Principal Product Manager

Engageware•Burlington, MA

40d•Remote

About The Position

Engageware’s Enterprise Appointment Scheduling platform is the backbone of how leading financial institutions, healthcare organizations, and enterprise brands connect customers to the right person at the right time. As Principal Product Manager, you will own this product line end-to-end — its vision, its roadmap, its AI-powered future, and its business outcomes. This is a senior individual contributor role with outsized influence. You will set the three-year product strategy, engage directly with enterprise customers and executive stakeholders, define how AI transforms appointment intelligence, and drive engineering to build it. If you have ever wanted a seat at the table where product direction is decided — at a company where scheduling sits at the intersection of AI, financial services, and digital transformation — this is it.

Requirements

10+ years in B2B SaaS product management, with at least 3 years owning a product line or platform end-to-end at the Principal or Senior level.
Demonstrated experience building products for enterprise customers in regulated industries — financial services, banking, credit unions strongly
Proven track record of defining and executing a multi-year product strategy from vision through delivery and adoption.
Strong product discovery and validation skills — comfortable with continuous discovery, Jobs-to-be-Done, or comparable frameworks. You know how to build conviction before you build software.
Experience bringing AI/ML-powered features to market — strategic AI product thinking, not just prompting.
Executive-level communication skills: you can align a VP on a hard trade-off and run a customer advisory board in the same week.
Experience driving engineering teams across complex, multi-quarter initiatives in an agile environment.
Based in the United States, with willingness to travel ~15–20% for customer visits and company meetings.

Nice To Haves

Direct experience with appointment scheduling, resource management, or customer engagement platforms.
Familiarity with Salesforce or other CRM platforms as integration contexts (Salesforce Admin certification a bonus).
Background in fintech, retail banking, wealth management, or branch digital transformation.
Technical background (engineering, data science, or architecture) — enough to earn trust in a deeply technical room.
Experience mentoring or leading other product managers.
Familiarity with Microsoft 365 / Exchange, Google Workspace, Zoom, or Teams as scheduling and calendar integration surfaces.

Responsibilities

Own the multi-year product strategy for Engageware’s Enterprise Appointment Scheduling suite, including the core scheduling platform, intelligent routing, resource management, and omnichannel booking experiences.
Define and communicate a compelling product vision to customers, engineering, and executive leadership — grounding decisions in market trends, competitive dynamics, and customer insights.
Make hard prioritization calls with incomplete information; align the roadmap with business goals and customer segment priorities.
Serve as the internal and external voice of the product — in executive reviews, at customer advisory boards, and in prospect conversations alongside sales.
Own the AI roadmap for appointment scheduling — defining where intelligent capabilities create the most customer value: smart routing, predictive availability, conversational booking, capacity optimization, and proactive engagement.
Partner with engineering and data science to evaluate feasibility, make build-vs-buy-vs-partner decisions, and bring AI features from concept to production.
Stay ahead of market and technology trends to ensure Engageware’s platform remains meaningfully differentiated.
Define and validate AI use cases through structured experimentation — not just vision documents.
Engage directly and regularly with enterprise customers — particularly in financial services (retail banking, credit unions, wealth management, mortgage) — through discovery sessions, design partnerships, QBRs, and advisory boards.
Lead structured product validation: form hypotheses, design discovery, and build confidence before committing to build.
Develop and maintain deep expertise in the enterprise appointment ecosystem — how banks and other regulated institutions manage customer engagement, resource scheduling, and digital-to-physical journeys.
Translate complex, ambiguous customer problems into clear, prioritized product opportunities.
Partner with engineering leadership to shape technical direction, resolve architectural trade-offs, and hold the team accountable for quality and delivery.
Drive sprint planning, backlog prioritization, and release management across multiple concurrent workstreams.
Collaborate with UX, product marketing, sales, and customer success to ship products that land well in market — with strong positioning, enablement, and adoption plans.
Define KPIs and success criteria for every major investment; use data to iterate and drive continuous improvement post-launch.
Own the platform strategy for Enterprise Appointment Scheduling — APIs, extensibility, and third-party integrations.
Define the integration roadmap with CRM platforms (including Salesforce), digital banking channels, and workforce management systems — ensuring scheduling data is contextual and actionable.
Shape decisions around multi-tenant architecture, data residency, and enterprise security requirements in partnership with engineering.