Enterprise Account Executive

DraftWise is a leading AI company in the legal industry, developing a secure knowledge platform for elite law firms. Their product helps lawyers draft, negotiate, and review contracts faster by leveraging historic legal contracts with data management, machine learning, and language analytics. The company has achieved product-market fit, is backed by Y-Combinator and Index Ventures, and is growing rapidly. The Enterprise Account Executive will manage strategic law firm accounts, driving new business and expansion through complex sales cycles, building relationships with senior stakeholders, and developing tailored solutions.

Must Have

• Own the full sales cycle for large / global law firms
• Develop and execute strategic account plans for named enterprise accounts
• Drive expansion of existing customers from initial land to multi-year agreements
• Build trusted advisor relationships with partners, practice group leaders, C-suite, KM, Innovation, and IT stakeholders
• Orchestrate internal and external stakeholders through long, complex buying cycles
• Lead executive-level conversations that tie DraftWise to firm-wide initiatives
• Deeply understand each firm’s workflows, tech stack, and knowledge management challenges
• Run structured discovery to uncover business pain, value drivers, and success metrics
• Partner with Product and Customer Success to design and position tailored solutions, pilots, and roll-out plans
• Own pricing, proposal development, and commercial negotiations for enterprise-level contracts
• Build clear business cases and ROI narratives
• Consistently meet or exceed quarterly and annual new ARR and expansion targets
• Partner closely with Marketing on campaigns, events, and ABM programs
• Collaborate with Product and Engineering to relay customer feedback and influence roadmap priorities
• Work with Customer Success to ensure smooth handoffs, successful implementations, and expansion opportunities
• Stay on top of legal tech trends, competitive landscape, and emerging needs of top-tier firms
• Maintain accurate and up-to-date pipeline, forecasting, and activity data in CRM and sales tools
• Share structured insights from the field to help shape GTM strategy, pricing, and positioning
• 7+ years in B2B SaaS sales, with enterprise or mid-market/enterprise hybrid roles
• Proven success meeting or exceeding quota, closing complex deals, and expanding within existing accounts
• Demonstrated ability to navigate multi-stakeholder, multi-threaded sales cycles
• Understanding of the legal industry, professional services, or knowledge-intensive environments
• Excellent verbal and written communication skills
• Strong interpersonal skills and executive presence
• Skilled at discovery, needs analysis, and building compelling value/ROI narratives
• Comfortable with modern sales and productivity tools (Salesforce, Salesloft, Gong, LinkedIn Sales Navigator, Apollo)
• Entrepreneurial, curious, and resourceful with a strong growth mindset

Good to Have

• Experience selling into law firms or JD is a strong plus

Perks & Benefits

• Compensation: $300k+ OTE
• Equity plan
• Competitive salary
• Private medical care
• New laptop
• Generous PTO / sick leave
• Opportunity to lead our company as we disrupt the legal world

About Draftwise

DraftWise is at the forefront of AI in the legal industry, building a secure knowledge platform that helps lawyers at elite law firms draft, negotiate and review contracts faster, and with an edge over their competitors. Our core product unlocks for the first time the years of historic legal contracts that firms have negotiated for their clients. We use the latest in data management, machine learning and language analytics to help lawyers and legal professionals write better, safer contracts. Some reasons to join DraftWise:

• Our core offering has achieved product market fit proven by our partnerships with the industries leading Vault 10, Magic Circle and AMLAW 100 firms.
• Our founding team is composed of former Palantir and Google engineers along with an experienced lawyer from a top global law firm.
• We are backed by Y-Combinator and recently raised our $20M in our Series A backed by Index Ventures
• We are a fully remote company, though offer the option to co-work in our major cities in the US and Europe.
• We are working with the latest generative AI technology and developing practical applications of it for the legal industry
• We are solving problems that matter to lawyers, and our users love us for it!

About the role

About DraftWise

DraftWise is building an innovative knowledge platform for the legal industry. Our core product unlocks for the first time the years of historic legal contracts that firms have negotiated for their clients. We use the latest in data management, machine learning and language analytics to help lawyers and legal professionals write better, safer contracts.

Our founding team is composed of former Palantir and Google engineers and an experienced lawyer from a top global law firm. Our highly talented team is designed to focus on building and delivering the best product in the industry, with the engineering, product and customer expertise to fulfill this promise. We operate in major cities in North America and Europe. Our global culture means we hire only the best from around the world and value people who are respectful of their colleagues, who support each other to achieve our shared goals and who pride themselves on delivering high-quality work.

