Remote Msp Engineering Jobs in Chicago, IL (NOW HIRING)

HEAD OF PRODUCT
Strategic + hands-on leadership of our full AI & BI product portfolio

Work Setup: Remote (US-based only)
Work Schedule: Flexible-with regular meetings across PH, US, and China teams

ROLE OVERVIEW
We are seeking a strong, hands-on Head of Product to lead the product function at MSPBots. You will own the end-to-end lifecycle of our AI-powered and BI products-from ideation through launch, iteration, and commercial scale. This is both a strategic and execution-heavy role: you will build and refine our product development and implementation process while driving measurable revenue growth across new and existing MSP clients.

Your portfolio spans our Business Intelligence Dashboards, Micro Training Bots, Next Ticket, Integrations, Featured Apps, and a growing pipeline of AI-powered products-including ticket triage, ticket QA, and sentiment analysis-at various stages from production to alpha launch to future roadmap.

KEY RESPONSIBILITIES
Revenue-Driven Product Leadership

• Own product revenue outcomes-driving both new revenue acquisition and client retention through product value delivery.
• Define and pursue ARR targets tied to product launches, feature adoption, and upsell opportunities across the MSP client base.
• Partner with Sales and Marketing to align product positioning, packaging, and pricing with revenue goals.
• Identify expansion opportunities within the existing client base by deepening product adoption and launching complementary features.

Product Strategy & Roadmap

• Define and own the product roadmap across all product lines: BI Dashboards, Micro Training Bots, Next Ticket, Integrations, Featured Apps, and AI-powered apps.
• Balance short-term commercial priorities (live products, alpha launches) with long-term strategic bets (future AI initiatives).
• Make clear prioritization calls across a mixed portfolio-production support, active launches, and future development-ensuring the team is focused on the highest-impact work.

Product Process - Build & Refine

• Architect and implement a scalable product development and implementation process, from discovery and scoping through QA, release, and post-launch review.
• Establish frameworks for MVP definition, alpha/beta launch management, client feedback loops, and iteration cycles.
• Ensure the product team operates with clarity, velocity, and consistency across all stages of the product lifecycle.

Team Leadership

• Lead, coach, and grow a product team of PMs and BAs, setting clear expectations, priorities, and performance standards.
• Foster a culture of ownership, client-centricity, and data-driven decision-making within the product org.
• Serve as the connective tissue between Engineering, Data Science, Design, Sales, and Marketing.

AI Product Development & Support

• Drive the development, alpha launch, and scaling of AI-powered products, including ticket triage, ticket QA, and sentiment analysis.
• Support ongoing AI projects and future AI initiatives, ensuring they are built with clear use cases, success metrics, and a path to revenue.
• Stay current on AI/ML trends, GenAI capabilities, and the competitive landscape to inform product direction.

Client-Centric Execution

• Engage directly with MSP clients to validate product value, gather requirements, and close feedback loops.
• Ensure all products-especially new AI launches-deliver measurable, demonstrable value that justifies adoption and renewal.
• Oversee documentation, onboarding materials, and training support to enable client success at scale.

Performance & Reporting

• Define KPIs for each product line tied to revenue, adoption, retention, and client satisfaction.
• Report product performance regularly to the CEO with clear insights, risks, and recommendations.
• Use data to drive prioritization decisions and communicate tradeoffs with confidence.

QUALIFICATIONS
Required

• 5+ years of product management experience, with at least 1-2 years in a product leadership or senior PM role.
• Demonstrated success taking AI/ML or GenAI-powered products from concept through launch and commercial scale.
• Strong track record of contributing to revenue growth through products-whether through new launches, upselling, or retention.
• Must have successfully released at least one AI product to production or commercial use
• Experience building or significantly improving product development processes in a scaling environment.
• Strong technical acumen-comfortable working closely with engineering and data science teams.
• Excellent communication and stakeholder management skills, with the ability to align cross-functional teams across the US, China, and the Philippines.
• Analytical mindset with a data-driven approach to decision-making and prioritization.
• Proven ability to manage a mixed portfolio-balancing live products, active launches, and future-state planning simultaneously.
• Experience working in agile environments with multiple competing priorities.

NICE TO HAVE
MSP/IT services industry Azure OpenAI or AWS AI Usage-based billing models

BI/Analytics products B2B SaaS

Ready to build something that changes how MSPs operate? We'd love to hear from you.