Head Of Engineering (With CTO Path)

Remote | Full Ownership | Clear Path to CTO

You will play a key role in helping grow the company to its next level and shape its future — through hands-on technical execution. As a Head of Engineering, you’ll lead a team of 2x passionate engineers, make meaningful product changes to grow it, solve complex challenges successfully, and deliver products that make a real impact. 

This is your opportunity to combine technical expertise with inspirational leadership & shaping our product & technical landscape, driving both the growth of your team and the success of our business. You will report to the CEO directly.

About us:

RapidSeedbox is a remote SaaS company with a mission to provide online anonymity to people worldwide.

We've been operating since 2008, serving thousands of active clients. With a clear vision for the future, our remote, passionate, and diverse team is continuously expanding, and we are on the lookout for talented individuals to join us on our exciting journey.

Watch the introduction video from our CEO & founder: https://www.youtube.com/watch?v=Rn5O4Xy1B7g

Our core values are:

• Excellence in everything we do (“I go above and beyond”)
• Ownership and responsibility (“I own my area of responsibility”)
• Continuously push the limits (“I don’t accept no as an answer. No is just an option”)
• Openness & cooperation (“Everyone matters”)

About the Role (Mission of the role):

As a Head of Engineering you will be leading our engineering team as we decouple our legacy customer area (WHMCS / PHP) into a modern web app.

This is a hands-on technical leadership role: You’ll write code most days, guide architecture and execution, and be the single engineering counterpart to the PM/CEO to translate product requirements into a clear, deliverable plan.

Hands-on vs leadership

Expect roughly 50% hands-on engineering (coding, architecture, code reviews) and 50% leadership (planning, mentorship, delivery accountability) — typical for a small team environment.

Reporting

You’ll work closely with the CEO/PM (and collaborate with the rest of the engineering team).

Your First Mission: Diagnosis (First 30 Days)

In your first 30 days, you will be in diagnosis mode. You’ll perform a deep technical + product diagnosis of our end-to-end — Tech-stack evaluation, WHMCS dependencies, billing flows, and internal tooling & customer needs.

You must be able to:

• Explain root causes vs surface symptoms clearly.
• Recommend exactly how to tackle our tech-stack limitations in the most agile & lean way possible.
• Create a 90-day execution plan that aligns technical realities with business goals

Key Responsibilities

Technical leadership (You set the standard)

• Own technical direction for the client-area/tech-stack decoupling (architecture, interfaces, incremental migration plan)
• Establish engineering best practices: code quality, reviews, testing strategy, definition of done
• Make pragmatic tradeoffs that maximize learning + delivery speed without creating future traps
• Implement AI in the tech team throughout the full development cycle to speed up development time

Delivery & Planning (You make execution predictable)

• Translate product goals into an execution plan: milestones, sequencing, risks, and dependencies
• Break down initiatives into tasks the team can execute independently
• Track progress with lightweight, real KPIs (delivery, quality, reliability), and communicate status clearly

Team Leadership (You level up the team)

• Mentor developers through feedback and coaching
• Run effective 1:1s and create clarity on expectations and growth
• Raise the bar for structured thinking and ownership across the team
• Serve as a technical leader, combining hands-on development with strategic oversight.

Hands-on engineering (You ship)

• Implement critical parts of the new client area + middleware layer
• Review PRs, improve legacy code safely, and guide refactors
• Help the team move faster through better tooling and patterns (including AI-assisted workflows while maintaining quality)

Helping Product Outcomes

• Be involved in defining the product roadmap & team expectations & help us take the right decisions to build what the customer needs.
• Be involved with ICP interviews, customer discovery, translate insights into product & tech priorities, and validate value delivered.

