Enterprise Account Executive

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

A meeting lands on your calendar

If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.