Customer Enablement Lead, Legal AI
Top Benefits
About the role
About us
Walter’s AI Agent helps busy law firms stop moving information manually across many fragmented tools. Our platform brings document drafting, email drafting, document generation and review, and knowledge-driven workflows into a single, lawyer-friendly experience so legal teams can do higher-value work faster. Walter integrates with systems lawyers rely on, including Outlook and document management platforms like iManage, to make drafting, blacklines and document workflows dramatically more efficient.
Join Walter at a real inflection point. We are early and shipping fast for major law firms. The work is ambitious, the bar is high, and you will have room to grow. We move quickly, take ownership, and stay close to customers across the team. If you thrive in ambiguity, push for excellence, and want to shape the future of legal work, come build with us.
Role overview
The Legal AI Enablement Lead helps law firms put Walter to work in real matters. Make adoption straightforward with clear materials and training, prove what works with hands on customer work, then package the learnings so others can repeat the results. Partner closely with Product and Engineering, surfacing customer insights that shape the product roadmap. Promote safe, responsible use so firms can scale with confidence.
What you'll do
- Map common workflows and help our customers build clear, practice-specific playbooks with prompts, inputs, and example outputs.
- Plan and deliver onboarding programs, office hours, cohort trainings, and short walkthrough videos that help lawyers get started.
- Run forward deployed rotations with select enterprise firms, embedded with users, tuning playbooks to real matters, and removing blockers.
- Build and own adoption success metrics (adoption rates, utilization, cohort metrics, health scores) to maximize customer ROI.
- Maintain the Help Center, publish articles, and keep materials current as the product evolves.
- Triage issues in Intercom and email, reproduce bugs with clear steps and context, and coordinate with Engineering.
- Capture and synthesize customer feedback. Write clear improvement proposals with examples and expected impact. Close the loop with customers after releases.
- Work with firm leads on privacy, security, and safe use guidelines ahead of wider rollout.
- Keep customer notes organized and share concise weekly updates with the team.
Requirements
- 3 to 7 years in a law firm or ALSP, such as associate, KM, innovation, paralegal or legal ops.
- Can translate partner expectations into step-by-step process.
- Strong writing and teaching chops. Comfortable on camera for 3 to 7 minute videos.
- Knows prompt design basics, evaluation tactics, and risk controls for LLMs.
- Startup bias to action. Ships messy v1, measures, iterates. And loves spending a day helping lawyers write playbooks.
- Time zone alignment with EST preferred.
Nice-to-Haves
- Transactional law exposure
- Experience with iManage or other DMS systems
- Microsoft Word and Outlook power user knowledge
- Familiarity with Intercom or similar
- Prior enablement, solutions, or forward deployed work in a startup
- Experience working directly with founders or visionary leaders in startups or high-growth environments
- Experience in legal tech, fintech, or a similarly complex domain
- Strong interest in legal tech and its potential to transform the industry
What we offer
- An opportunity to play a key role in executing a bold vision for the future of legal tech
- Competitive salary plus equity
- Flexible remote work in Canada
- Extended health benefits
- 3 weeks of paid vacation
Equal opportunity employer
At Walter, we are committed to providing equal employment opportunities to all individuals, regardless of background, and fostering a workplace that values diversity, equity, and inclusion. We actively encourage candidates from underrepresented backgrounds to apply, as a diverse team enriches our culture and drives innovation.
If you are a motivated individual with a passion for learning and a desire to contribute to a fast-paced startup environment, we encourage you to apply!
How to apply
Submit an application here by
November 16, 2025
: https://forms.gle/FgrNoh9T579jR1Lq7
Compensation
$140,000-$180,000
About Walter
Walter enables modern, collaborative relationships between law firms and their clients. Our software platform dramatically and immediately reduces the unbillable, frustrating tasks across law firms so legal teams can focus on higher-value billable work. But it’s also transformative for their clients. They get on-demand digital access to their data so they can collaborate with their law firm on everything from executing private financings to managing their cap tables – and beyond. In a time when software companies are inserting themselves between law firms and their clients, and AI threatens to disrupt everything, Walter is the modern software platform law firms need to grow.
