Senior Technical Lead

Calibrate Group AI·Remote·Work From Anywhere·
60,000 - $200,000
Other
HubSpot

WFA Digital Insight

As demand for AI-powered solutions grows, companies like Calibrate Group AI are seeking visionary technical leaders to drive their technical strategy. With the remote job market booming, professionals with expertise in HubSpot and AI-native workflows are in high demand, with some estimates suggesting a 25% increase in job openings for similar roles. Calibrate Group AI stands out for its innovative approach to AI implementation, and candidates should be prepared to showcase their ability to think in business outcomes, not just code. With the company's focus on effectiveness and co-builder roles, this is an exciting opportunity for those looking to make a real impact.

Job Description

About the Role

The Senior Technical Lead at Calibrate Group AI is a unique opportunity for a seasoned technical professional to own the technical vision and execution of the company's AI-powered solutions. As a co-builder role, this position requires a visionary leader who can design and build custom AI implementations for small to medium-sized businesses, integrating with existing platforms such as QuickBooks, HubSpot, and more. The successful candidate will be responsible for leading a small team and driving the technical strategy of the company, with a focus on delivering real business outcomes.

Day-to-day, the Senior Technical Lead will be responsible for designing and building custom AI implementations, integrating with existing platforms, and managing the technical hiring process as the company scales. This is a highly autonomous role, requiring a self-motivated individual who can build and maintain complex systems, think creatively, and communicate effectively with both technical and non-technical stakeholders.

What You Will Do

  • Design and build custom AI implementations for small to medium-sized businesses
  • Integrate AI solutions with existing platforms such as QuickBooks, HubSpot, and more
  • Lead a small team of technical professionals, providing guidance and mentorship
  • Manage the technical hiring process as the company scales
  • Develop and maintain the company's AI tooling stack, including Claude API, Make.com, and Clay
  • Build and maintain the internal systems that power delivery
  • Develop and maintain client-facing portals and delivery infrastructure
  • Conduct ongoing maintenance, optimization, and evolution of client AI systems
  • Collaborate with cross-functional teams to drive business outcomes

What We Are Looking For

  • 8+ years of engineering experience shipping real SaaS products
  • Experience with AI-native workflows, including Cursor, Claude API, and Make.com
  • Proven track record of leading small teams and driving technical strategy
  • Strong business acumen, with the ability to think in business outcomes, not just code
  • Experience with HubSpot and other CRM platforms
  • Strong communication and collaboration skills
  • Ability to work in a highly autonomous environment
  • Strong problem-solving skills, with the ability to think creatively

Nice to Have

  • Experience as a founding engineer or technical co-founder
  • Experience with AI-powered tools and platforms
  • Knowledge of business operations and management
  • Experience with agile development methodologies

Benefits and Perks

  • Competitive base salary (
    60,000 - $200,000)
  • Founding-level equity (4.5%)
  • Fully remote work arrangement
  • Comprehensive health insurance
  • Generous PTO policy
  • Professional development opportunities
  • Access to cutting-edge AI tools and technologies

How to Stand Out

  • Be prepared to showcase your ability to think in business outcomes, not just code, and highlight your experience with AI-native workflows and HubSpot.
  • Develop a strong understanding of the company's technical stack, including Claude API, Make.com, and Clay, and be prepared to discuss your experience with these tools.
  • Emphasize your ability to lead a small team and drive technical strategy, and highlight any experience you have with agile development methodologies.
  • Make sure to mention the word EFFECTIVENESS and include the tag RMTI5LjEyMS40MC4xNg== in your application to demonstrate that you have read the job post completely.
  • Be prepared to discuss your experience with client-facing portals and delivery infrastructure, and highlight any experience you have with integrating AI solutions with existing platforms.
  • Highlight your ability to work in a highly autonomous environment and think creatively to solve complex problems.

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