Role: Senior Engineer, Technology Lead
Compensation: $170,000 - $200,000/year
Location: Naugatuck, CT
Reports To: COO
We’re hiring a Senior Engineer, Technology Lead – this is a senior role with a broad scope: technology roadmap, software and systems architecture, AI strategy and governance, vendor and partner management, security and compliance, and operational technology oversight. The Senior Engineer, Technology Lead works directly with the executive leadership team as a peer on technology decisions and serves as the most senior technology voice in the company.
As The Next Street accelerates the use of AI-assisted development across teams and vendors. AI tooling has dramatically lowered the cost of building software – but not the cost of validating architecture, ensuring maintainability, or managing operational risk, and this role exists to close that gap. This role is built for a hands-on technologist – someone with a software engineering background who has moved beyond writing code full-time but still thinks like a builder, being equally comfortable reviewing vendor’s architecture, prototyping a small internal tool, debating a contract clause, or briefing the CEO on AI risk. They are genuinely excited about where AI is heading and eager to dive deep into it as a core part of the role.
This role may suit someone earlier in their senior career – curious, pragmatic about established systems, and energized by newer AI-driven approaches.
Tasks and Deliverables:
Develop and own a multi-year technology strategy and roadmap aligned with company growth and operational needs
Lead architectural decisions across internal systems, including evaluating code quality, system design, and integration approaches
Establish development standards, code review processes, and deployment readiness criteria for AI-assisted work across the company – including standards for staging, testing, rollback, and production release
Serve as the independent technical validator on vendor and internal work – with authority and responsibility to escalate or block production releases when quality, security, or operational risk warrants it
Build and prototype where it adds value – small tools, integration, automatons, and proofs of concept that demonstrate what’s possible and unblock decisions.
Own AI strategy and governance end-to-end, including tool selection, policy maintenance, evaluation of new AI capabilities, and responsible adoption across the organization
Evaluate and manage technology vendors and partners, including contract review, SOW negotiation, ongoing performance accountability, and serving as a technical counterweight to vendor recommendations when needed
Oversee the relationship with the managed service provider on day-to-day IT operations while owning the strategic technology layer above it
Translate technical complexity into clear business decisions for non-technical stakeholders
Required Qualifications:
5-8 years of progressive experience that includes hands-on software engineering and a clear move toward technical leadership, architecture, or strategy
Demonstrated ability to build software – not just review it – even if production coding is no longer your day-to-day
Hands-on experience using modern AI tools in a real work context (Claude Code, Cursor, GitHub, or similar), with a clear point of view on responsible AI adoption
Working familiarity with modern web stacks (React, Next.js, Node, Phyton, Postgres, cloud- services) and the Microsoft ecosystem (Power Platform, Dataverse, Azure, SharePoint), with the ability to evaluate code produced with them
Sound judgment on architecture, security, scalability, and operational resilience – able to spot fragility, technical debt, and risk in systems built by others (including AI-assisted output)
Comfortable balancing established proven technology with newer AI-driven approaches – and knowing when each is appropriate
Demonstrated experience evaluating, managing, or working closely with technology vendors and contractors
Experience establishing or operating within technical review, deployment, or release processes
Vendor management and contract negotiation skills, with the confidence to challenge vendor recommendations when the technical judgement calls for it
Excellent communication, with the ability to translate between technical and business audiences
Bachelor’s degree in Computer Science, Information Technology, or a related field or equivalent professional experience.
Authorization to work in the U.S.
Nice to Have:
Benefits:
Medical, Dental & Vision (FT)
401k (Employer Matching)
120 Hours of Paid Time Off
40 Hours of Paid Sick Leave
Paid Holidays and more!
About The Next Street
The Next Street is a driving school unlike any Driver’s Education school you have seen before. We put a huge effort into surrounding ourselves with friendly, happy, energetic, and all-around good people. We hire great people and teach them the skills they need to be outstanding. We believe in helping you become the best version of yourself. We believe in you and want to help you achieve your career goals (and support you in your personal goals). We believe in creating a team environment with like-minded peers that support each other and make you feel a part of something bigger than yourself.
Our staff is a diverse community of people, all connected by our belief in 3 core values: Kindness, Positivity and Curiosity. No member of our staff is a cog in the wheel. We are all (from the CEO to our Licensing Guides to Managers to Instructors and everywhere in between) a part of something bigger than ourselves and we work together to serve the greater good.
How to be Successful:
We pride ourselves on cultivating a team of inspired and dedicated individuals who embrace our core values both professionally and personally. All non-negotiable.
Just Be Nice: Be a good co-worker, be a good neighbor, be a good human.
Think Positively: The glass is always half full. Positive mindsets will lead to positive outcomes.
Be Curious: Seek to be more valuable tomorrow than you are today. Look for training opportunities, not only in formal education settings, but in the everyday course of business and in life.
At The Next Street we like to surround ourselves with individuals who are curious and inquisitive by nature. People that are hungry for knowledge and continually find ways to make improvements. Streeters don’t just get the job done, they do a great job. The Next Street Team isn’t cordial and polite – they are genuinely nice. It is in their nature; they don’t have to work at it.
