Full time. 100% Remote work opportunity. Compensation negotiable.

Head of Technical Operations

Build rock-solid systems, geek out on AI, and do work that actually matters - from anywhere.

Who You Are

You know that feeling when you're deep in an automation workflow at 2am, not because you have to be, but because you genuinely want to see it work perfectly?

When "data integrity" gives you a little dopamine hit?

When you find yourself explaining to friends why proper webhook architecture actually matters?

The Opportunity

Love At First Fight is an online education company that helps couples repair their relationships - work that genuinely changes lives and families.

Our founder, Bruce, is ready to step out of the technical weeds entirely and focus on being CEO.

We are looking for someone to fully own the tech stack he’s built, to:

• Keep it stable…
• Prevent the fires instead of fighting them…
• Improve it, and…
• Thoughtfully integrate AI where it creates real leverage.

What You'll Own

You’ll own the technical backbone of a company that actually helps people, and we want someone who finds joy in knowing that their work makes a difference.

You’ll own:

WordPress & Platform Infrastructure
Our site runs on WordPress with Thrive Apprentice, custom PHP, ThriveCart, WebinarJam, webhooks, and AI-related code. You'll own safe update procedures, staging environments, security, performance, and uptime. Stability first, elegance second.

Automation Infrastructure
Around 25 n8n automations handle product delivery, onboarding triggers, and refund prevention. These directly affect revenue. You'll monitor, troubleshoot, improve, build new ones as needed, and migrate legacy Pabbly automations into n8n.

ActiveCampaign
This includes: CRM Tags, message variables, event logic, split-testing, delivery timing, and personalization across sales, onboarding, and retention. You'll create list logic and tracking for email sequences written by Bruce or copywriters.

Tracking & Attribution
This includes: ClickMagick, Google Analytics, Meta, WebinarJam, and ThriveCart. Accurate UTM creation and tracking proper attribution, diagnosing issues, and implementing tracking for new funnels.

Vendor & Platform Liaison
You'll be our primary technical contact with third-party platforms like ThriveCart, ThriveThemes, ActiveCampaign and other WordPress plugin vendors to:

• gather logs
• reproduce issues
• communicate clearly with support teams
• drive issues/bugs/glitches to resolution

After your ramp-up, Bruce shouldn't need to touch vendor support.

Documentation
Documentation isn't a 'nice to have' - it's how we ensure someone else could step in if needed. You’d document:

• System architecture
• Automations
• Update procedures
• Incident resolution
• Recovery steps

You’d use AI to help document and keep our documentation organized and easily accessible.

Coding Custom Software & Internal Tools
If this is an area you enjoy, you’ll also have the opportunity to oversee and shape custom software development. This is a growth opportunity within the role, not a requirement.

This may include:

• Designing and overseeing small custom tools or internal systems
• Using AI-assisted development/vibe coding to prototype or build software
• Defining requirements and architecture for custom features
• Reviewing, improving, or extending existing custom code
• Ensuring any custom software is reliable, well-documented, and aligned with the broader platform

What Success Looks Like (Six Months In)

Bruce isn't contacted about technical issues. Problems get resolved before customers notice. Automations run reliably and quietly. Updates happen calmly, safely, and deliberately. Systems are documented clearly enough that someone else could step in. AI tools are being integrated in a stable, predictable way.

The platform feels boring - in the best possible way.

How Autonomy Develops

Initially, you'll work closely with Bruce while learning the system he’s built, and production changes will require approval. Over time, you earn full autonomy and own production end-to-end. Success means Bruce no longer needs to think about technical operations at all.

Experience We're Looking For

We don't expect you to know every platform we use — what matters more is that you can learn and master new systems. That said, here's what we're looking for:

Must-Haves

• Strong WordPress experience in production environments
• Hands-on experience with automation tools (n8n or similar)
• Comfort with APIs, webhooks, and custom integrations
• Working proficiency in HTML, CSS, and PHP - enough to troubleshoot and safely modify live systems
• Experience maintaining live, revenue-critical systems
• High integrity, accountability, and follow-through

Nice-to-Haves

• Experience with tracking, UTMs, and attribution systems
• Working knowledge of DNS, domains, hosting/server configuration
• Experience maintaining servers or VPS environments
• Familiarity with CDNs like Cloudflare
• Understanding of email deliverability (SPF, DKIM, DMARC, sender reputation)
• A working understanding of AI concepts and enthusiasm for applying AI in production
• Interest in AI-assisted development and "vibe coding"

This Role Is For You If You...

• Enjoy working independently without constant oversight
• Get excited about owning the core functionality of a business
• Take pride in reliability and responsibility
• Think proactively about failure points and edge cases
• Prefer clear procedures, documentation, and repeatable processes
• Stay calm and methodical when things go wrong
• Have strong opinions, but hold them loosely when presented with better information
• Enjoy learning unfamiliar systems and mastering them over time
• Are genuinely interested in AI and enjoy experimenting with practical applications

This Role Is Not For You If You...

• Prefer constant novelty or frequent tool changes
• Enjoy being the hero in emergencies more than preventing them
• Dislike documentation and communication
• Don't want to keep up with technological advances like AI
• Want a short-term freelance engagement
• Prefer rebuilding systems over stabilizing them

What’s In It For You?

Fully remote with flexible hours - we care about outcomes, not time tracked.

Meaningful impact. You'll be supporting a business that helps couples repair relationships and families. The work actually matters.

Intellectual respect. Your judgment will be trusted. Strong opinions are welcome when backed by experience.

Human-first culture. We care about you as a person and team member - not just a technical resource. Our team actually enjoys working with each other.

Mission-critical role. What you build, maintain, and protect directly affects revenue, customer experience, and scalability.

High trust, low-drama, low-meeting culture. Once trust is earned, you'll have real autonomy and ownership.

Application Process:

1. Record a 5 minute video introducing yourself to us. It doesn't have to be professional, as long as you're well lit. 
2. Then, complete a 15-minute personality quiz.
3. Finally, upload your CV.

Please complete all of these tasks (on the next page), or your application will not be considered. 

Love at First Fight is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. Apply now and help make a difference in the lives of couples worldwide!