While an early stage company, we are backed by Y-Combinator, Index Ventures, and leading VC funds and are generating revenue from some of the biggest names in the industry, members of the Vault 10, Magic Circle, Am Law 100 and other rankings of law firms. Our company is growing extremely fast, with customers across multiple countries and more to come.

You will help our team grow with this rising demand and have a real impact on the most important law firms in the world.

About the Role

As an Enterprise Account Executive at DraftWise, you will own a portfolio of strategic, large law firm accounts and net-new enterprise logos. You’ll manage complex, multi-stakeholder sales cycles from initial engagement through close and expansion, working closely with DraftWise’s Head of Sales and leadership team.

You’ll build and execute account strategies for some of the largest firms in the world—partnering with senior stakeholders (partners, practice group leaders, CIOs, Knowledge Management, Innovation, and IT) to drive adoption, expansion, and multi-year partnerships.

Key Responsibilities

1. New Business & Expansion

• Own the full sales cycle for large / global law firms: prospecting, discovery, solution mapping, demos, pilots, commercial negotiation, and close.
• Develop and execute strategic account plans for named enterprise accounts, including multi-year roadmap, whitespace targeting, and expansion motions across practices, offices, and regions.
• Drive expansion of existing customers from initial land (high 5-figure deals) to mid-high 6-figure, multi-year agreements.

2. Strategic Relationship Management

• Build trusted advisor relationships with partners, practice group leaders, C-suite, KM, Innovation, and IT stakeholders.
• Orchestrate internal and external stakeholders through long, complex buying cycles - legal, procurement, security, and finance.
• Lead executive-level conversations that tie DraftWise to firm-wide initiatives such as profitability, risk mitigation, and innovation.

3. Consultative Discovery & Solutioning

• Deeply understand each firm’s workflows, tech stack, and knowledge management challenges.
• Run structured discovery to uncover business pain, value drivers, and success metrics.
• Partner with Product and Customer Success to design and position tailored solutions, pilots, and roll-out plans.

4. Deal Strategy, Negotiation & Closing

• Own pricing, proposal development, and commercial negotiations for enterprise-level contracts.
• Build clear business cases and ROI narratives that resonate with senior leadership and procurement.
• Consistently meet or exceed quarterly and annual new ARR and expansion targets.

5. Cross-Functional Collaboration

• Partner closely with Marketing on campaigns, events, and ABM programs targeting strategic firms.
• Collaborate with Product and Engineering to relay customer feedback and influence roadmap priorities.
• Work with Customer Success to ensure smooth handoffs, successful implementations, and expansion opportunities.

6. Market Intelligence & Reporting

• Stay on top of legal tech trends, competitive landscape, and emerging needs of top-tier firms.
• Maintain accurate and up-to-date pipeline, forecasting, and activity data in our CRM and sales tools.
• Share structured insights from the field to help shape GTM strategy, pricing, and positioning.

Qualifications

• Experience: 7+ years in B2B SaaS sales, with at least part of that in enterprise or mid-market/enterprise hybrid roles. Experience selling into law firms or JD is a strong plus.
• Track Record: Proven success meeting or exceeding quota, closing complex deals (high 5-figure to mid 6-figure ACVs), and expanding within existing accounts.
• Enterprise Selling Skills: Demonstrated ability to navigate multi-stakeholder, multi-threaded sales cycles involving legal, procurement, IT, and business leadership.
• Industry Knowledge: Understanding of the legal industry, professional services, or knowledge-intensive environments and the unique challenges law firms face.
• Communication: Excellent verbal and written communication skills with the ability to articulate complex, technical concepts in a clear, business-oriented way.
• Relationship Building: Strong interpersonal skills and executive presence; comfortable presenting to partners, C-level executives, and large groups.
• Analytical & Consultative: Skilled at discovery, needs analysis, and building compelling value/ROI narratives tailored to each account.
• Tech-Savvy: Comfortable with modern sales and productivity tools such as Salesforce, Salesloft, Gong, LinkedIn Sales Navigator, Apollo, etc.
• Mindset: Entrepreneurial, curious, and resourceful with a strong growth mindset; thrives in a fast-paced, early-stage environment and is comfortable with ambiguity.

Benefits

• Compensation: $300k+ OTE
• Equity plan
• Competitive salary
• Private medical care
• New laptop
• Generous PTO / sick leave
• Opportunity to lead our company as we disrupt the legal world

Technology

We have plenty of challenges at all levels of the stack, from the nuts and bolts of designing a processing back-end engine, VM infrastructure and NLP all the way up to building beautiful web technology.

If you have the appetite for it, you’ll be able to drive the product direction.

Product: React, Typescript, Redux, Postgres, Java, Elasticsearch