Chief AI Officer - Toronto - Solen Software Group

Description

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 M 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 process. All official communication will come from a verified 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.

Solen-isms (Our cultural rocks)

Pioneering

Pioneering driven by opportunity, using first principles thinking and unbound by tradition or rules.

Mutual Elevation

Committed to growth, elevating teams, developing future leaders, and removing barriers to mastery and joy.

Learn‑It‑Alls

Learn‑it‑alls, not know‑it‑alls, embracing failure as part of growth and progress.

Figure‑It‑Out‑iveness

Embracing challenges, fostering growth, and taking initiative, leaders thrive on hard work and high failure tolerance.

Completionists

We exhibit stick‑to‑it‑iveness. We are Completionists. We adapt. We think long‑term. No plan B. We are all in. We burn the boats.

Ownership Mindset

We own the mission. We don't wait to be told. We lead, fix, and build as if it were ours. When problems arise, we run toward them, not away.

Dialectical

We learn through conversation. We ask, listen, question, and evolve — valuing disagreement as a tool for alignment and deeper understanding.

Benchmark to Best

We seek out excellence. We measure ourselves against the best and adapt quickly, always looking for the edge that moves us forward.

Will to win

Leaders relentlessly pursue potential, reject mediocrity, and get what they tolerate.

Candor

We communicate with integrity, transparency, and respect in all conversations.

Band of beavers

We are relentlessly resourceful, industrious semi-aquatic rodents. Our teeth are self‑sharpening. As multi-faceted generalists, we terraform

Frugality

Achieving more with less, focusing on quality, long‑term value, and company‑wide responsibility.

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