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.

The Role

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

How We Work

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.

What You’ll Be Building

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

Who This Role Is For

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

What This Is Not

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

The Opportunity

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.

Compensation

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

Altitude jobs

Hands-On CTO