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Overview

Solen-isms (Our cultural rocks)

Job Title: Chief AI Officer / AI Enablement Lead (Vertical Market Software)

Company: Solen Software Group

Location: Multiple locations (Toronto, Utah or Lisbon)

Employment Type: Full time

About Solen Software Group

Solen Software Group is an evergreen holding company that acquires and operates proven software businesses that have significant growth potential in a variety of vertical markets, enabling them to be market leaders in their niche industry. Solen owns several software companies in various market spaces: Human Resource Technology, Fleet Telematics, Asset Management, E-Health, Document Management, and other innovative software solutions in a variety of industries. Solen is backed by a group of advisors and investors that have built software businesses of material scale (10-100M in ARR) and advised many.

About This Opportunity

As our Chief AI Officer you will be responsible for identifying, scaling, and operationalizing practical AI use cases across a portfolio of vertical market software (VMS) businesses. This role emphasizes ROI-driven AI adoption, product enhancement, internal efficiency, and repeatable AI patterns that can be deployed across multiple operating companies—while respecting decentralized ownership and autonomy. This is not a centralized R&D; role. Success is measured by measurable business impact, speed to value, and adoption at the operating company level.

Responsibilities

- AI Strategy & Value Creation
- Define and execute a portfolio-wide AI strategy aligned with long-term value creation, customer retention, and operational efficiency.
- Identify high-impact AI use cases across products and internal functions (e.g., pricing, customer support, forecasting, churn reduction, compliance, and workflow automation).
- Prioritize AI initiatives based on ROI, feasibility, data readiness, and repeatability across verticals.

- Product & Platform Enablement
- Partner with operating company product leaders to embed AI into existing VMS products (not rebuild them).
- Develop shared AI patterns, frameworks,



and reference architectures that can be reused across portfolio companies.
- Support build vs. buy decisions for AI tools, models, and platforms.

- Operating Company Support (Decentralized Model)
- Act as a trusted advisor to CEOs, CTOs, and product leaders at portfolio companies.
- Enable adoption without imposing centralized control; influence through frameworks, playbooks, and proven results.
- Provide hands-on support for early AI pilots and transitions to production.

- Data, Governance & Risk
- Establish pragmatic AI governance standards covering data privacy, security, model risk, and regulatory compliance (e.g., SOC 2, GDPR where applicable).
- Ensure AI solutions are explainable, auditable, and appropriate for mission-critical software environments.
- Promote responsible AI use consistent with customer trust and long-term ownership values.

- Talent & Capability Building
- Build internal AI literacy across the portfolio through training, playbooks, and best practices.
- Support hiring, evaluation, and development of AI-related talent at the operating company level.
- Partner with engineering and analytics teams rather than creating a large centralized AI org.

- Success Metrics
- Tangible EBITDA impact or cost savings from AI initiatives
- Product adoption and customer value realized from AI-enabled features
- Repeatable AI use cases successfully deployed across multiple portfolio companies
- Speed from idea → pilot → production
- Operating company satisfaction and voluntary adoption

Qualifications

- 5+ years experience in software, data, analytics, or AI-related roles, ideally in B2B SaaS or vertical market software
- Proven experience delivering production AI solutions with measurable business outcomes




- Strong understanding of modern AI/ML approaches (LLMs, predictive models, automation, analytics), without over-indexing on hype
- Experience working in decentralized, multi-company, or PE-backed environments
- Ability to translate technical concepts into business value for non-technical leaders

Nice to have

- Experience in vertical market software (ERP, industry-specific SaaS, mission-critical systems)
- Background in product management, platform engineering, or analytics leadership
- Familiarity with long-term buy and hold models
- Exposure to regulated industries

Personal Attributes

- Highly pragmatic, ROI-focused, and execution-oriented
- Comfortable influencing without authority
- Long-term thinker aligned with permanent capital ownership models
- Low-ego collaborator who respects operating company autonomy
- Bias toward simplicity, maintainability, and durability over experimentation for its own sake

We thank all applicants for their interest; however, only those selected for an interview will be contacted.

Recruitment Disclaimer

Solen Software Group will never request payment, banking information, or other sensitive personal or financial details during any stage of the recruitment process. All official communication will come from a verified @solensoftware.com email address. Any outreach outside these standards should be disregarded and reported to us through our official channels.

Solen Software Group is a performance-oriented organisation that values career advancement, internal development, and transparent practices. We are an equal opportunity employer and are committed to creating an inclusive, welcoming environment for all team members. We do not discriminate based on race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other legally protected status. All qualified applicants will receive consideration for employment without regard to any of these characteristics.

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Apply on Kit Job: kitjob.ca/job/2fs07b

📌 Chief AI Officer (Toronto)
🏢 Solen-software-group
📍 Toronto