Tailwind Insurance Systems, Inc.
Deployment Strategist
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 We’re a tight-knit team moving fast — the kind of place where you’ll work directly with leadership, wear many hats, and see your ideas in production fast.
As a Deployments Strategist you’ll work at our office in San Francisco and own the journey from “signed customer” to “confident daily user.” You’ll design and execute onboarding plans, run kickoff and training sessions, and create resources that make adoption fast and effortless. You may need to travel to customers from time‑to‑time ( There’s also an opportunity to leverage your technical skills to deliver project based work for our customers that want to get more value out of the dataset we help them build and maintain. So if you have technical aptitude or experience (SQL, python, LLMs) then there’s room to grow into that function as well, but strictly speaking technical experience is not required for this role as you’ll be paired with a Forward Deployed Engineer (see that role here).
A great candidate will be someone who loves creating order out of ambiguity and making customers feel like they’re in great hands.
What You’ll Do
Lead onboarding projects for new customers, ensuring timely and successful product adoption
Run engaging kickoff calls, training sessions, and Q&A meetings
Identify opportunities to partner with customers to deliver new product or project based consulting engagements
Build and maintain onboarding materials: playbooks, quick start guides, how‑to videos, and FAQs
Track progress against onboarding milestones and proactively address roadblocks
Partner closely with forward deplored engineering, sales, product, and support to ensure a seamless handoff and customer experience
What Makes You a Great Fit
3–5 years of work experience in consulting, or in customer facing roles at a SaaS company
Experience juggling multiple deployments/projects at once
Exceptional written and verbal communication skills — you can make complex concepts easy to understand
Comfort operating in a fast‑changing, resource‑constrained startup environment
Empathy for customers combined with a bias toward action
Bonus points for:
Strong blend of technical aptitude (comfortable with product configuration, data workflows, and basic troubleshooting) and commercial acumen (understanding customer business goals and how they tie to ROI).
Creating enablement resources (guides, videos, templates)
Why You Should Work Here
Direct impact on customer satisfaction and retention
There are 2 ingredients to achieving high growth in your career; be great at your job, be a part of a fast growing company. We have one of those, the other is up to you.
Opportunity to see how the latest AI is being applied to solve high value problems
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
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
We’re in‑person at our beautiful offices 5 days per week in San Francisco (financial district). If you want to do the most meaningful work of your career, with an elite team, in a trillion dollar market, come join us!
#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 We’re a tight-knit team moving fast — the kind of place where you’ll work directly with leadership, wear many hats, and see your ideas in production fast.
As a Deployments Strategist you’ll work at our office in San Francisco and own the journey from “signed customer” to “confident daily user.” You’ll design and execute onboarding plans, run kickoff and training sessions, and create resources that make adoption fast and effortless. You may need to travel to customers from time‑to‑time ( There’s also an opportunity to leverage your technical skills to deliver project based work for our customers that want to get more value out of the dataset we help them build and maintain. So if you have technical aptitude or experience (SQL, python, LLMs) then there’s room to grow into that function as well, but strictly speaking technical experience is not required for this role as you’ll be paired with a Forward Deployed Engineer (see that role here).
A great candidate will be someone who loves creating order out of ambiguity and making customers feel like they’re in great hands.
What You’ll Do
Lead onboarding projects for new customers, ensuring timely and successful product adoption
Run engaging kickoff calls, training sessions, and Q&A meetings
Identify opportunities to partner with customers to deliver new product or project based consulting engagements
Build and maintain onboarding materials: playbooks, quick start guides, how‑to videos, and FAQs
Track progress against onboarding milestones and proactively address roadblocks
Partner closely with forward deplored engineering, sales, product, and support to ensure a seamless handoff and customer experience
What Makes You a Great Fit
3–5 years of work experience in consulting, or in customer facing roles at a SaaS company
Experience juggling multiple deployments/projects at once
Exceptional written and verbal communication skills — you can make complex concepts easy to understand
Comfort operating in a fast‑changing, resource‑constrained startup environment
Empathy for customers combined with a bias toward action
Bonus points for:
Strong blend of technical aptitude (comfortable with product configuration, data workflows, and basic troubleshooting) and commercial acumen (understanding customer business goals and how they tie to ROI).
Creating enablement resources (guides, videos, templates)
Why You Should Work Here
Direct impact on customer satisfaction and retention
There are 2 ingredients to achieving high growth in your career; be great at your job, be a part of a fast growing company. We have one of those, the other is up to you.
Opportunity to see how the latest AI is being applied to solve high value problems
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
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
We’re in‑person at our beautiful offices 5 days per week in San Francisco (financial district). If you want to do the most meaningful work of your career, with an elite team, in a trillion dollar market, come join us!
#J-18808-Ljbffr