Head of Technical Operations (Systems Architecture & Revenue Operations)

The Company 

Leadr is a professional speaking and thought leadership accelerator helping bold thinkers turn powerful ideas into stages, businesses, and lasting influence. We believe there’s an authentic message in everyone and, if delivered well, can change rooms and change lives.

We partner with ambitious founders, executives, and industry leaders who are ready to clarify their voice, elevate their authority, and step into bigger opportunities. Our programs combine strategic positioning, message development, and performance coaching to help clients command attention with confidence and authenticity.

We are a lean, fast-moving, fully remote team that builds with intention and our clients’ best interest in mind. No bureaucracy. No unnecessary layers. Just smart, driven people who care deeply about impact and excellence. Our company believes in the power of radical transparency and extreme ownership. And growth, both personal and professional, is part of the job.

Our culture reflects that standard. We’re proud to maintain an average employee Net Promoter Score (eNPS) of 95%, a reflection of the trust, alignment, and high-performance environment we’ve built together.

The Position

The Head of Technical Operations is the architect behind Leadr's entire technology ecosystem.

This role exists to ensure every system across marketing, sales, fulfillment, finance, and operations works together as one cohesive, scalable machine. While individual departments may own pieces of the technology stack, the Head of Technical Operations creates and owns the blueprint.

At Leadr, we view technology as a growth function of our business.

The person in this seat is responsible for designing and maintaining the infrastructure that allows the company to scale efficiently without creating technical debt, operational bottlenecks, or fragmented systems. Every CRM workflow, payment integration, automation, dashboard, reporting system, and cross-functional process should ultimately fit within a unified architecture strategy.

This role serves as the technical bridge between every department in the company. Marketing wants better attribution. Sales needs cleaner automation. Fulfillment needs better visibility. Finance needs accurate reporting. Operations needs efficiency. The Head of Technical Operations translates those business needs into scalable systems that work together.

Equally important: this role is responsible for protecting the long-term health of the company's technology ecosystem. Every new tool, automation, integration, and process should strengthen the foundation rather than create additional complexity. The Head of Technical Operations is how Leadr ensures today's solutions don't become tomorrow's problems.

Dual accountability: (1) building and maintaining the systems that allow revenue and fulfillment to scale efficiently, and (2) ensuring every system across the company remains integrated, documented, reliable, and sustainable. A fast solution that creates long-term technical debt is a failure. A perfectly designed system that slows the business down is a failure. Both things matter.

Responsibilities

Systems Architecture & Integration Strategy

Master Systems Blueprint: Own and maintain the company's architecture map, defining how every platform across marketing, sales, fulfillment, finance, and operations communicates and shares data.

Technology Governance: Evaluate, approve, and manage additions to the technology stack. Ensure every tool serves a clear purpose, integrates cleanly, and aligns with long-term company goals.

Scalability Planning: Design systems capable of supporting significant company growth. Identify bottlenecks before they impact performance and proactively improve infrastructure where needed.

Integration Oversight: Architect and oversee APIs, webhooks, middleware, and automation systems. Ensure data flows remain reliable, documented, and scalable.

Revenue Systems & Business Infrastructure

CRM Architecture: Own the structural design and optimization of HubSpot, including lifecycle stages, workflows, automation, custom properties, and cross-department reporting.

Revenue Operations Systems: Maintain the infrastructure supporting lead routing, sales automation, attribution tracking, pipeline visibility, and revenue reporting.

Billing & Payment Integrations: Ensure payment processors and revenue systems remain fully integrated and auditable, with accurate transaction-level reporting.

Fulfillment Connectivity: Create seamless connections between sales, onboarding, fulfillment, and client lifecycle systems to improve visibility and operational efficiency.

Data Quality, Reporting & Process Improvement

Data Governance: Establish standards for naming conventions, field ownership, synchronization logic, and system documentation.

Reporting Infrastructure: Build and maintain dashboards, reporting systems, and executive-level visibility into company KPIs.

System Monitoring & QA: Implement audits, alerts, and quality-control processes that identify issues before they impact customers or internal teams.

Process Automation: Identify opportunities to eliminate manual work, improve efficiency, and create scalable operational workflows across the business.

Technical Leadership & Cross-Functional Partnership

Technical Team Leadership: Lead technical contributors across the organization while ensuring build quality, prioritization alignment, and architectural consistency.

Cross-Department Collaboration: Partner closely with leaders across Marketing, Sales, Client Success, Fulfillment, Finance, and Operations to translate business requirements into technical solutions.

Documentation & Enablement: Maintain system maps, SOPs, architecture diagrams, and training materials that allow the company to scale effectively.

Vendor & Tool Management: Evaluate technology partners, manage key vendor relationships, and ensure external platforms align with company standards.

Qualifications

• United States-based or U.S. time zone based

Browse our curated collection of remote jobs across all categories and industries, featuring positions from top companies worldwide.

• Proven experience leading Technical Operations, Revenue Operations, Systems Architecture, Solutions Engineering, or similar functions within a growing organization
• Strong systems-thinking mindset with the ability to connect business strategy to technical execution
• Experience managing complex cross-functional technology ecosystems and integrations
• History of designing scalable processes, automations, and infrastructure that improve operational efficiency
• Experience leading technical teams and collaborating with senior stakeholders across multiple departments

Technical knowledge: HubSpot CRM, Zapier, Make, Stripe, PayPal, Authorize.net, Airtable, Google Workspace, Asana, Slack, Loom, Zoom, APIs, Webhooks, Data Warehousing, Business Intelligence & Dashboarding Tools, Leadpages, Infusionsoft, Reporting Infrastructure, Automation Platforms, and Systems Documentation.

Compensation + Benefits 

• Full-time, 1099 position
• Work Remotely: We're a 100% remote company with team members across North America. Save thousands of hours (and dollars) on commuting.
• Company Training & Education Fund!
• Annual All Expenses Paid Company Offsite: Our last few offsite locations include Costa Rica, Scottsdale, Orlando, and Nashville.

Salary OTE: $120k - $180kUSD depending on experience and specific expertise

Company Core Values:

• Radical Transparency 
• Extreme Ownership 
• Be a Force of Nature 
• Objective Always
• Fail Forward

Does this sound like a fit? 🎧 We'd love to hear from you!

As a fully remote organization, our hiring process may include additional application questions, a video introduction, and/or a short assignment at different stages of the process. These steps help us find the right fit for both you and our team while giving candidates multiple ways to showcase their strengths.

We appreciate your time and patience throughout the process. We're moving quickly and look forward to connecting with you soon!