6 months...

  • Onboarding time-to-value (first published post) is under 48 hours for guided accounts
  • Net retention rate is above 100% because existing customers are expanding, not churning
  • You've built a self-service knowledge base that reduces support volume for common questions

Compensation

$100,000-$140,000/year

ABOUT US

About FlyingToast

FlyingToast is an AI-powered social media platform for business teams. We help companies in law, finance, healthcare, consulting, and tech generate on-brand social content and publish it across 13+ platforms. We're early-stage and building quickly, so every role is close to the product, customers, and technical decisions.

BENEFITS

Benefits & perks

Remote-first

Work from anywhere with a schedule that fits focused work

Flexible hours

Async by default, with meetings only when they help

Real ownership

Own meaningful projects from idea to shipped product

Learning support

Books, courses, and tools when they help you do the job better

Work setup

We'll help you get the core equipment you need

Flexible time off

Take time off with clear planning and handoffs

VALUES

Our values

Ship fast, learn faster

We ship in small steps, learn from real usage, and keep momentum without lowering the bar.

Practical AI

AI is central to the product, but the standard is usefulness: reliable workflows, strong brand fit, and clear user control.

Quality over quantity

Our customers need work they can trust. We care about reliability, clarity, and details that make the product feel dependable.

Ownership, not tasks

You own outcomes, not task lists. We expect people to make decisions, explain tradeoffs, and improve the work around them.

CULTURE

How we work

  • Async-first, small distributed team across multiple time zones
  • High ownership, low meeting load
  • Modern tooling and a Laravel/Vue codebase that moves quickly
  • Short feedback loops with regular product reviews

APPLY

Apply for this role

Customer Success Lead

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