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Salary
$180k – $210k per year
Location
Remote/Hybrid
Overview
Company
Impact
Profile match
Sentinel Group is a financial services and employee benefits firm that offers comprehensive wealth planning, retirement consulting, and healthcare administration solutions. Headquartered in Wakefield, Massachusetts, the company helps organizations design and manage holistic benefit packages for their employees. Its specialized advisory teams also provide personal financial planning and investment management to support individual and corporate clients.

Sinclair is seeking an experienced and collaborative product leader to serve as Director, Enterprise Product Management. This leader will manage a team of approximately 5-10 product managers, product owners, and related professionals responsible for product strategy, roadmap, feature / enhancement delivery, lifecycle management, and Tier 2 support of enterprise business applications used across Sinclair's business and corporate units.

The portfolio supports critical capabilities across sales, finance, accounting, legal, content scheduling, broadcast operations, human resources, and other enterprise functions. It includes custom-developed applications, commercially hosted platforms, and software-as-a-service solutions. The Director will translate business priorities into executable product strategies, balance strategic delivery with operational support, and establish consistent product-management practices across a complex, distributed enterprise.

KEY RESPONSIBILITIES

  • Lead and develop the enterprise product-management team, establishing clear roles, decision rights, performance expectations, development plans, and succession plans.
  • Own product vision, strategy, multiyear roadmaps, investment recommendations, backlog priorities, adoption, and lifecycle plans for assigned enterprise applications.
  • Partner with business executives and technology leaders to evaluate demand, define outcomes, resolve competing priorities, and make transparent portfolio tradeoffs.
  • Ensure roadmaps and backlogs appropriately balance new capabilities, regulatory or compliance needs, defects, technical debt, application health, user experience, and Tier 2 support demand.
  • Establish consistent practices for discovery, requirements definition, feature and PBI authoring, acceptance criteria, refinement, estimation, sprint and release planning, UAT, readiness, adoption, and benefit realization.
  • Work across program management, engineering, architecture, quality assurance, data, cybersecurity, infrastructure, and service management to move initiatives from concept through implementation and ongoing operation.
  • Lead the product team's Tier 2 support responsibilities, including functional investigation, issue triage, business-process and configuration analysis, escalation, and coordination through resolution.
  • Define clear handoffs and escalation paths among Tier 1 support, product teams, internal technology groups, and third-party software providers.
  • Coordinate SaaS and software-vendor support cases, hold providers accountable for responsiveness and resolution, and escalate material incidents, defects, service degradation, and recurring issues.
  • Use incident, problem, defect, and support-trend data to drive root-cause analysis, permanent corrective actions, roadmap decisions, and continuous service improvement.
  • Maintain current product, configuration, integration, dependency, support, known-issue, and lifecycle documentation.
  • Communicate product strategy, roadmap, application health, delivery status, support trends, risks, decisions, and outcomes to executive, operational, and technical audiences.
  • Provide product and operational input to statements of work, software agreements, renewals, supplier reviews, and sourcing decisions in partnership with procurement, finance, legal, and technology leadership.

PRODUCT OPERATING EXCELLENCE

  • Oversee Sinclair's product-management operating scorecard and ensure every product team meets defined minimum operating requirements while demonstrating measurable progress toward gold-standard performance.
  • Set expectations and review results for backlog hygiene, sprint readiness, user story authoring quality, first-pass refinement, in-sprint scope stability, and roadmap maturity.
  • Ensure product priorities are reflected through planned sprints; teams maintain sufficient refined work for predictable delivery; and active products maintain current, centrally available roadmaps reviewed at least quarterly.
  • Establish Azure DevOps dashboards and governance routines that make performance transparent, identify systemic constraints, and assign documented improvement actions, owners, and target dates.
  • Use the scorecard as a team and portfolio improvement mechanism rather than as isolated individual quotas; diagnose upstream discovery, stakeholder, dependency, architecture, or capacity issues that may be driving results.
  • Recognize and scale effective practices from teams operating at or near gold-standard performance.

REQUIRED QUALIFICATIONS

  • Bachelor's degree in information technology, computer science, business, engineering, or a related field, or equivalent professional experience.
  • 8+ years of progressive experience in technology, enterprise applications, digital product management, solution management, or a related discipline.
  • 5+ years in product management, product ownership, or solution management, including 2+ years of direct people leadership.
  • Demonstrated experience leading enterprise application products or portfolios in a medium-to-large organization.
  • Experience with custom-developed applications, hosted platforms, and SaaS solutions, including Tier 2 support and vendor escalation responsibilities.
  • Strong command of product strategy, discovery, roadmaps, backlog management, requirements, release planning, product lifecycle management, and production support.
  • Experience working in Agile, Scrum, SAFe, or hybrid delivery environments and applying practices pragmatically to the product and delivery context.
  • Strong executive presence, communication, facilitation, negotiation, stakeholder management, and decision-making skills.
  • Experience managing technical relationships with software vendors, implementation partners, and managed service providers, including service-level commitments and critical escalations.
  • Working knowledge of application architecture, integrations, data, cybersecurity, testing, incident and problem management, and software delivery practices.
  • Demonstrated use of metrics, objectives and key results, or similar methods to improve product, delivery, operational, and team performance.

PREFERRED QUALIFICATIONS

  • Experience in media, broadcasting, advertising, telecommunications, or another operationally complex and geographically distributed organization.
  • Experience with enterprise application modernization, consolidation, rationalization, or retirement initiatives.
  • Deep experience with Microsoft Azure DevOps, Jira, or comparable product lifecycle and Agile planning tools.
  • Product-management, Agile, Scrum, SAFe, project-management, Lean, or Six Sigma certification; advanced degree preferred.

Please note that this position is not eligible for visa sponsorship, including employer sponsorship for an H-1B visa, OPT-STEM employment, etc.

Sinclair is proud to be an equal opportunity employer and a drug free workplace. Employment practices will not be influenced or affected by virtue of an applicant's or employee's race, color, religion, sex (including pregnancy, gender identity, and sexual orientation), national origin, age, disability, genetic information, military or veteran status or any other characteristic protected by law.

About Sinclair:

Sinclair, Inc. (Nasdaq: SBGI) is a diversified media company and a leading provider of local news and sports. The Company owns, operates and/or provides services to 177 television stations in 79 markets affiliated with all major broadcast networks; owns Tennis Channel, the premium destination for tennis enthusiasts; and multicast networks CHARGE, Comet, ROAR and The Nest. Sinclair’s AMP Media produces a growing portfolio of digital content and original podcasts. Additional information about Sinclair can be found at www.sbgi.net.

About the Team

The life-blood of our organization is our people. We have a compelling story, a goal-oriented culture, and we take really good care of people. How good? Here is a glimpse: great benefits, open-door policy, upward mobility and a strong desire to see you succeed. Ready to be part of a winning team? Let’s talk.

The base salary compensation range for this role is $180,000 to $210,000. Final compensation for this role will be determined by various factors such as a candidate’s relevant work experience, skills, certifications, and geographic location. Full time positions are eligible for benefits that include participation in a retirement plan, life and disability insurance, health, dental and vision plans, flexible spending accounts, 15 paid vacation days, 2 paid personal days, 9 paid holidays, 40 hours of paid sick leave, parental leave, and employee stock purchase plan.

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