Senior Director - Product and Strategy

Senior Director, Product & Strategy – Associations 

Overview 

Product & Strategy Leaders are the quarterbacks of their business, accountable for product stability, growth, profitability, customer experience, and innovation. In full partnership with our Engineering, Revenue, and Operations counterparts, they are responsible for leading their portfolios with purpose, precision, and pride. 
 
We are raising the bar. Expectations are high because our customers and the markets we serve deserve nothing less. These roles require an exceptional blend of strategic thinking, operational rigor, and relentless follow-through. Hard work is the norm, not for recognition, but for the greater good of our customers and the long-term health of our company. 
 
Each leader owns a defined portfolio and ensures its health, trajectory, and outcomes are visible, measured, and trending in the right direction. When results are off track, they act swiftly, diagnosing root causes, aligning cross-functional partners, deploying countermeasures, and escalating to the ELT when required. 
 
Success in these roles depends on collaboration. Product & Strategy leaders partner deeply with Finance, Revenue, Engineering, CX, Operations, Legal, and Pricing Strategy. They engage directly with customers, represent the company externally, and anchor decisions in data, empathy, and accountability. 
 
Beyond their portfolio, each leader contributes to the strength of the entire Product & Strategy organization. They step up for cross-functional projects, model professionalism, and engage in healthy debate with positive intent and transparency. They understand that sometimes the best outcome for the company is enabling another portfolio to win. 
 
We are a team that learns fast, adapts faster, and embraces innovation, especially through the responsible use of AI to enhance our efficiency, insight, and customer impact. Together, we are shaping the future of our markets, our company, and our customers’ success. 
 
At the Senior Director level, this means translating strategy into disciplined execution—driving measurable impact while maintaining transparency, collaboration, and operational excellence. 

Role Summary 

Leads the Association sub-vertical, focused on platform migrations, retention, and modernization. Responsible for delivering customer stability while driving future-state improvements aligned to the broader Associations, Fraternal, and Nonprofit portfolio. 

Scope & Strategic Focus (OLPIS-Aligned) 

• Leads: Roadmap, migration execution, and Tier 3–4 initiatives.
• Partners: With Engineering, Revenue, and CX on migration plans and preparation of proposals for company-level reviews.
• Supports: VP with portfolio data and updates for ELT review.
• Informed: Communicates progress, risks, and countermeasures to key stakeholders. 

Span of Leadership & Influence 

Product Managers, Product Owners, Delivery Manager, Contractors. 

Key Responsibilities 

• Lead Association product migrations, ensuring successful transitions with minimal churn.
• Govern roadmap features and delivery within allocated resources, ensuring customer stability and product modernization.
• Support VP in the development of business cases and proposals for company-level review and approval.
• Host quarterly customer webinars and publish migration-focused roadmap updates for transparency.
• Partner with Engineering, Revenue, and CX to manage risks and proactively address delivery challenges.
• Participate in monthly and quarterly business reviews (MBRs/QBRs) to assess performance, identify opportunities, and communicate adjustments.
• Lead de-risking and countermeasure planning for key initiatives.
• Manage customer escalations as the near-final resolution point before ELT involvement.
• Analyze competitive market movements and collaborate with Pricing Strategy on packaging models.
• Model Togetherwork’s leadership principles of positive intent, professionalism, and accountability. 

Strategic & Financial Accountability 

• Accountable for execution of Tier 3–4 initiatives within lifecycle-based resource allocations.
• Partners with VP and Finance to align resource planning and performance metrics with business outcomes.
• Contributes to the preparation of proposals for larger initiatives requiring company-level approval.
• Participates in monthly and quarterly business reviews (MBRs/QBRs) to track progress, report results, and propose adjustments. 

Customer & Market Engagement 

• Hosts quarterly webinars and publishes migration-progress roadmaps.
• Engages with customers to collect feedback and assess migration experience quality.
• Serves as the near-final escalation point for unresolved issues.
• Partners with CX and Revenue teams to ensure that customer insights directly inform roadmap priorities. 

Leadership & Team Development 

• Coaches and develops everyone within the Associations product organization.
• Promotes transparent communication, accountability, and continuous improvement.
• Encourages AI and analytics usage to improve decision-making and predict performance outcomes. 

Key Metrics / Success Measures 

• Migration completion rate, NPS, and customer retention.
• Improvement of delivery velocity and roadmap predictability.
• Quarterly roadmap publication and webinar cadence.
• Team engagement and 360 feedback improvement. 

Travel Expectations 

25%+ for leadership meetings, customer engagement, and migration planning sessions.

Standout Skills 

• Product Management tenure in a SaaS or enterprise software industry.
• Extensive knowledge of association management software.
• Experience working with or within associations, trade organizations, or professional societies.
• Proven experience in establishing and scaling product management methodologies and processes from the ground up.  
• Strong understanding of Salesforce and/or Microsoft Dynamics platforms.