Senior Enterprise Solutions Engineer

Founded in 2020, Draftwise is a contract drafting, review, and negotiation AI powered by your legal knowledge. Draftwise executes complex drafting, review, and search workflows directly within Microsoft Word, drawing from your organization's best guidance, precedent, and language.

Draftwise serves top law firms and legal departments globally, including over half the Vault 10, dozens of Am Law 100 firms, and Fortune 500 organizations. The company is headquartered in New York and has offices in London.

Draftwise is building AI that makes contract work faster and more precise for the world's leading law firms. Our platform unlocks institutional knowledge from decades of legal work, helping lawyers draft and negotiate with greater efficiency and accuracy.

You'll work alongside experienced engineers from companies like Palantir and Google, plus legal professionals from top global firms, building technology that elite lawyers use daily.

Proven Product-Market Fit
Our core technology serves the legal industry's most demanding clients. You'll build solutions that lawyers at Vault 10, Magic Circle, and AmLaw 100 firms rely on for their most important work.

Strong Foundation
Y Combinator alumni with $20M Series A funding from Index Ventures and Bek Ventures. Work with the latest generative AI and machine learning technology while having the resources to execute ambitious projects.

Meaningful Impact
Your work directly improves how legal professionals serve their clients. Build features that users actively love and depend on, with immediate feedback on real-world impact.

Global Offices & Remote Culture
Offices in New York, London, and San Francisco with the possibility of remote work. Work with a global team while maintaining the flexibility that works best for you.

• Strong communication skills in an open environment.

• The ability to work independently and make informed decisions with minimal supervision.

• Interest in working in a dynamic environment with dynamic objectives.

• A commitment to autonomy, ownership, and delivering high-quality solutions.

• Openness to giving and receiving constructive feedback.

We are seeking an experienced Senior Enterprise Solutions Architect to take a leadership role in shaping Draftwise’s technical strategy and serving as a subject matter expert (SME) in our deployment infrastructure, information security stance, and third-party integrations. This role will involve driving pre-sales engagement, leading enterprise rollout strategies, and ensuring ongoing customer success, with a strong focus on solving complex technical challenges and delivering scalable, impactful solutions that align with our customers’ strategic goals.

You will regularly interact with C-level executives, partners, and directors, requiring exceptional communication and presentation skills to effectively engage senior stakeholders.

• Technical Pre-Sales Leadership:

  • Guide customer leadership in understanding the differences between on-premise and cloud deployment options, effectively communicating the benefits of cloud adoption to support their long-term success.

  • Lead infrastructure discussions with sponsors during pre-sales and pre-conversion phases.

  • Oversee technical proof of concepts (PoCs) for prospective customers and address infrastructure-related inquiries.
    

  • Articulate security considerations, deployment trade-offs, and the operational impact of different architectures, including when using Large Language Models (LLMs).

• Enterprise Rollout Strategy:

  • Spearhead infrastructure planning and discussions to transition pilot programs into full-scale enterprise rollouts.

  • Take ownership of Document Management System (DMS) integration conversations, providing clarity and direction for successful implementation.

  • Engage senior stakeholders to articulate the value and technical architecture of rollout strategies.

• Migration Technical Leadership:

  • Oversee customer migrations from Draftwise On-Prem to Cloud, ensuring seamless transitions and alignment with enterprise goals.

  • Strategically lead and advise on migrations of customer third-party systems, such as iManage, from on-premise to cloud environments, ensuring minimal disruption and optimal outcomes.

• Strategic Upsell Enablement:

  • Drive the strategy, design, and scope of third-party integration opportunities, including assessing customer needs, identifying appropriate solutions, and collaborating with engineering teams to implement integrations (e.g. Document Management Systems (DMS), Customer Relationship Management (CRM) platforms, and other enterprise tools.

  • Collaborate on custom development projects, providing technical expertise during the sales and design phases.

• Information Security (InfoSec):

  • Address technical and security concerns or questions with client CSO/Director of Infosec.

• Stretch Goals:

  • Design and build cloud infrastructure stacks tailored to specific enterprise needs.

  • Develop innovative cloud solutions to address unique customer requests and challenges.
    

• Strong problem-solving skills with a customer-centric mindset and the ability to think quickly on your feet.

• Exceptional verbal, written, and presentation communication skills, with a proven ability to engage C-level executives, partners, and directors effectively.

• Technical experience in software engineering and system design (open-source contributions are a plus).

• Proven experience in customer-facing roles, with a strong focus on technical pre-sales and rollout support.

• A solid understanding of Infrastructure/DevSecOps principles and practices.

• Expertise in cloud infrastructure, with knowledge of on-premise systems and migration processes.

• A keen interest in and understanding of enterprise information security.

• High energy, a strong work ethic, and a proactive approach to solving challenges.
  

• Headquartered in NYC with offices in New York, and London, but Remote-first work style; Work anywhere in the US or Canada.

• Meaningful equity plan, giving you a stake in our growth.

• Competitive salary to reward your expertise.

• Private medical care to support your well-being.

• A new laptop and a work-from-home stipend for necessary accessories.

• Unlimited PTO and sick leave to prioritize work-life balance.

• The opportunity to shape our company and disrupt the legal world.