Senior (Principal) Product Manager

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. Medical, Dental & Vision Insurance Flexible Spending Short & Long Term Disability Insurance Company Paid Life & Voluntary Life & AD&D Insurance 401(k) matching 11 Days Observed Holidays 20 Days PTO 5 Days Paid Sick Time Opportunities for career development and growth A collaborative and supportive team culture