Director of Engineering

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!

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

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

• 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.

• 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/Type Script front-end ecosystems.
• Exceptional communicator who operates at IC level and C-suite level equally well — with strong product sense and business acumen.

• 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.

• 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.

• 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 Tickets At Work .
• 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 Door Dash Dash Pass subscription.
• Growth Opportunities: College Assistance Reimbursement, access to EAP & Work/Life Programs, and a Linked In 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…