You’ll be a great fit if you have the following hard skills:

• Deep Technical Skills: You possess very deep technical skills which helps you bridge the gap between developers & product.
• AI + Coding: Ability to leverage AI tools for fast iteration while maintaining high quality.
• System Thinking: You understand how complex technical systems fit together — allowing you to anticipate dependencies, identify bottlenecks, and make product decisions that align with architectural realities
• Business Understanding: You understand the business side of things and the world of the customer when being involved in any tech/product decisions & You translate tech language to CEO language well.
• Excellent Communication: You communicate clearly, ask smart questions early, and surface risks before they become outages
• (Bonus) Product Excellence: You can relate and understand customer needs, uncover root problems, and help provide a voice to validate solutions before building.

You’ll be a great fit if you have the following personality traits:

• Start-up Mentality: You love wearing multiple hats, happy to own both the technical decisions and the product direction, while working in small teams, and and energized by ambiguity
• Hands-on approach: You are ready to roll up your sleeves & delve deep into intricate details of the technology & product in a fast-paced/agile work environment.
• Customer First Mentality: You understand and care about customer pains, use cases, and workflows. You understand that products & features are built from the customer's point of view rather than your own.
• Results Oriented: You take full responsibility for outcomes — not tasks. You naturally step into gaps, solve problems proactively, and operate like a founder inside the product. You are comfortable working in fast, lean, high-ownership environments.
• High Technical Passion: You’re naturally passionate about technology. You love learning how systems work — and actively seek technical depth. You ask smart questions to find solutions, dive into logs, code and thrive at the intersection of engineering and user needs
• Product-minded: You are commercially aware & product aware. You understand that engineering need to deliver business outcomes at the end of the day.

You’ll be a great fit if you have the following career background:

• 7+ years of hands-on software engineering experience, preferably in fast-paced startup environments.
• 3+ yrs of team leadership experience of an engineering team, as a CTO/VP/Head of engineering type roles.
• 2+ years of experience in a broader business or product involvement — not just backlog & technical delivery. Were involved in product decisions, and can translate engineering language to product language & business outcomes based on customer needs.
• Fluent in English, both written and verbal.

What’s in it for you:

• 100% Remote Work: Enjoy the flexibility of working 100% remotely from the comfort of your home or any location worldwide.
• Professional Growth: As we are a small company, you'll have the chance to engage with various aspects of the business, fostering your professional development.
• Mentorship & time with the CEO: You’ll get the chance to work closely 1 on 1 with the CEO & Founder of the company & receive direct coaching & help from a proven leader & entrepreneur.
• Shape the next phase of RapidSeedbox: You’ll be joining at a pivotal stage, where your ideas can genuinely influence our product. There is a real opportunity to shape the product strategy and contribute to the next phase of the company through technical execution. Your voice will be heard. You’ll work closely with leadership and have the space to experiment, learn, and make a visible impact.
• Friendly Environment: Work in a supportive and friendly environment where collaboration, respect, and positivity are part of every day.
• Emergency Fund: We offer an interest-free emergency fund with comfortable payouts to help you in times of need.
• Paid Time Off: Take as many paid time-offs as you need to ensure you are well-rested and ready to tackle new challenges.

Interview flow:

We take hiring seriously. We want to make sure we are a great match and that you can be successful & happy here.

• Initial Screening Call: Everything starts with a 30-minute call & Filling a form application (Up to 30 minutes). We appreciate candidates who take the time to thoughtfully answer our questions and share relevant information. This helps us understand your background and motivations.
• Competency Interview (1 hour): In this phase, we focus on the specific skills and traits needed for the role
• 2x Technical Interviews with CTO (45-60 minutes): In this phase, we focus on your technical skills which are needed for the role. We will have 1x technical interview and 1x AI-coding interview.
• Work History (1 hour): In this phase, we focus on your specific career path and work history.
• Test task + Personality tests: In this phase, we do a test task & personality tests.
• Reference Check: Before extending an offer, we request references from past colleagues—ideally including peers, managers, and subordinates. We’ll ask you to facilitate these conversations so we can get a well-rounded view of your working style.

If this opportunity resonates with you, we are excited to meet you and welcome you to the RapidSeedbox team!