Senior – Principal Product Manager
Lakeside Software
Senior – Principal Product Manager
Lakeside Software
Monitors IT end-user experience via SysTrack
Lakeside Software · Ann Arbor, United States (Remote) · Full-time · Posted 2026-09-09
Workplace: remote
Department: Strategy & Products
Lakeside Software is looking for a Senior or Principal Product Manager to own and advance key areas of the SysTrack platform. You will independently take customer and business problems from discovery through delivery, while developing a clear point of view on how the capabilities you own should evolve.
You will work closely with Engineering, UX, Customer Success, Sales, Support, and other product leaders to understand customer needs, set priorities, define requirements, and guide product investments through development and release.
What You'll Do
Own the roadmap, priorities, and backlog for assigned areas of SysTrack
Develop a clear understanding of the customer problems, workflows, and technical capabilities within your product areas
Engage directly with customers and internal teams to identify pain points, unmet needs, and recurring product opportunities
Separate underlying customer problems from requested solutions and validate concepts before significant engineering investment
Translate product direction into clear epics, features, workflows, requirements, and acceptance criteria
Make and communicate tradeoffs between new functionality, customer requests, usability, technical investment, and defects
Partner closely with Engineering and UX throughout discovery, planning, implementation, and release
Make timely product decisions when scope, requirements, or technical constraints change
Ensure individual investments contribute to a coherent SysTrack experience
Represent your product areas in customer conversations, roadmap discussions, and internal planning
Build expertise in Digital Employee Experience, endpoint management, IT operations, and adjacent markets
Contribute to broader product planning and identify patterns that may have implications across SysTrack
What We're Looking For
4–7 years of product management experience, preferably in enterprise software
Demonstrated experience independently owning software features or product areas from discovery through delivery
Strong ability to turn ambiguous customer problems into structured product opportunities and requirements
Sound judgment when balancing customer needs, strategic priorities, technical investment, and delivery constraints
Experience working directly with engineers on technically complex products
Experience engaging with customers and translating feedback into product decisions
Strong written and verbal communication skills
Comfort making decisions with incomplete information and adjusting as new evidence becomes available
Experience with DEX, endpoint management, ITSM, analytics, observability, enterprise AI, automation, APIs, or other data-intensive enterprise software is helpful.
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Monitors IT end-user experience via SysTrack
Lakeside Software provides Digital Experience Monitoring for large enterprises, focusing on improving IT performance and end-user productivity with its flagship SysTrack. SysTrack collects data from endpoints like computers and servers to measure performance and user experience from the user’s perspective, helping IT teams identify issues, optimize resource use, and boost productivity. The product is offered primarily through subscription licenses, and Lakeside also provides consulting services to help organizations implement SysTrack effectively. What sets Lakeside apart is its emphasis on end-user experience and workspace analytics for enterprise environments, combined with ongoing licensing and advisory services to drive IT cost reductions and better performance. The company’s goal is to help organizations reduce IT costs, improve system performance, and enhance user satisfaction by delivering actionable visibility into IT operations.
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