Milestone - Senior Director - Engineering

Role Summary

- We're seeking a Senior Director of Engineering to partner closely with our VP of Engineering in scaling our product engineering organization. This is a role that requires strong technical depth and exceptional people and customer management skills

- You will play a pivotal role in driving product delivery, technical strategy, organizational health, and AI initiatives, working with the VP of Engineering in strategic innovation and long-term platform evolution.

- We are seeking a Senior Director with a proven track record of technical leadership and cross-functional execution to lead and scale our software product engineering teams. This role demands a strategic thinker and hands-on leader with 18+ years of industry experience, including 5+ years in leadership roles. The ideal candidate combines deep technical expertise (especially in modern software architectures, AI/ML technologies, and cloud platforms) with an ability to inspire, align, and deliver across multiple teams and stakeholders.

Key Leadership :

- Champion engineering excellence and adopt best practices in software development and system design.

- Ensure high-quality, reliable, and secure software development across teams.

- Guide modernization efforts, technical debt reduction, and platform stability.

- Drive the adoption of AI/ML capabilities across products and platforms, in collaboration with CSM. COE, web programmers, and product teams.

- Work with and guide the team in adopting AI across the organization as well as in products

People & Organizational Leadership:

- Lead, mentor, and develop engineering managers and senior individual contributors.

- Scale and structure teams to match product growth and roadmap needs.

- Foster a high-performance, inclusive, and accountable engineering culture.

- Champion career development, succession planning, and leadership grooming.

Cross-Functional Partnership:

- Act as the primary liaison between engineering and key functions like Product, Sales, digital experience, and customer success.

- Communicate engineering priorities, risks, and trade-offs clearly to business stakeholders.

- Represent engineering in leadership and strategic planning forums.

Execution Ownership:

- Understand industry and customer requirements and translate business and product goals into engineering roadmaps and team plans.

- Own delivery timelines, resourcing, and team coordination across multiple workstreams.

- Drive improvements in agile practices, metrics, and reporting across engineering functions.

Strategic Partnership:

- Partner with the VP of Engineering to evolve tech vision, drive org-wide alignment, and make critical decisions.

- Help the VP in key engineering decisions when needed.

Operational Excellence:

- Establish and track KPIs and OKRs for engineering performance, delivery, and quality.

- Own and optimize SDLC processes to improve efficiency, scalability, and reliability.

- Ensure systems are secure, scalable, and maintainable.

- Help teams to think out of the box to use AI to drive operational excellence.

Preferred Qualifications and Experience:

- Master's or Bachelor's degree in computer science, engineering, or a related field.

- Experience working in startup-to-scaleup environments.

- Background in data-intensive or AI-first products.

- Experience leading teams in a hyper growth company

- Excellent communication

What You Bring:

- 18+ years of experience in software engineering, with at least 5+ years in multi-team engineering leadership roles.

- Demonstrated experience leading cross-functional teams (Dev, QA, IT, R&D) in a SaaS or platform product environment.

- Strong technical foundation (e.g., cloud, microservices, distributed systems, platform architecture).

- Proven ability to build, lead, and scale high-performing teams.

- Strong communication and stakeholder management skills-able to align execs, product, and teams.

- Experience with agile scaling, org design, performance management, and change leadership.

- A balanced leadership style: decisive but collaborative, strategic but grounded.

- Diverse experience of working in small startups to enterprise-grade organizations.

- Having worked in AI in the last couple of years.

Why This Role Matters

- This role will be pivotal in scaling both the technology and the engineering organization. You will act as a force multiplier to the VP of Engineering, leading delivery and people development while contributing meaningfully to architectural and strategic decisions.

- You will be part of the engineering leadership team responsible for shaping our platform, culture, and execution over the next stage of growth.