Tailwind Insurance Systems, Inc.
Forward Deployed Engineer
Tailwind Insurance Systems, Inc., San Francisco, California, United States, 94199
About Tailwind
Tailwind is organizing the world's insurance information.
Insurance is one of the largest markets in the world, and it runs entirely on PDFs and antiquated infrastructure. We like it that way. While the industry takes years to roll out change, we ship in days.
Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.
About the Role As a Forward Deployed Engineer, you’ll sit at the intersection of engineering, product, and customer success. Owning the technical integration will be the foundation of your role — especially at first — but we expect you to evolve into leading the technical delivery of special projects and initiatives for your customers.
Your primary internal partner will be the Deployment Strategist who owns customer success overall and will partner with you to deliver value quickly and repeatedly.
This role is part solutions engineer, part product specialist, part technical consultant. You’ll develop software at the edges of our product, configure our core platform, and become the trusted technical advisor to business leaders inside our customers’ organizations.
Technical Requirements We’re looking for someone who can quickly gain context, build lightweight technical solutions, and work across teams to drive customer outcomes. You should:
Be comfortable standing up simple applications
— in a modern cloud environment (e.g., AWS, GCP, Azure), using tools like serverless functions, containerized services, or basic web frameworks. You don’t need to be a full‑stack wizard, but you should know how to go from zero to working prototype.
Have experience building and debugging data pipelines
— whether that’s writing SQL to transform and move data, scripting in Python or Java, or orchestrating lightweight ETL workflows. You’ll often need to wrangle customer data or bridge gaps between systems.
Be fluent in APIs and integration logic
— including authentication (OAuth, keys), RESTful design, and tools like Postman or curl. You’ll regularly connect Tailwind’s systems with customers’ infrastructure and tools.
Be LLM‑native
— you’re already using tools like Copilot, Claude, or ChatGPT to accelerate dev work, generate glue code, or prompt your way through hairy problems.
Thrive in ambiguity
— this isn’t a checkbox role. We’re solving problems that don’t always have clear requirements. You’ll need to think critically, get your hands dirty, and ship solutions that move the needle for customers.
What You’ll Do
Own technical integrations
for new brokerage customers — from first install to full rollout.
Expand our product
with additional integrations, analytical capabilities -- whatever there is a commercial need for that is not met by our core product
Work closely with deployment strategists and product ops
to ensure smooth rollouts and successful adoption.
Collaborate with engineering
on product fixes, light customizations, and new deployments.
Travel occasionally
for key deployments or high‑touch customers, if needed.
What Makes You a Great Fit
1–6 years in software engineering, solutions engineering, or technical consulting.
Comfortable working with APIs, SQL databases, and cloud or on‑prem deployments.
Strong communication skills — you’ll be customer‑facing and technical.
Excited to working in our SF office
Insurance or financial services 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.
Elite Team : Small, ambitious, and fast‑moving. Our core team has worked together 3 times now, hailing from Carta ($7B) and AppDirect ($2B) and includes veterans from Ramp, Apple, Salesforce and C3 AI - people who know what great product looks like, and what it takes to build it fast.
Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.
#J-18808-Ljbffr
Insurance is one of the largest markets in the world, and it runs entirely on PDFs and antiquated infrastructure. We like it that way. While the industry takes years to roll out change, we ship in days.
Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.
About the Role As a Forward Deployed Engineer, you’ll sit at the intersection of engineering, product, and customer success. Owning the technical integration will be the foundation of your role — especially at first — but we expect you to evolve into leading the technical delivery of special projects and initiatives for your customers.
Your primary internal partner will be the Deployment Strategist who owns customer success overall and will partner with you to deliver value quickly and repeatedly.
This role is part solutions engineer, part product specialist, part technical consultant. You’ll develop software at the edges of our product, configure our core platform, and become the trusted technical advisor to business leaders inside our customers’ organizations.
Technical Requirements We’re looking for someone who can quickly gain context, build lightweight technical solutions, and work across teams to drive customer outcomes. You should:
Be comfortable standing up simple applications
— in a modern cloud environment (e.g., AWS, GCP, Azure), using tools like serverless functions, containerized services, or basic web frameworks. You don’t need to be a full‑stack wizard, but you should know how to go from zero to working prototype.
Have experience building and debugging data pipelines
— whether that’s writing SQL to transform and move data, scripting in Python or Java, or orchestrating lightweight ETL workflows. You’ll often need to wrangle customer data or bridge gaps between systems.
Be fluent in APIs and integration logic
— including authentication (OAuth, keys), RESTful design, and tools like Postman or curl. You’ll regularly connect Tailwind’s systems with customers’ infrastructure and tools.
Be LLM‑native
— you’re already using tools like Copilot, Claude, or ChatGPT to accelerate dev work, generate glue code, or prompt your way through hairy problems.
Thrive in ambiguity
— this isn’t a checkbox role. We’re solving problems that don’t always have clear requirements. You’ll need to think critically, get your hands dirty, and ship solutions that move the needle for customers.
What You’ll Do
Own technical integrations
for new brokerage customers — from first install to full rollout.
Expand our product
with additional integrations, analytical capabilities -- whatever there is a commercial need for that is not met by our core product
Work closely with deployment strategists and product ops
to ensure smooth rollouts and successful adoption.
Collaborate with engineering
on product fixes, light customizations, and new deployments.
Travel occasionally
for key deployments or high‑touch customers, if needed.
What Makes You a Great Fit
1–6 years in software engineering, solutions engineering, or technical consulting.
Comfortable working with APIs, SQL databases, and cloud or on‑prem deployments.
Strong communication skills — you’ll be customer‑facing and technical.
Excited to working in our SF office
Insurance or financial services 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.
Elite Team : Small, ambitious, and fast‑moving. Our core team has worked together 3 times now, hailing from Carta ($7B) and AppDirect ($2B) and includes veterans from Ramp, Apple, Salesforce and C3 AI - people who know what great product looks like, and what it takes to build it fast.
Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.
#J-18808-Ljbffr