Hands-On CTO

Waystone Software is building Altitude. The operating system for modern financial advisory firms. We combine CRM, marketing automation, practice management, and AI into one integrated platform designed to help advisors run better businesses for decades to come.

We are looking for a hands-on CTO who has built before, learned the hard lessons, and is ready to build again.

This is a leadership role for someone who wants real ownership, real impact, and real upside.

As CTO, you will own the technical direction and execution of Altitude. You will scale an already-working platform, lead a growing engineering team, and help shape how AI, automation, and data come together in a regulated environment.

This is not a “manage from a distance” role. You will be close to the code, the product, and the people.

You will:

• Own the technical vision, architecture, and execution
• Write production code regularly
• Lead and mentor engineers with high standards
• Scale the platform for performance, reliability, and security
• Design practical, scalable AI systems
• Make smart build vs buy decisions
• Partner closely with product, marketing, and leadership
• Engage in direct, thoughtful problem-solving with the founder and leadership team, from whiteboard to production
• Help turn a strong product into a category-defining platform
  

Altitude is founder-led and product-driven. The founder sets the vision and direction, and works closely with engineering to turn big ideas into real, usable systems.

We value strong judgment, good product taste, and the ability to think a few steps ahead. We talk things through, sketch ideas, challenge assumptions, and then get to work.

We take building seriously, work hard, and move fast. We also enjoy working together, keep things human, and believe that great teams do their best work when there’s trust, energy, and a sense of fun along the way.

• A modern CRM, marketing automation platform, and AI assistant built specifically for advisory firms
• Workflow systems that drive consistency, efficiency, and growth
• AI-powered assistants and agents that deliver real business outcomes
• Secure systems handling sensitive PII
• Infrastructure designed to scale with speed, discipline, and durability

You are likely a great fit if you are:

• A startup veteran who has shipped and scaled real products
• Comfortable leading and building
• Experienced with modern web platforms and cloud infrastructure
• Strong in AI systems, automation, and data-driven architecture
• Product-minded and business-aware
• Hungry to build something meaningful and long-lasting
• Excited by in-person collaboration and fast decision-making
• Comfortable working with a founder who is deeply involved in product and strategy

You’ll do well here if you:

• Enjoy building systems that encode best practices, not just features
• Care about long-term leverage and durability over short-term hacks
• Prefer clarity and momentum over process for its own sake

Typical background:

• 8 years of hands-on engineering experience
• Prior CTO, VP Engineering, or senior technical leadership at a startup
• Deep experience with modern stacks (React, Next.js, APIs, AWS, Prisma)
• Experience scaling systems and teams beyond early traction

Nice to have:

• CRM, marketing automation, or workflow platform experience
• Regulated industry experience (fintech, wealth management, healthcare)
• Prior founder or early-employee experience
  

• Not remote or hybrid
• Not a people-only management role
• Not an advisory or fractional CTO position
• Not a big-company, slow-moving environment
  

Altitude is not trying to be another CRM. We are building a platform that captures decades of hard-earned best practices and makes them actionable through software and AI.

If you want to build something new, cutting edge, that compounds in value, stands the test of time, and helps real businesses run better, this is that opportunity.

• Competitive salary
• Meaningful equity ownership
• Long-term growth opportunity
• Health, Dental, Vision, 401k Matching
• Healthy, fun environment to grow in
• Snacks