Deployment Strategist
About Tailwind
We’re 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. There's a huge market opportunity, and we plan to capture it.
One of our strengths is speed. In an industry where implementations are measured in years, we like to deliver value in weeks. 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.
About the Role
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, but recent history suggests that this will not be common (< 10%).
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.
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 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
Work with a hyper talented team, ⅔ of which have been a part of winning teams at Carta,C3 AI, AppDirect, and Ramp
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