Deployment Engineer

About Tailwind

Tailwind is rebuilding the infrastructure behind commercial insurance.

It’s one of the biggest industries in the world— and it still runs on antique infrastructure and processes. We like it that way. While legacy players take years to roll out change, we ship in days.

If you want high agency, zero bureaucracy, and a chance to fix something that actually matters, come talk to us.

About the Role

As a Deployments Engineer, you’ll sit at the intersection of engineering, product, and customer success — owning the technical onboarding and deployment experience for new brokerages.

This is a forward-deployed role: part solutions engineer, part product specialist, part technical consultant. You’ll work directly with broker customers to integrate Tailwind into their workflows, deploy new product features, and ensure smooth adoption across the brokerage.

You’ll also bring feedback from the field back to engineering and product to help shape our roadmap.

What You’ll Do

• 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 (if needed) for key deployments or high-touch customers.

What Makes You a Great Fit

• 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.

Why You Should Work Here

• Impact: You’ll be the bridge between product and customer — ensuring success at the most critical stage of adoption. The best startups are adopting this model because it gives engineers direct exposure to customers, influence over the roadmap, and a faster feedback loop than traditional engineering roles. Skills in this area are in high demand and open doors to product, leadership, and founder paths.

• Speed: Work closely with engineering to ship improvements fast.

• Career growth: Forward-deployed engineers often move into product, solutions architecture, or technical leadership as startups scale.

• Team: Small, ambitious, and fast-moving, with experience at Ramp, Carta, C3 AI, and more.