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Deployment Engineer

Tailwind is rebuilding the infrastructure behind commercial insurance.
DevOps
Entry-Level Software Engineer
In-Person
1+ year of experience
Finance · Enterprise SaaS

Job Description

Tailwind is revolutionizing the commercial insurance industry by rebuilding its infrastructure from the ground up. As a Deployment Engineer, you'll play a crucial role at the intersection of engineering, product, and customer success. This forward-deployed position combines solutions engineering, product specialization, and technical consulting.

You'll be responsible for owning the technical onboarding and deployment experience for new brokerages, working directly with broker customers to integrate Tailwind into their workflows. The role involves configuring integrations, managing automation settings, and ensuring smooth product adoption across brokerages. You'll also have the unique opportunity to influence product development by bringing valuable field feedback to the engineering and product teams.

The position offers significant impact as you'll be the bridge between product and customers, ensuring success at critical adoption stages. Working with a small, ambitious team with experience from companies like Ramp, Carta, and C3 AI, you'll have the opportunity to ship improvements quickly and grow into product, solutions architecture, or technical leadership roles as the company scales.

This role is perfect for someone with 1-4 years of experience in software engineering or technical consulting, who is comfortable with APIs and basic scripting, and excels at both technical problem-solving and customer communication. While insurance or fintech experience is beneficial, it's not required. The position offers high agency, zero bureaucracy, and the chance to make a meaningful impact in a major industry that's ripe for transformation.

Last updated 3 days ago

Responsibilities For Deployment Engineer

  • Own technical onboarding for new brokerage customers — from first install to full rollout
  • Configure integrations, workflows, and automation settings for each customer's needs
  • Collaborate with engineering on product fixes, customizations, and new deployments
  • Partner with customer success and product ops to ensure smooth rollout and adoption
  • Gather customer feedback to inform product improvements and roadmap priorities
  • Build and maintain internal deployment playbooks for speed and repeatability
  • Occasionally travel onsite for key deployments or high-touch customers

Requirements For Deployment Engineer

JavaScript
Python
  • 1–4 years in software engineering, solutions engineering, or technical consulting
  • Comfort with APIs, integrations, and basic scripting (JavaScript, Python, or similar)
  • Strong communication skills — you'll be customer-facing and technical
  • Problem solver: able to debug workflows, integrations, and data pipelines in real time
  • Startup-ready: you thrive in ambiguity and like wearing multiple hats
  • Insurance or fintech experience a plus but not required

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