Enterprise Account Executive

Enterprise Account Executive

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