Demo

Director of Customer Success

Greenshoe
Chicago, IL Full Time
POSTED ON 9/29/2025
AVAILABLE BEFORE 1/26/2026

Location: Chicago, IL - Hybrid (West Loop)

Role: Full-time, early team

Comp: $80,000 - $95,000 equity


About Greenshoe

Greenshoe is building the AI-native future of corporate disclosure. We help law firms and public companies prepare SEC filings with superhuman speed and precision. Major law firms call us a “cheat code” and we’ve raised a substantial seed round of funding and now we’re sprinting to become the market standard.


We’re an experienced team of lawyers and scientists building frontier software – and we’re having fun doing it. We’re looking for someone sharp, curious, and proactive to help supercharge our go-to-market engine.You will own the customer experience, develop trusted advisor relationships, and drive adoption, engagement, and retention.


Why this is unique

  • Founder-led sales: You’ll work directly with our CEO, who’s still closing every deal.
  • Deep RegTech space: Learn the multibillion-dollar world of capital markets from the ground up.
  • Hybrid Role: You’ll have the opportunity to help build out our sales operations and ensure that we’re building what we need for our clients.


What you’ll do

  • Serve as the primary point of contact and trusted advisor for an assigned book of customers
  • Create and execute onboarding and training plans tailored to each customer's needs
  • Conduct regular business review meetings, identify and develop expansion opportunities
  • Analyze usage data to understand engagement, diagnose risks, and proactively solve issues
  • Collect customer feedback and act as the internal voice of the customer to Product and
  • Executives
  • Drive renewal, expansion, and customer advocacy by ensuring measurable value realization
  • Test new GTM tools, help with and security reviews, conferences, and customer case studies.
  • Support CEO through entirety of sales cycle, adding value by identifying win opportunities.
  • Incorporate AI tools into all of the above.


You’re perfect for this if you…

  • Want to be close to both customers – building relationships and building systems.
  • Communicate clearly and write crisp, friendly emails.
  • Are super organized. 
  • Love learning complex industries (SEC rules, law firm workflows) and can explain them simply.
  • Are proactive. If you see something broken or confusing, you fix it or figure it out.


Must-haves

  • 3 year in an ops, legal, finance, research, consulting, or startup environment.
  • Strong written and verbal communication abilities
  • A consultative approach focused on value realization and outcome delivery
  • Experience crafting and executing success plans based on customer goals
  • Analytical and reporting skills to synthesize data into compelling insights
  • Self-motivated problem solver comfortable dealing with ambiguity
  • Passion for understanding customer needs and promoting their success
  • Great with ChatGPT, Perplexity or similar AI-based research and productivity tools. 
  • Authorized to work in the U.S.


What you’ll get

  • Competitive salary equity.
  • A front-row seat to building the GTM playbook with the founding team.
  • The tech stack, gear, and tools you need.


Interested?

Email payton@greenshoe.ai your LinkedIn and a cover letter or Loom video that covers three things:

o   (i) What interested you in Greenshoe?

o   (ii) How have you used AI in your day to day?

o   (iii) Share any relevant experience you had in previous jobs that would help you nail this one. Be as specific as possible.


Salary : $80,000 - $95,000

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