Product Manager — Product Modernization

InRule; Chicago (IL); On-site; USD 100,000 - 130,000; Full time

Job summary

A technology firm in Chicago is seeking a Senior Product Manager to lead the modernization of their product suite. In this role, you'll simplify complex workflows to enhance usability for non-technical users while ensuring product reliability. You will own the product roadmap, collaborate with cross-functional teams, and drive market understanding through comprehensive user research. The ideal candidate has 5+ years of B2B product management experience with a proven ability to manage product rollouts effectively.

Qualifications

• 5–10+ years of B2B product management experience.
• Experience in simplifying complex workflows.
• Experience modernizing products with careful rollout strategies.

Responsibilities

• Own the product roadmap for modernizing products.
• Lead discovery to identify where complexity exists.
• Ensure modernization improves product efficacy.

Skills

Product management experience

Ability to simplify complex workflows

Strong communication skills

Prioritization and outcome measurement

Job description

About the role

You will lead the evolution of a mature, mission-critical product suite—simplifying powerful capabilities so more users can succeed, while preserving the reliability and behavior our customers depend on.

This is a senior individual contributor role with significant influence and cross-functional leadership responsibility. You’ll work within our Outcome-Driven Innovation (ODI) practice, using a Jobs-to-Be-Done approach to ground roadmap decisions in measurable customer outcomes.

The Challenge

InRule’s products are deeply embedded in customers’ critical workflows. Over time, their power and flexibility have accumulated complexity, resulting in software that works well for technical users but can be difficult to learn and operate for non-technical business users.

Modernizing the platform for SaaS and AI is one part of the work; the more important part is making powerful functionality easier to understand and use by non-technical business users, while preserving the behavior and reliability existing customers depend on.

The hardest part of the work is not the technology, it’s deciding what to simplify, redesign, or leave alone, and doing so in a way that earns customer trust and expands ARR.

What you\'ll do

• Own the product roadmap for modernizing long-standing products with a primary focus on improving usability and the use of AI by non-technical end users across their journey, from onboarding to day-to-day use.
• In scope: rule authoring user experiences, operability and governance workflows, SaaS readiness and safe customer migration patterns. Out of scope: platform infrastructure and the architectural design of rule execution.
• Lead discovery to identify where complexity exists today, why it exists, and which capabilities can be simplified, redesigned, or removed.
• Ensure modernization efforts measurably improve product efficacy, including usability, reliability, performance, security, data sovereignty, and cost-to-serve.
• Partner with Product Design to deliver high-clarity experiences for complex workflows.
• Establish instrumentation to measure adoption, user success, and changes in product usability with a focus on time-to-first-value.
• Support market understanding through user research, win/loss analysis, and competitive analysis.
• Work with Product Marketing and Customer Success to enable customer adoption and migration, clearly communicate change, and maintain trust through transitions.
• Serve as a product voice with customers, including launch partners and analysts.

What success looks like

• Reduced time-to-first-value for new users (onboarding + first successful configuration)
• Higher task success rates and fewer “expert-only” or IT bottlenecks
• Fewer support escalations tied to configuration and usability
• Reliability and security posture improved throughout modernization

What we\’re looking for

Required

• 5–10+ years of B2B product management experience
• Ability to simplify complex workflows into intuitive experiences, without removing critical power
• Experience modernizing long-lived products with careful rollout and migration strategies
• Strong discovery, prioritization, and outcome measurement, qual and quant
• Excellent communication across technical and non-technical audiences

Preferred

• Experience in regulated or high-reliability environments
• SaaS modernization (multi-tenant, security, observability, cost-to-serve)
• AI product experience, especially assistive UX patterns with governance

How we work

• Outcome driven innovaiton and JTBD-informed discovery and prioritization
• Close partnership with Design, Sales and Engineering
• Customer-informed iteration and trust-preserving rollouts
• Take the time to make things simple for users and teammates