Professional Services Program Manager

The Professional Services, Program Manager, Strategic Enterprise Implementation owns the day-to-day operating cadence for a single, large-scale, multi-site enterprise implementation program. They will be the point person on a program that spans dozens of locations, multiple rollout phases, and a multi-year timeline. This role keeps a high-stakes program moving by driving stakeholder engagement, tracking dates and milestones, running meetings, maintaining the risk and action-item log, and routing blockers to the right internal team. Success means the program never loses momentum, and every team stays pointed at the same goals, and nothing falls through the cracks at scale. Program Cadence & Coordination • Own the recurring meeting cadence for the program (core team check-ins, working group sessions, leadership reviews) - scheduling, agendas, and follow-through. • Take and distribute notes from program meetings, ensuring decisions and commitments are captured and visible to all stakeholders. • Maintain the master roadmap and milestone tracker, keeping phase dates, go-live targets, and dependencies current and visible. • Keep the program's shared documentation (trackers, plans, contracts-in-progress, status pages) accurate and up to date. Team Alignment & Momentum • Keep every workstream and team both internal and customer-side, oriented around the program's shared outcomes and goals, not just their own slice of the work. • Proactively check progress against plan at the scale this program demands (hundreds of concurrent or sequenced venues), catching slowdowns before they compound across waves. • Re-align teams quickly when priorities shift, a date slips, or a workstream drift from the agreed plan - don't wait for the next scheduled check-in to course-correct. • Keep cross-functional partners (Sales, Legal, Product, Engineering, Customer Success) and the customer's team rowing in the same direction, even as the program moves through different phases and waves. Stakeholder Engagement • Serve as the connective tissue between the customer's stakeholders and internal teams (Sales, Legal, Product, Engineering, Customer Success). • Build and sustain engagement with customer-side points of contact across a large, often multi-entity organization. • Prepare and deliver regular status updates and executive summaries tailored to customer and internal leadership audiences. Risk & Action Item Tracking • Maintain a living risk and blocker log; proactively flag items that threaten timeline, scope, or sentiment. • Track open action items to closure, chasing owners and escalating when dates slip. • Distinguish between items the program can resolve directly and items that need escalation (technical, commercial, or legal) - and make sure escalations land with the right owner. Cross-Functional Escalation & Routing • Route technical blockers (e.g., integrations, data migration, identity/access, payment processing) to Product and Engineering with enough context for them to act. • Coordinate with Sales and Legal on contract and scoping timelines that gate program sequencing. • Flag when a program risk needs leadership visibility or a decision above the program manager's authority. Executive Reporting & Visibility • Own the recurring executive reporting rhythm for the program; both internal (to company leadership) and customer-facing (to the customer's executive sponsors). • Build and deliver internal executive updates that give leadership a clear, honest read on scope, timeline, risk, and sentiment, so decisions and support can happen before issues become urgent. • Build and deliver customer-facing executive summaries that keep the customer's sponsors confident in the program's progress, written to maintain trust even when flagging risk. • Tailor message and level of detail to each audience: leadership needs the headline and the ask; the customer executives need the narrative and the reassurance, while keeping the underlying facts consistent across both. • Keep a single source of truth for program status that both the customer and internal leadership can reference formal updates. Requirements • 4+ years in program or project coordination, implementation management, or customer-facing delivery roles in an enterprise B2B SaaS environment. • Experience coordinating complex, multi-stakeholder, multi-phase programs at scale (hundreds of sites/locations), comfortable managing many moving parts without owning the underlying technical work. • A track record of keeping large, cross-functional efforts aligned and moving with the ability to spot drift early and re-rally teams around the program's goals rather than letting momentum stall. • Strong organizational skills: scheduling, documentation, and follow-through are core to this role, not an afterthought. • Excellent written and verbal communication; able to translate technical or commercial detail into clear updates for varied audiences. • Comfortable engaging with technical topics (system integrations, data migration, identity/SSO, payment processing) at a coordination and escalation level, without needing to build the solutions directly. • Experience working cross-functionally with Sales, Legal, Product, and Engineering to keep a program unblocked. Important Notice on Location Eligibility: This is a U.S.-based remote role. However, due to regulatory requirements, we are only able to consider candidates who reside in U.S. states that do not currently mandate salary disclosure in job postings. Candidates residing in California, or other states with active pay transparency laws will not be considered at this time.