Senior Director, Software Engineering

Upland Software; Canada; Remote; CAD 90,000 - 150,000; Full time

Job summary

An established industry player is seeking a strategic Director of Software Engineering to lead diverse product engineering teams across multiple SaaS platforms. This high-impact role demands a seasoned leader with a strong technical foundation and a passion for delivering exceptional customer experiences. You will champion engineering excellence, promote innovation, and navigate complexities in a fast-paced environment. If you thrive on mentoring talent and aligning technical execution with business objectives, this opportunity is tailor-made for you. Join a forward-thinking company that values creativity and collaboration in its pursuit of digital transformation.

Qualifications

• 10+ years of engineering experience, including 5+ years in senior leadership.
• Proven success managing multiple product/platform teams in fast-moving environments.

Responsibilities

• Lead cross-functional teams across multiple tech stacks and domains.
• Build reliable and scalable products, focusing on customer experience.

Skills

Cloud-native systems

Software architecture

Secure development

Modern software development practices

Budget/resource management

Excellent communication

Collaboration skills

Education

Bachelor's degree in Computer Science or related field

Job description

At Upland Software, you’ll find smart, creative teams who love working together to deliver value for our customers, and a global culture of growth and possibility. Our operating model has always supported remote work—and as we keep growing and evolving our workplace, that won’t change. We’re passionate. We’re proactive. We take pride in our work, and we love a good challenge. Sound like you?

Role Overview:

We’re looking for a seasoned and strategic Director of Software Engineering to lead multiple product engineering teams across five unique SaaS platforms. This is a high-impact leadership role for someone who is deeply technical, thrives in a fast-paced environment, and is passionate about building high-quality software that puts customer experience at the center.

What You’ll Be Doing:

• Lead Engineering Across Multiple Platforms: Manage and support cross-functional teams working across a variety of tech stacks and domains. You’ll provide clear technical direction and ensure engineering best practices are consistently applied.
• Champion Customer Experience: Build products that are reliable, scalable, and intuitive, always keeping customer needs and feedback at the forefront.
• Promote Engineering Excellence: Foster a culture of accountability, quality, and continuous learning. Mentor senior engineers and managers, and drive performance through clear expectations and strong support.
• Be a Strategic Partner: Represent R&D in cross-functional conversations with Product Management, Sales, and Customer Success. Align technical execution with business objectives and customer outcomes.
• Drive Delivery and Innovation: Ensure products are delivered on time, with high quality. Encourage innovation, and find creative ways to invest in both people and product—even in lean cycles.
• Navigate Complexity: With five platforms and varied tech stacks, context-switching is constant. You’ll need to prioritize effectively, move quickly, and guide your teams with clarity.

What You Bring:

• 10+ years of engineering experience, including 5+ years in a senior leadership role within SaaS organizations.
• Proven success managing multiple product/platform teams in a complex, fast-moving environment.
• Strong technical foundation—cloud-native systems, architecture, secure development and modern software development practices.
• Experience working with full R&D organizations: software development, architecture, QA, and automation.
• Ability to lead through influence, resolve team dynamics, and manage performance effectively.
• Strong business acumen and budget/resource management experience.
• Excellent communication and collaboration skills.

Upland Software (Nasdaq: UPLD) is a leader in cloud-based tools for digital transformation. To learn more, visit www.uplandsoftware.com.

Upland Software is an Equal Employment Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status or other legally protected status.