Job Specifications
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.
Key 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
Our ideal Candidate
Key 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 but not mandatory
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 p