Senior Director, Engineering

Avalara, Inc.; Northern (KY); Hybrid; USD 150,000 - 230,000; Full time

Benefits offered by this job

Bonuses

Private medical insurance

Paid time off

Parental leave

Job summary

Avalara, Inc. is seeking a strategic engineering leader to drive the next wave of AI-enabled platform innovation for a flagship SaaS product with multi‑million revenue and rapid growth.

You will oversee multi‑year replatforming, mentor high‑performing teams, and partner with PMs and data scientists to deliver AI-powered experiences at scale. You will shape the technical roadmap, champion modern infrastructure, and communicate clearly across executives, product, and engineering teams to unlock

Qualifications

• Proven success managing engineering organizations behind $50M+ product lines or similarly scaled SaaS platforms.
• A bachelor’s degree (or higher) in Computer Science is required.
• A solid engineering foundation—capable of understanding, building, and scaling complex systems.
• Expertise in platform modernization (replatforming, scalability, microservices, etc.) coupled with a strong understanding of AI-driven product development.
• A track record of building and mentoring high-performing teams, with a leadership style that’s both empowering and execution-focused.
• Clear, strategic communication—comfortable engaging across technical, product, and business teams.

Responsibilities

• Lead and inspire engineering teams through a multi-year transformation, including replatforming legacy components and building modern, scalable infrastructure.
• Drive innovation by weaving AI into the product’s core—working hand-in-hand with PMs and data scientists to deliver customer-facing, AI-powered experiences.
• Own the product’s technical roadmap, ensuring it aligns with business objectives, customer demands, and long-term scalability goals.
• Foster a culture of excellence, accountability, and forward-thinking engineering.
• Act as a strategic advisor to executive leadership on AI integration, technical investment, and product growth strategy.

Skills

AI product dev

Platform modernization

System scalability

Leadership

Cross-functional communication

Education

Bachelor's degree in Computer Science

Tools

Cloud platforms

AI tooling

Job description

What You'll Do

We're looking for a strategic and technically strong engineering leader to drive innovation and scale for one of Avalara's flagship SaaS products—a $50M revenue-generating line with double-digit growth and a customer base in the hundreds of thousands. This is more than just a leadership role. It’s a chance to put your fingerprint on one of the top AI-enabled platforms in the industry, steering both its near‑term transformation and long‑term innovation strategy.

#LI-Remote

What Your Responsibilities Will Be

• Lead and inspire engineering teams through a multi-year transformation, including replatforming legacy components and building modern, scalable infrastructure.
• Drive innovation by weaving AI into the product’s core—working hand-in-hand with PMs and data scientists to deliver customer-facing, AI-powered experiences.
• Own the product’s technical roadmap, ensuring it aligns with business objectives, customer demands, and long-term scalability goals.
• Foster a culture of excellence, accountability, and forward-thinking engineering.
• Act as a strategic advisor to executive leadership on AI integration, technical investment, and product growth strategy.

What You'll Need to be Successful

• Proven success managing engineering organizations behind $50M+ product lines or similarly scaled SaaS platforms.
• A bachelor’s degree (or higher) in Computer Science is required.
• A solid engineering foundation—capable of understanding, building, and scaling complex systems.
• Expertise in platform modernization (replatforming, scalability, microservices, etc.) coupled with a strong understanding of AI-driven product development.
• A track record of building and mentoring high-performing teams, with a leadership style that’s both empowering and execution-focused.
• Clear, strategic communication—comfortable engaging across technical, product, and business teams.

This Role Is For You If…

• You're an engineering leader ready to scale something meaningful, not just maintain the status quo.
• You see AI as a tool for product differentiation—not just a buzzword—and know how to apply it with intent.
• You thrive in high-impact environments where visibility is high and the opportunity to influence is even higher.

What Makes This a Bar-Raiser Role

AI Bar Raiser

At Avalara, this role is expected to be an AI Bar Raiser — a leader who elevates both the technical capability of the organization and the practical application of AI across engineering and operational workflows.

This individual is expected to apply advanced AI capabilities to materially improve how systems are designed, built, operated, and scaled, while driving measurable gains in engineering productivity, quality, automation, and business impact. The expectation is to create a culture of 10x productivity through the effective use of AI tools, modern engineering technologies, automation, and an agile execution mindset where speed is table stakes.

Bar Raiser

At Avalara, this role is expected to be a Bar Raiser who strengthens teams by improving technical judgment, accelerating organizational learning, mentoring engineers and leaders, and leaving platforms, processes, and operating models significantly better than they found them.

• This role is expected to redefine how engineering, AI, and content operations work together at scale across Avalara.
• Success requires building not only a technically strong platform, but also a durable operating model that improves execution speed, quality, scalability, and business impact.
• The leader in this role must consistently raise the bar across architecture, engineering discipline, AI adoption, operational excellence, talent density, and cross‑functional execution.
• The ideal candidate combines deep technical judgment with strong organizational leadership and has a demonstrated track record of delivering complex platform transformations with measurable outcomes.
• This is a highly visible leadership role with direct influence on Avalara’s AI strategy, content scalability, and long-term operational efficiency.

Avalara is an AI-first Company

AI is embedded in our workflows, decision-making, and products. Success here requires embracing AI as an essential capability.

• You’ll bring experience using AI and AI-related technologies, ready to thrive here.
• You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.
• You’ll grow with AI by staying curious about new trends and best practices, and by sharing what you learn so others can benefit too.

How We’ll Take Care of You

Total Rewards

In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses.

Health & Wellness

Benefits vary by location but generally include private medical, life, and disability insurance.

Inclusive culture and diversity

Avalara strongly supports diversity, equity, and inclusion, and is committed to integrating them into our business practices and our organizational culture. We also have a total of 8 employee-run resource groups, each with senior leadership and exec sponsorship.

What You Need To Know About Avalara

We’re defining the relationship between tax and tech.

We’ve already built an industry-leading cloud compliance platform, processing over 54 billion customer API calls and over 6.6 million tax returns a year. Our growth is real - we're a billion dollar business - and we’re not slowing down until we’ve achieved our mission - to be part of every transaction in the world.

We’re bright, innovative, and disruptive, like the orange we love to wear. It captures our quirky spirit and optimistic mindset. It shows off the culture we’ve designed, that empowers our people to win. We’ve been different from day one. Join us, and your career will be too.

We’re An Equal Opportunity Employer

Supporting diversity and inclusion is a cornerstone of our company — we don’t want people to fit into our culture, but to enrich it.

All qualified candidates will receive consideration for employment without regard to race, color, creed, religion, age, gender, national orientation, disability, sexual orientation, US Veteran status, or any other factor protected by law.

If you require any reasonable adjustments during the recruitment process, please let us know.