Founding CSM

Tailwind Insurance Systems

$120K — $150K *
Consumer Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2-4+ years in a customer-facing role at a B2B SaaS company
  • Experience in building or enhancing onboarding/activation programs
  • Strong written and verbal communication skills
  • Ability to work well in ambiguous situations
  • Experience collaborating with product and engineering teams
  • Interest in AI and its impact on workflows

Responsibilities

  • Own new customer experiences from contract signature to full activation
  • Build and continuously improve the onboarding playbook
  • Define and measure activation criteria for different customer types
  • Capture customer feedback and collaborate with product on prioritization
  • Solve customer problems effectively to prevent recurrence

Benefits

  • High ownership over customer experiences
  • Opportunities to work directly with founders
  • Dynamic role shaping the customer onboarding process
  • Collaborative environment with product and engineering teams
  • Focus on learning and adapting in fast-paced scenarios
Full Job Description
About the Role

This is a high-ownership, customer-facing role. You'll work directly with founders, and own how new customers experience Tailwind from the moment they sign through the point they're fully activated.

You'll be one of the faces of Tailwind through onboarding. You'll lead onboardings, building training, and defining what "activated" actually means for each customer. You'll also run the loop back into product, turning what customers are asking for into prioritized signal the team can act on.

We're looking for someone sharp, charismatic, and customer-obsessed- someone who can hold a room, write something a customer actually reads, and ship a v1 of the playbook this week instead of speccing the perfect one for a month.

What You'll Do
  • Own how new customers experience Tailwind from contract signature to full activation
  • Build the onboarding playbook- kickoff materials, training, live sessions, in-app guides, and rebuild it as we learn what works
  • Define what "activated" means for different customer types, measure it, and improve it over time
  • Run the feedback loop back into product: capture what customers ask for, find the patterns, and partner with product to prioritize what ships next
  • Be a force multiplier- every customer problem you solve should stay solved
What Makes You a Great Fit
  • 2-4+ years in a customer-facing role at a B2B SaaS company (CSM, onboarding, implementation, solutions, training, devrel, etc.)
  • You've built or meaningfully improved an onboarding or activation program - not just executed someone else's
  • Strong written and verbal communication - charismatic on camera, sharp on the page
  • Comfortable with ambiguity and energized by figuring things out as you go
  • Experience collaborating with product and engineering to turn customer signal into shipped features
  • Interest in AI and how it's reshaping modern workflows (hands-on experience is great, but not required)

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