Gusto

Forward Deployed Engineer

Gusto$110K — $120K *
Legal & Accounting
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 1-3 years in sales, customer success, or solutions engineering at a B2B software company (legal tech preferred)
  • Experience in a law firm environment or familiarity with legal workflows
  • Self-starter with a capacity for navigating ambiguity
  • Strong technical curiosity and capability to learn software quickly
  • Understanding of AI tools and their application in legal practices
  • Consultative mindset to effectively diagnose and prescribe customer solutions
  • Excellent communication skills for diverse audiences
  • Willingness to travel extensively (50-70%) across various locations.

Responsibilities

  • Embed with customers to assess workflows and identify pain points
  • Design and implement tailored solutions on the CaseMark and case.dev platforms
  • Advise law firm leadership on optimizing workflows with AI
  • Travel frequently to customer sites to drive adoption and measure ROI
  • Act as a feedback conduit between customers and product teams
  • Develop training materials and frameworks for scalability
  • Foster relationships with decision-makers in law firms.

Benefits

  • Competitive compensation and equity options
  • Travel expenses fully covered with additional travel benefits
  • Opportunity to build a strong resume as an AI adoption expert in legal
  • Directly influence product development with customer insights
  • Career acceleration in a high-impact role at a fast-growing startup
  • Networking opportunities with top law firms and legal organizations.
Full Job Description
Embed with leading law firms to implement AI solutions on-site (50-70% travel), gathering critical customer insights that directly shape product development at a fast-growing legal AI startup.

Description

We're building CaseMark: an AI-native legal platform with 700+ discrete "easy buttons" that solve specific legal tasks. We need a Forward Deployed Engineer to embed with our largest customers and turn platform capabilities into transformative firm-wide workflows.

This is one of the most critical new roles at CaseMark. You'll be our eyes and ears in the field-working directly with law firms and legal service providers to implement solutions on the CaseMark and case.dev platforms while feeding invaluable customer insights back to our product team. This role is perfect for someone early in their career who wants to build an impressive resume and network at the intersection of AI and legal tech.

What You'll Do
  • Embed with our largest customers (law firms, court reporting companies, legal tech partners) to understand their workflows, pain points, and opportunities.
  • Work hands-on with the CaseMark and case.dev platforms to design and implement custom solutions: configuring workflows, building worker agents, creating tabular analysis processes, and training teams on AI-native legal work.
  • Act as trusted advisor to firm leadership, practice groups, and legal ops teams-showing them how to reorganize workflows around AI.
  • Travel frequently (50-70%) to customer sites domestically and internationally, spending days or weeks embedded with teams to drive adoption and prove ROI.
  • Serve as the critical feedback loop between customers and product: gather insights from embedded work, identify product gaps and opportunities, and translate customer needs into actionable product requirements.
  • Create repeatable playbooks, training materials, and implementation frameworks that scale across customers.
  • Build deep relationships with decision-makers at leading law firms and legal organizations-creating a powerful professional network.


What We're Looking For
  • 1-3 years in sales, customer success, or solutions engineering at a B2B software company (legal tech strongly preferred).
  • Legal industry exposure: worked at a law firm, sold to law firms, grew up around lawyers, or deep familiarity with how legal work actually happens.
  • Self-starter mentality: you thrive with autonomy, ambiguity, and the responsibility of being the expert in the room.
  • Technical curiosity: you don't need to code, but you can learn software quickly, configure complex systems, and explain technical concepts to non-technical users.
  • AI-native mindset: you understand how AI tools work and can envision how they transform workflows.
  • Consultative approach: you know how to listen, diagnose problems, and prescribe solutions that customers actually adopt.
  • Exceptional communication skills: you can present to partners, train paralegals, and earn trust across all levels of a firm.
  • Willingness to travel extensively (50-70% of time) domestically and internationally to accommodate customer needs.
  • Based in San Francisco, New York, or London (we're hiring in all three markets).


Why Join
  • Competitive compensation + equity:
  • San Francisco: $110-120K + equity
  • New York: $115-125K + equity
  • London: £70-80K + equity
  • All travel expenses covered + travel perks


  • Build an exceptional resume: you'll become a recognized expert on AI adoption in law firms-one of the most valuable skillsets as the legal industry transforms.
  • Create a powerful network: work directly with leadership at top law firms, court reporting companies, and legal tech organizations.
  • Shape product development: your embedded customer feedback will directly influence the CaseMark and case.dev roadmaps.
  • Career acceleration: this is a high-visibility, high-impact role where your work transforms how legal professionals practice law.
  • Join a fast-moving startup backed by top investors where you'll learn from the ground up how to scale AI products.


Location & Travel Expectations This role requires frequent travel (50-70%) to customer sites across the US and internationally. We're hiring in three markets:
  • San Francisco (primary hub)
  • New York
  • London


Expect to spend 2-4 days per week embedded with customers, with some weeks requiring full-week engagements. Home base will be in your respective city.

About Gusto

Gusto is a cloud-based human resources software platform that provides payroll, benefits, and HR management services to small businesses. The company was founded in 2011 and is headquartered in San Francisco, California. Gusto's platform automates many of the administrative tasks associated with HR, such as payroll processing, tax filings, and benefits administration. The company also offers a range of HR services, including compliance support, employee onboarding, and time tracking. Gusto is committed to helping small businesses succeed by providing them with the tools and resources they need to manage their HR operations more efficiently.
Learn more about Gusto
Size
1,000 employees
Industry
Founded
2012

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