VP of Engineering

The VP of Engineering will transform and scale our engineering organization into a highly predictable, elite execution engine. Serving as a strategic partner to the executive team, this leader will establish company-level technical strategy, modernize foundational legacy systems, and translate engineering velocity into business growth at board altitude. The role owns the entire multi-disciplinary engineering domain, including development, quality assurance, and infrastructure, ensuring technical capability aligns perfectly with product priorities. By championing next-generation AI-driven development workflows and cultivating engineering leadership, the VP of Engineering will drive the technological innovation necessary to move core business metrics., * Lead a unified, multi-disciplinary engineering organization focused on operational excellence and a culture of high accountability.

• Partner with product leadership to align technical capacity with product prioritization, creating a reliable, transparent, and repeatable release cadence.
• Direct major enterprise initiatives, including the systematic modernization of the legacy codebase and the integration of AI-assisted tools into daily workflows.
• Achieve and maintain a high sprint and release commitment success rate of greater than 85 percent within the first six months.
• Drive the successful adoption of AI-assisted tooling across engineering and quality assurance teams to achieve a 20 to 30 percent reduction in standard cycle times.
• Deliver a comprehensive codebase refactoring and migration blueprint within 90 days, executing Phase 1 milestones by month nine.
• Transition the quality assurance framework from manual testing to an automated, AI-augmented model that reduces post-release defect escapes by 25 percent.
• Optimize capacity allocation to achieve a target distribution of 60 percent innovation, 20 percent legacy modernization, and less than 20 percent ongoing maintenance by month six.

Do you have experience in Tooling?, Do you have a Master’s degree?, * 10 or more years of progressive software engineering experience, including 4 or more years in a senior engineering leadership role with direct ownership of multiple functions.

• Proven track record leading and scaling engineering organizations in a B2B SaaS company through significant growth or transformation phases.
• Experience partnering at the executive level to translate technical strategy into business outcomes and align investment decisions to company-level growth objectives.
• Experience owning and managing an engineering P&L, including budget planning, headcount allocation, vendor spend, and cloud infrastructure costs.
• Proven experience leading large-scale legacy modernization efforts, architectural refactoring, and service decoupling while maintaining product delivery continuity.
• Hands-on experience with AI-assisted development tooling and a track record of driving adoption and measurable productivity gains across an organization.
• Experience implementing CI/CD pipelines, automated QA frameworks, and metrics programs to drive engineering delivery predictability and quality.
• Exceptional strategic capability, change leadership skills, and a resourcefulness that establishes a strong bias for action across teams.

Skills and Knowledge:

• Familiarity with compliance, legal, or regulated industry software where data accuracy and auditability are core requirements.
• Experience navigating rapid organizational scaling or post-acquisition integration within a private equity-backed environment.
• Deep knowledge of engineering metrics frameworks, such as DORA metrics, cycle time analysis, and defect escape rates.
• Bachelor’s or Master’s degree in Computer Science, Software Engineering, or a related technical discipline.

3.63.6 out of 5 stars Remote $260,000 - $275,000 a year - Full-time, Pulled from the full job description

• Tuition reimbursement
• Parental leave
• 401(k)
• Health insurance
• Paid time off
• Adoption assistance, Harbor Compliance’s base salary range for this role is listed below. Compensation at the time of offer is based on factors such as skill set, experience, qualifications, and work location. Salary is one part of Harbor Compliance’s total compensation package. Other benefits may include health benefits, flexible paid time off, parental leave, fertility and adoption assistance, 401(k), and educational reimbursement. Note that the salary range and benefits apply only to U.S.-based candidates.

Base pay: $260,000 - $275,000 + bonus.

Harbor Compliance is a leading technology platform for entity compliance, helping more than 80,000 businesses and nonprofits manage licensing, tax registration, and legal entity requirements nationwide. Founded in 2012 and recognized repeatedly by the Inc. 5000 and Deloitte Technology Fast 500, we’ve grown through five strategic acquisitions - and are now backed by a 2026 majority growth investment from Bregal Sagemount to accelerate product, AI, and customer experience. We’re a passionate team making compliance simpler and smarter for every organization we serve.