Director of Engineering

Vagaro; Pleasanton (CA); On-site; USD 260,000 - 285,000; Full time

Benefits offered by this job

Health insurance

On-site gym

DoorDash DashPass

TicketsAtWork discounts

401k with matching

PTO + holidays

Job summary

Vagaro seeks a Director of Engineering to lead and scale our software organization on a modern Azure-based stack. You will own technical vision, cross-functional delivery, and team culture, reporting to the CPTO and collaborating with the CEO.

The role is onsite in Pleasanton, CA, with a focus on AI/ML integration, platform modernization, and scalable architecture to serve thousands of customers.

Qualifications

• 10+ years in software engineering with 4+ years leading engineering teams in SaaS/Fintech.
• Proven ability to scale teams, ship product, modernize platforms, and embed AI.
• Deep expertise in Azure cloud services and REST API/microservices architecture.
• Fluency in modern JavaScript/TypeScript front-end ecosystems.
• Exceptional communicator who operates at IC and C-suite level with strong product sense.

Responsibilities

• Lead and scale the engineering organization; own technical vision and delivery.
• Define and drive the technical roadmap with the CPTO and CEO; balance velocity with reliability.
• Oversee architecture across Azure, front-end, and REST services; enforce CI/CD and best practices.
• Define AI/ML/GenAI strategy and communicate trade-offs to leadership and partners.

Skills

Team Leadership

Technical Strategy

AI/ML Strategy

Azure Cloud

REST API

JavaScript/TypeScript

C-suite Communication

Tools

Azure

CI/CD

REST API

Job description

Why Vagaro?

At Vagaro, we believe in fostering a collaborative and inclusive work environment where every team member can thrive. Our culture is built on innovation, continuous learning, and a passion for making a positive impact. We support our employees' growth and vision for themselves, offering opportunities for professional development and career advancement. Join us and be part of a team that values creativity, teamwork, and a commitment to excellence. Plus, we know how to have fun while getting the job done!

What you'll Be Doing:

We are a large-scale SaaS and Fintech company seeking a Director of Engineering to lead and scale our engineering organization. Reporting to the CPTO and working closely with the CEO, you will own technical vision, engineering execution, and team culture on a modern Azure-based stack — driving the organization across team growth, delivery, platform modernization, and AI/ML integration.

*This role is based onsite in Pleasanton, CA Monday through Friday*

Compensation

• Base Annual Salary: $260,000 - $285,000
• Annual Bonus: Up to 20%

Your Impact:

• Team Leadership
  • Manage and grow a team of 10–30 engineers; build career ladders, develop leaders, and foster a high-performance culture built on ownership and trust.
• Technical Strategy & Delivery
  • Own the technical roadmap in partnership with the CPTO and CEO — balancing product velocity, platform reliability, and technical debt.
  • Lead architectural decisions across Azure, front-end, and REST API services; champion engineering quality, CI/CD, and best practices.
  • Partner with Product and Design to drive predictable, high-quality delivery and agile execution.
• AI, Innovation & Cross-functional Influence
  • Define and execute an AI/ML and GenAI strategy — from LLM integration to scalable MLOps foundations — that differentiates the product.
  • Communicate engineering strategy and trade-offs clearly to the CPTO, CEO, and partners across Sales, Customer Success, and Security.

What you Bring:

• 10+ years in software engineering with 4+ years leading engineering teams in SaaS and/or Fintech environments.
• Proven ability to scale teams, ship product, modernize platforms, and embed AI — simultaneously, not sequentially.
• Deep expertise in Azure cloud services and REST API / microservices architecture; strong command of observability and security standards.
• Fluency in modern JavaScript/TypeScript front-end ecosystems.
• Exceptional communicator who operates at IC level and C-suite level equally well — with strong product sense and business acumen.

Nice to Have:

• Hands-on experience integrating AI/ML, LLMs, or GenAI into production applications.
• Experience in regulated industries (Fintech, healthcare) and related compliance frameworks (SOC 2, PCI-DSS).
• Hands-on React experience in a production environment.

What you Bring:

• High-visibility leadership role with direct access to the CPTO and CEO — your voice shapes company direction.
• Opportunity to build, modernize, and scale an engineering organization at enterprise scale.
• Be at the forefront of embedding AI/ML into a SaaS and Fintech product that impacts thousands of customers.
• Competitive compensation, benefits, and the energy of a collaborative on-site team in Pleasanton, CA.

Why You’ll Love Working Here:

• Attractive Compensation & Performance Bonuses: Enjoy a competitive salary paired with performance-based bonuses
• Generous PTO: 15 accrued days, plus 10 company holidays annually.
• Health & Wellness: Comprehensive healthcare, dental, and vision plans for you and your family.
• Exclusive Perks: Discounts on attractions, theme parks, shows, sports events, movies, hotels, and more through TicketsAtWork.
• Beauty Perks: $30/month reimbursement for any Vagaro service, including health, beauty, or wellness treatments.
• Food Perks: $50 monthly stipend for our onsite microkitchen and a complimentary DoorDash DashPass subscription.
• Growth Opportunities: College Assistance Reimbursement, access to EAP & Work/Life Programs, and a LinkedIn Learning account.
• Financial Security: 401k program with 4% matching and optional life/supplemental insurance.
• Stay Active: Access to our on-site gym, flavored water dispenser, and basketball court to keep you fit and energized!

Equal Opportunity Employer:

Vagaro is proud to be an Equal Employment Opportunity and affirmative action employer. We foster an inclusive environment where individuals are evaluated without discrimination based on gender, race, ethnicity, age, disability, religion, sexual orientation, gender identity, veteran status, or any other characteristics protected by law.

Privacy Policy:

Your privacy matters! At Vagaro, we are committed to protecting your personal information. Before proceeding with your application, please review our Employee and Applicant Privacy Notice here. By submitting your application, you acknowledge that you have read and understood our Privacy Notice, which outlines how we collect, use, disclose, and protect your information during the recruitment and employment process.

Vagaro is an E-Verify employer. Learn more at www.e-verify.gov

Learn More About Vagaro:

Visit us at vagaro.com/pro and vagaro.com to learn more.].