Customer Enablement Lead, Legal AI
Top Benefits
About the role
About us
Walter’s AI Agent helps busy law firms stop moving information manually across many fragmented tools. Our platform brings document drafting, email drafting, document generation and review, and knowledge-driven workflows into a single, lawyer-friendly experience so legal teams can do higher-value work faster. Walter integrates with systems lawyers rely on, including Outlook and document management platforms like iManage, to make drafting, blacklines and document workflows dramatically more efficient.
Join Walter at a real inflection point. We are early and shipping fast for major law firms. The work is ambitious, the bar is high, and you will have room to grow. We move quickly, take ownership, and stay close to customers across the team. If you thrive in ambiguity, push for excellence, and want to shape the future of legal work, come build with us.
Role overview
The Legal AI Enablement Lead helps law firms put Walter to work in real matters. Make adoption straightforward with clear materials and training, prove what works with hands on customer work, then package the learnings so others can repeat the results. Partner closely with Product and Engineering, surfacing customer insights that shape the product roadmap. Promote safe, responsible use so firms can scale with confidence.
What you'll do
- Map common workflows and help our customers build clear, practice-specific playbooks with prompts, inputs, and example outputs.
- Plan and deliver onboarding programs, office hours, cohort trainings, and short walkthrough videos that help lawyers get started.
- Run forward deployed rotations with select enterprise firms, embedded with users, tuning playbooks to real matters, and removing blockers.
- Build and own adoption success metrics (adoption rates, utilization, cohort metrics, health scores) to maximize customer ROI.
- Maintain the Help Center, publish articles, and keep materials current as the product evolves.
- Triage issues in Intercom and email, reproduce bugs with clear steps and context, and coordinate with Engineering.
- Capture and synthesize customer feedback. Write clear improvement proposals with examples and expected impact. Close the loop with customers after releases.
- Work with firm leads on privacy, security, and safe use guidelines ahead of wider rollout.
- Keep customer notes organized and share concise weekly updates with the team.
Requirements
- 3 to 7 years in a law firm or ALSP, such as associate, KM, innovation, paralegal or legal ops.
- Can translate partner expectations into step-by-step process.
- Strong writing and teaching chops. Comfortable on camera for 3 to 7 minute videos.
- Knows prompt design basics, evaluation tactics, and risk controls for LLMs.
- Startup bias to action. Ships messy v1, measures, iterates. And loves spending a day helping lawyers write playbooks.
- Time zone alignment with EST preferred.
Nice-to-Haves
- Transactional law exposure
- Experience with iManage or other DMS systems
- Microsoft Word and Outlook power user knowledge
- Familiarity with Intercom or similar
- Prior enablement, solutions, or forward deployed work in a startup
- Experience working directly with founders or visionary leaders in startups or high-growth environments
- Experience in legal tech, fintech, or a similarly complex domain
- Strong interest in legal tech and its potential to transform the industry
What we offer
- An opportunity to play a key role in executing a bold vision for the future of legal tech
- Competitive salary plus equity
- Flexible remote work in Canada
- Extended health benefits
- 3 weeks of paid vacation
Equal opportunity employer
At Walter, we are committed to providing equal employment opportunities to all individuals, regardless of background, and fostering a workplace that values diversity, equity, and inclusion. We actively encourage candidates from underrepresented backgrounds to apply, as a diverse team enriches our culture and drives innovation.
If you are a motivated individual with a passion for learning and a desire to contribute to a fast-paced startup environment, we encourage you to apply!
How to apply
Submit an application here by
November 16, 2025
: https://forms.gle/FgrNoh9T579jR1Lq7
Compensation
$140,000-$180,000
About Walter
Walter enables modern, collaborative relationships between law firms and their clients. Our software platform dramatically and immediately reduces the unbillable, frustrating tasks across law firms so legal teams can focus on higher-value billable work. But it’s also transformative for their clients. They get on-demand digital access to their data so they can collaborate with their law firm on everything from executing private financings to managing their cap tables – and beyond. In a time when software companies are inserting themselves between law firms and their clients, and AI threatens to disrupt everything, Walter is the modern software platform law firms need to grow.