sideby is a free peer learning community where educators have quick, guided conversations about using AI in their classrooms and schools. It’s for teachers and leaders, and it serves as a transformational approach to professional development.

How does the peer-led learning work?

We strategically match you one to one with another educator in your cohort for 15-minute conversations guided by helpful prompts focused on real use in schools.

Do I need to prepare anything?

No prep needed! Just bring your questions and experience; sideby provides the prompts to support your professional learning.

Let’s work together

Check out our Head of Engineering job description and find the application below.

Head of Engineering

Posting: October 28, 2025

Hiring goal: By mid-December 2025 with a start date of Jan 6, 2026

Applications will be reviewed as they are submitted — Apply here.

Job Description

The Head of Engineering is a builder at heart — combining engineering rigor with startup curiosity to shape the foundation of sideby’s technical ecosystem. Equal parts craftsperson, systems thinker, and product-minded collaborator, this role is about more than writing code — it’s about co-creating the norms, tools, and infrastructure that power everything we build.

As an early team member and core contributor, the Head of Engineering helps define how sideby engineers — from branching strategy to testing culture to the flow of a PR review. You care about quality, speed, and joy in the build process, AND you’re excited to craft elegant solutions that unlock educator impact at scale.

Working closely with the CTO and CEO, the Head of Engineering builds and ships full-stack features while participating in early-stage architectural decisions, platform evolution, and culture development. You thrive in ambiguity, learn in the open, and see startup life not just as a job — but as a generative act of building something that matters.

Responsibilities

Technical Execution and Architecture

Build and maintain key features across the stack — from frontend flows to backend logic and infrastructure.
Collaborate with the CTO to define and evolve our architecture to support scale, performance, and developer happiness.
Make thoughtful, pragmatic technical choices that serve both near-term needs and long-term sustainability.

Engineering Norms and Culture

Establish early development practices around testing, documentation, code review, deployment, and technical debt.
Champion a team culture of curiosity, feedback, shared learning, and continuous improvement.
Model sideby’s values in how we build software — balancing rigor, transparency, and adaptability.

Product Collaboration and User Impact

Translate product specs and user needs into intuitive, performant engineering solutions.
Work closely with the team and community to ensure features are grounded in real-world educator workflows and aspirations.
Infuse builds with attention to accessibility, UX, and design principles.

Startup Systems and Infrastructure

Co-create the workflows, environments, and dev tooling that make it easier to build at sideby.
Set up and maintain CI/CD pipelines, observability systems, and monitoring to ensure stability and speed.
Identify and fix bugs quickly while maintaining a culture of learning and shared responsibility.

Cross-Functional Collaboration

Participate in cross-functional sprints and design sessions.
Contribute to team planning and OKRs, ensuring engineering is aligned to broader goals and outcomes.
Serve as a technical voice and thought partner across the team by helping others understand tradeoffs, opportunities, and constraints.

External Engagement and Engineering Voice

Partner with the CEO and CTO to represent our technical approach with potential partners, funders, and team.
Help shape how we talk about our engineering choices, from stack decisions to team culture.
Support in hiring, onboarding, and mentoring as we grow the engineering team.
Partner appropriately and effectively with external dev teams or dev support as needed in scoping, hand offs, and collaboration.

Community and Curiosity-Driven Engagement

Engage in team conversations with empathy, humor, and clarity by modeling our norms and shared values.
Celebrate small wins, surface blockers, and invite feedback with consistency and care.
Stay curious by keeping up with relevant tech, frameworks, and ideas that might strengthen our work.

Community and Tech Support

Actively engage in educator support channels as needed, including shared inboxes, in-app feedback, and async community spaces to help ensure users feel heard, supported, and celebrated.
Troubleshoot bugs and technical issues with clarity and empathy — prioritizing educator experience while surfacing patterns to into actionable product insights, fixes, and technical improvements.
Model curiosity-driven engagement with educators — listening deeply, responding helpfully, and reinforcing sideby’s stance that learning is a shared, evolving process.
Support educators in getting value from the product — from helping someone find a feature to celebrating a small win they shared with the team.
Ensure technical support is not transactional and acts as a space where educators feel connected, not confused; empowered, not dismissed.

Leadership and Culture

Model sideby’s values and norms. Seek and expect collaboration.
Foster a culture of clean code, kind reviews, and joyful iteration by making engineering both rigorous and human.
Help shape the norms of a startup engineering team from scratch by balancing velocity with care, and craft with curiosity.
Coach, mentor, and support teammates as we grow by offering feedback that builds trust, sharpens thinking, and reflects a shared commitment to excellence.
Hold space for uncertainty, conflict, and learning to help build a culture where growth is expected, feedback is kind, and outcomes are shared.

Subject to Change

All of this is subject to change. All terms, including job responsibilities, compensation, and benefits, are subject to change depending on company needs and legal requirements.

Inclusive Hiring

sideby is committed to creating an inclusive and equitable workplace. We do not discriminate on the basis of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, disability, age, veteran status, or any other protected characteristic. All employment decisions are made based on qualifications, merit, and business needs.

Overview

Status

At-Will, Full Time Employment reporting to the CEO

Compensation and Equity

Base Salary Range: $106,000 - $120,000 (full-time)
Plus Equity: Incentive Stock Options (ISOs)

Granted under sideby's 2025 Stock Plan
Standard 4-year vesting with a 1-year cliff, followed by monthly vesting

This role includes meaningful equity as part of your total compensation. You’ll have the opportunity to own a real stake in what you’re helping to build, from early-stage experiments to long-term impact.

Remote

This is a fully remote position, allowing you to work from anywhere in the United States. While the role is primarily remote, some travel (~5%) may be required to support clients, engage in company-wide gatherings, or provide in-person services as needed. Travel expectations will be determined based on client and company needs and are subject to change.

Retirement

sideby offers retirement benefits for employees. Currently, this is a 401k from Human Interest which becomes available after 3 months of employment. There is an employer 100% match up to 1% of compensation, 50% match up to 6% of compensation. Vests on a two year cliff.

Office Set Up

Up to $1000 for the initial set up of your sideby home office to support a safe, ergonomic home workspace.

Biannual Bonus Eligibility

Eligibility to receive bonuses twice per year, typically in June and December, based on individual performance, team goals, and company profitability.

Work Calendar & PTO Policies: - Flexible schedule, 36 hour work week, unlimited PTO, generous holidays with some shared on call potential for tech support

Apply here.