Sr. Director, Software Engineering - Workflows

Docusign • Seattle, WA

31d • $254,400 - $363,700 • Hybrid

About The Position

The Senior Director of Engineering will lead the development and scaling of our core product lines, taking them from early-stage adoption to massive enterprise scale. You will be responsible for a portfolio of products, driving the technical vision for Agentic AI applications that are not just functional but delightful to use. You will bridge the gap between complex backend AI systems and intuitive, design-forward customer-facing interfaces.
This position is a people manager role reporting to the VP of Engineering.

Requirements

• 15+ years of software engineering experience, with at least 7+ years in senior leadership roles (Director level or above)
• Experience taking multiple products (1-10+) from early concept (0 to 1) through to significant scale and revenue growth (1 to 10)
• Experience building and shipping production-level AI applications
• Experience with LLMs, Agentic AI, or autonomous systems
• Experience presenting complex technical topics to senior leadership (C-Suite) and non-technical stakeholders with clarity and confidence
• Experience working directly with external customers, including hopping on calls to support sales deals or address critical technical feedback
• Experience building complex, customer-facing enterprise B2B applications with a high bar for UI/UX
• BS/MS in Computer Science or equivalent practical experience. You can still hold your own in a technical architecture review

Nice To Haves

• Experience managing and unifying geographically distributed engineering teams across multiple time zones and cultures
• Experience building enterprise workflow products that successfully target both high-velocity Commercial (SMB/Mid-Market) segments and complex Enterprise segments
• Experience scaling engineering organizations in a high-growth startup environment (Series B to IPO)
• Understand the importance of pixel-perfect implementation and have a history of successful collaboration with creative directors
• Background in building platforms that support third-party partners or developer ecosystems

Responsibilities

• Lead multiple product engineering teams through the full lifecycle—from rapid prototyping and 0 to 1 validation to 1 to 10 growth and hardening for enterprise scale
• Architect and deliver sophisticated AI-driven applications, specifically focusing on agentic AI that can autonomously execute complex workflows for users
• Present technical strategy, roadmaps, and health metrics regularly to C-level leadership and the Board
• Act as a trusted technical advisor in high-stakes customer meetings, directly engaging with clients to understand their needs and explain our technical value
• Partner deeply with Design leadership to build enterprise-grade applications that rival consumer products in usability
• Ensure technical decisions support high-fidelity, design-heavy user experiences
• Act as a key technical partner to Go-To-Market (GTM) teams
• Work directly with Sales, Customer Success, and Support to unblock deals, resolve critical escalations, and align the roadmap with market needs
• Define the technical roadmap and organizational structure
• Recruit, mentor, and retain a world-class engineering team, fostering a culture of technical excellence and customer obsession

Benefits

• Bonus: Sales personnel are eligible for variable incentive pay dependent on their achievement of pre-established sales goals. Non-Sales roles are eligible for a company bonus plan, which is calculated as a percentage of eligible wages and dependent on company performance.
• Stock: This role is eligible to receive Restricted Stock Units (RSUs).
• Paid Time Off: earned time off, as well as paid company holidays based on region
• Paid Parental Leave: take up to six months off with your child after birth, adoption or foster care placement
• Full Health Benefits Plans: options for 100% employer paid and minimum employee contribution health plans from day one of employment
• Retirement Plans: select retirement and pension programs with potential for employer contributions
• Learning and Development: options for coaching, online courses and education reimbursements
• Compassionate Care Leave: paid time off following the loss of a loved one and other life-changing events

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 5,001-10,000 employees