VP, Technology and R&D (AI-DLC Transformation Leader)

Job Description:

VP, Technology and R&D (AI-DLC Transformation Leader)

MiniSoft - Jonas Software

Location: Remote (travel as needed)
Reports to: President, MiniSoft, Inc.
Works closely with: Product, Customer Success/Services, Support, Security/Compliance (as applicable)

Company & Market Context

MiniSoft is a market-leading legal collections software business helping law firms unify collections data, communications, and workflows to improve cash flow visibility and outcomes. Our platform includes ARCS3 (collections/cash flow management) and Acumen (financial insights extending beyond finance to timekeepers).

Role Summary

We are seeking a hands-on, high-impact Technology/R&D leader to own MiniSoft’s engineering execution and modernization with a primary mandate to lead the conversion from SDLC to an AI Development Lifecycle (AI-DLC). This leader will set technical direction, build and scale the delivery system (people/process/platform), and ship AI-enabled capabilities safely and reliably for legal-industry customers.

This role requires demonstrated AI and AI-DLC experience including model evaluation, production monitoring, governance, and the practical steps required to transform an SDLC shop into an AI-DLC shop.

Success Measures (12–18 months)

• SDLC to AI-DLC operating model implemented and adopted across teams (planning, build, eval, release, monitor, iterate).

• Increased delivery throughput and reliability (cycle time down, predictable releases up, fewer production incidents).

• Customer-facing AI capabilities shipped with measurable adoption and trust metrics (accuracy/reliability, time saved, reduced manual effort).

• Internal AI productivity gains realized across engineering/QA, support, services, and go-to-market enablement.

• Strong engineering culture: high standards, strong talent bench, and healthy technical debt trajectory.

Key Responsibilities

• Lead SDLC to AI-DLC transformation: Own AI delivery from intake/data readiness through evaluation, deployment, monitoring, and iteration.

• Governance & trust: Ensure privacy, security, auditability, model/vendor risk controls, and human-in-the-loop use.

• Technical strategy & platform: Drive architecture, data/integrations, QA automation, reliability, and secure engineering (CI/CD, testing, observability).

• Product outcomes: Partner with Product/President to ship measurable, usable, trustworthy capabilities.

• Team leadership: Hire and develop a strong engineering/data/ML org with clear standards and accountability.

• Operational excellence: Improve predictability, capacity planning, tech debt management, and alignment with Services/Support.

What You Bring (Required)

• Senior leadership experience in engineering/R&D (VP/Head/Director+), leading teams that design, ship and operate production software at scale.

• Demonstrated AI delivery experience in a commercial product environment (LLM and/or ML), including evaluation and production monitoring.

• Experience evolving engineering organizations toward AI-enabled product development (AI-DLC, ML lifecycle practices, or similar), including adapting workflows, tooling, and team structures.

• Strong system design and architecture capabilities (data, integrations, security, reliability).

• Track record of improving delivery throughput and quality (CI/CD, QA automation, observability, incident management).

• Executive-level communication skills with the ability to translate technical strategy into clear business priorities and drive alignment across leadership teams.

Strongly Preferred

• Experience in legal tech, fintech, or other regulated/sensitive data environments.

• Experience modernizing legacy systems (cloud migration, platform refactor, API strategy).

• Experience with enterprise security practices and customer trust requirements.

Why This Role

• You will be the technical owner of MiniSoft’s next chapter: AI-enabled product evolution + AI-DLC transformation.

• Significant autonomy and impact, paired with a President-level mandate that explicitly supports this change.

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More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.” We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.