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Draftwise · 4 weeks ago

Enterprise Account Executive

New York City, NY

Full-time

Onsite

Senior Level

$300K/yr - $300K/yr

7+ years exp

DraftWise is an innovative knowledge platform for the legal industry, focusing on improving contract writing through data management and machine learning. As an Enterprise Account Executive, you will manage a portfolio of large law firm accounts, driving adoption and expansion through strategic relationships and complex sales cycles.

Artificial Intelligence (AI)Document ManagementEnterprise SoftwareLegalLegal Tech

Responsibilities

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

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

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 that resonate with senior leadership and procurement

Consistently meet or exceed quarterly and annual new ARR and expansion targets

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

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

Qualification

B2B SaaS salesEnterprise selling skillsLegal industry knowledgeAnalytical skillsTech-savvyCommunication skillsRelationship buildingConsultative sellingGrowth mindset

Required

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

Proven success meeting or exceeding quota, closing complex deals (high 5-figure to mid 6-figure ACVs), and expanding within existing accounts

Demonstrated ability to navigate multi-stakeholder, multi-threaded sales cycles involving legal, procurement, IT, and business leadership

Understanding of the legal industry, professional services, or knowledge-intensive environments and the unique challenges law firms face

Excellent verbal and written communication skills with the ability to articulate complex, technical concepts in a clear, business-oriented way

Strong interpersonal skills and executive presence; comfortable presenting to partners, C-level executives, and large groups

Skilled at discovery, needs analysis, and building compelling value/ROI narratives tailored to each account

Comfortable with modern sales and productivity tools such as Salesforce, Salesloft, Gong, LinkedIn Sales Navigator, Apollo, etc

Entrepreneurial, curious, and resourceful with a strong growth mindset; thrives in a fast-paced, early-stage environment and is comfortable with ambiguity