Director of Engineering (US Remote)

Who we are: Alignable is the largest online network of small business owners, with over 10 million members across North America. Our mission is to empower small businesses by helping them build trusted relationships and grow through referrals, connections, and community. We don't just connect business owners—we unlock the hidden potential in their existing networks by revealing second- and third-degree relationships that drive real business growth. Think of it like this: when a software engineer realizes their college roommate's older brother is the hiring manager at the startup they want to join, or when a founder discovers their neighbor's former colleague is exactly the technical co-founder they need—that's our platform at work, but for small businesses. We built the technology that makes those invisible connections visible. Here's the technical challenge we've solved: we're processing relationship data across 30,000+ communities, building recommendation engines that surface the most valuable connections, and creating trust-based networking algorithms that actually work. This isn't just social networking—it's relationship intelligence at scale. With 20,000+ new freemium members joining each week, we're entering a new phase of scale where product-led growth (PLG) is core to our transformation. As a profitable Series C company, we're not burning cash hoping to find revenue—we're scaling proven technology that millions of real entrepreneurs depend on to build their businesses. Your work here directly impacts the backbone of the American economy. Small businesses employ nearly half of all American workers, and when your code helps them find customers, suppliers, or services through trusted referrals, you're making a tangible difference in millions of lives. If you want to empower the small business owner through a networking platform unlike any other, let's talk. The Opportunity: We're looking for a Director of Engineering to lead our engineering organization through its next chapter of growth. This is a critical leadership role on our executive team—you'll own the technical strategy, team development, and delivery for ~26 engineers across multiple squads. This role reports directly to our Co-Founder/President and has a clear path to VP of Engineering. You'll partner closely with Product, Design, and Data leadership to shape what we build and how we build it—while ensuring our engineering culture continues to attract and retain exceptional talent. What you will be doing: Leading the Engineering Organization You'll own the health, performance, and growth of our engineering team. This means building strong Engineering Managers, establishing clear career paths, running calibrations and performance cycles, and creating an environment where engineers do their best work. You'll directly manage 3 Engineering Managers and several senior individual contributors, with ~26 engineers in your organization overall. Setting Technical Direction You'll shape our technical strategy in partnership with senior engineers and cross-functional leaders. This includes making decisions about architecture evolution, AI/ML integration, platform scalability, and technical debt prioritization. You won't be writing code day-to-day, but you'll provide technical guidance through architecture reviews, design discussions, and mentoring senior engineers. Your technical judgment will help teams make the right trade-offs. Driving AI Integration We're integrating AI throughout our platform to bring AI-powered features to 10+ million small business owners. You'll champion AI adoption across the engineering org—ensuring teams have the skills, tools, and architectural patterns to ship AI-powered products effectively. You'll also drive AI-assisted development practices (AI coding tools, automated testing, workflow automation) to accelerate engineering velocity. Whether it's LLM-based features for customers or AI tools that help engineers ship faster, you'll guide the strategy and remove blockers. Driving Delivery and Operational Excellence You'll ensure we ship high-quality products on predictable timelines. This means optimizing how squads work together, establishing engineering metrics that matter, improving our incident response and reliability practices, and removing organizational friction that slows teams down. Partnering Cross-Functionally You'll be a key voice in product strategy, partnering with Product and Design leadership to balance business needs, user value, and technical sustainability. When the CEO wants to understand engineering capacity or a PM needs to make a build-vs-buy decision, you'll be the person in the room. Building for Scale As we grow, you'll evolve our engineering organization—hiring senior talent, establishing new squads, improving our technical interview process, and ensuring our org structure supports our product roadmap. Our tech stack:

Frontend: Typescript, React, Jest

Backend: Ruby on Rails, Elixir, Phoenix, Go

Databases: Postgres, Redis, DynamoDB, OpenSearch

Mobile apps: Kotlin and Swift

Deployment: CI/CD with Github and AWS

Analytics: Kinesis, Lambda, Python, Pandas, Snowflake

Machine Learning: Pytorch, Tensorflow, Sagemaker

LLMs: Claude, GPT, plus other AI tools

What success looks like:

In your first 90 days: You'll have built trust with your direct reports and key cross-functional partners, developed a clear picture of team health and delivery challenges, and identified 2-3 high-leverage improvements to pursue.

In your first 6 months: You'll have established your leadership rhythm (1:1s, team meetings, calibrations), driven measurable improvements in engineering velocity or quality, and partnered with Product to shape the roadmap for the next half.

In your first year: Your engineering organization will be demonstrably stronger, better retention, clearer career paths, more predictable delivery, and a technical strategy that's aligned to business goals. You'll be a trusted member of the executive team with a clear path to VP.

What you will bring:

Engineering Leadership Experience: 8+ years in software engineering with at least 4 years leading engineering teams, including experience managing managers. You've built and scaled teams of 20+ engineers at growth-stage companies.

Technical Credibility: You've been a strong IC in your past and can still go deep on architecture, system design, and code quality. You don't need to be the best coder in the room, but you need to earn the respect of senior engineers through your technical judgment.

Delivery Track Record: You've shipped products that matter at companies with real scale. You know how to balance speed and quality, manage technical debt, and keep teams focused on outcomes over output.

People Development: You've grown Engineering Managers and senior ICs. You have a track record of retention and promotion. You know how to give hard feedback and have hard conversations.

AI/ML Familiarity: You've shipped AI-powered product features or led teams integrating LLMs and ML into products. You're excited about what AI can do for small businesses—and for engineering productivity.

Cross-Functional Partnership: You've worked closely with Product, Design, and business leadership. You can translate between technical and non-technical stakeholders and influence without authority.

Experience with our stack is a plus: Ruby on Rails, Elixir, React/TypeScript, AWS. But we care more about your ability to learn and lead than matching every technology.

Why Alignable?

Executive Impact: Join the leadership team at a profitable Series C company with a clear path to VP. Shape engineering strategy and culture at a pivotal moment in our growth.

Mission-Driven Work: Help 10+ million small business owners thrive. Your work directly impacts the backbone of the American economy.

Exceptional Remote Culture: Join highly collaborative cross-functional teams guided by experienced leadership from Invisalign, Constant Contact, and Vistaprint. Work from anywhere with East Coast US hours.

Inclusive Environment: Be part of a team that celebrates diversity like the small business community we serve, with core values emphasizing psychological safety, continuous learning, and bringing your authentic self to work.

What we offer:

Smart, supportive co-workers

Competitive compensation

Equity

Health, dental, and vision insurance

Unlimited vacation policy

Virtual working environment

Flexible working hours

Paid Parental leave

Professional Development Program

401(k)

Our culture in action:

🎉Enjoy the Journey: We're passionate about our mission but don't take ourselves too seriously. We celebrate customers, teammates, and key moments.

🤝 Be Stronger Together: We combine strengths, build trusted relationships, and treat everyone as partners. No egos welcome.

🌈Be Different Together: We create space for everyone to show up as their truest selves and seek diverse perspectives.

👑Act Like an Owner: We proactively act on behalf of the entire company and customers, not just ourselves. No passing the buck.

🎯Change the Game: We start with first principles, assume nothing is impossible, and go after 10x outcomes relentlessly.

📈Adapt & Evolve: We accept we won't be right every time and create an environment where people feel safe to admit failure and lean into learning.

🧠 Exercise Excellent Judgment: We turn knowledge into understanding based on equal parts data and intuition.

⚡Profound Bias for Action: Speed matters. We value calculated risk-taking while avoiding one-way doors.

❤️ Be Customer Obsessed: We work vigorously to earn and keep customer trust in everything we decide to work on and how we do it.