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Director, Asset Strategy

Salary: $120K + you’ll become a shareholder in our company and earn equity.

Benefits: FREE employee-only medical coverage under one of our plans. FREE short-term disability and FREE life insurance coverage. Plus, a 4% employer match with our 401(k). Other incredible benefits HERE.

Location: NYC or San Francisco, remote work with some travel

Reports to: Executive Leadership

The Director of Asset Strategy is responsible for leading the execution of Advisory engagements, ensuring that Playbook delivers best-in-class consulting and strategy work that consistently exceeds client expectations. Acting as the project lead, this role manages timelines, client communications, and cross-departmental inputs, ensuring deliverables are completed on time, on budget, and with measurable client impact.

You'll Know You're Successful If:

• Client Satisfaction: 90%+ client satisfaction score (measured through surveys and direct feedback)
• Advisory Delivery: 100% of Advisory projects delivered on-time, in-scope, and on-budget
• Client Growth: 110% Net Recurring Revenue (NRR) retention across Advisory accounts

What You'll Do:

• Lead the end-to-end management of Advisory projects, ensuring deliverables are completed with excellence and alignment to client objectives.
• Build and manage project plans, timelines, and accountability structures across Playbook teams (design, placemaking, operations, marketing, technology).
• Facilitate cross-departmental collaboration, ensuring inputs from multiple leaders are streamlined into cohesive, client-ready outcomes.
• Track risks, issues, and dependencies—proactively problem-solving to maintain project momentum.
• Serve as the day-to-day client lead during Advisory projects, building trust with ownership, asset managers, and property teams.
• Translate complex client needs into actionable project goals and communicate progress with clarity and confidence.
• Navigate client dynamics with professionalism, fostering long-term trust and positioning Playbook as a strategic partner.
• Act as a thought leader for clients on placemaking, hospitality trends, and tenant engagement best practices.
• Identify opportunities to extend Advisory engagements into management and operations partnerships.
• Collaborate with business development and operations leaders to structure proposals and secure long-term contracts.
• Contribute to upsell strategies, renewal planning, and client business reviews.
• Track client health across a portfolio of accounts; proactively flag risk and align internal teams on retention plans.
• Lead quarterly business reviews (QBRs) and strategic planning sessions with VIP clients and executive decision-makers.
• Partner closely with VP of Design & Development and VP of Placemaking to align strategies and ensure delivery excellence.
• Act as the connective tissue across departments, ensuring Playbook teams are aligned on client expectations and accountable for their deliverables.
• Support knowledge-sharing and best practices across the Asset Strategy department.

Who You Are - Key Competencies:

• Obsessively client-centric: You prioritize partner needs, ensuring their success and fostering long-term relationships. You build deep trust with diverse personalities and organizational structures and understand unspoken needs, power dynamics, and political nuances.
• Executive Presence & Communication: You are a clear and confident communicator who can lead strategic conversations with ownership groups, asset managers, and C-suite clients. Your polished presentation skills for strategy sessions, and internal leadership meetings always leave a lasting impact.
• Embody our brand: You represent Playbook with professionalism and expertise, building trust and championing our brand mission and values.
• Strategic thinker: You make data-driven decisions with a long-term focus to drive customer and business growth. You connect the dots across operations, design, marketing, and programming to craft holistic amenity solutions. You bring a consultative mindset—you ask great questions, seek to understand context, and balance vision with practicality.
• Cross-functional collaboration: You bring departments together to solve problems and align around a common client outcome.

Who You Are - Baseline Qualifications:

• 6+ years of experience in client success, account strategy, or consulting—preferably within commercial real estate, workplace experience, or hospitality services across multiple locations or properties.
• Strong understanding of customer lifecycle management, retention models, and client health monitoring frameworks.
• Executive presence with excellent communication and presentation skills; experience leading client business reviews with C-suite audiences.
• Strategic thinker with a strong analytical foundation; ability to interpret data, drive actionable insights, and guide the client based on project goals.
• Experience influencing product and operational teams through the voice of the customer.
• Proven ability to lead executive-level client relationships and deliver measurable outcomes across multiple sites or asset types.
• Deep knowledge of amenity strategy, tenant engagement, and operational excellence in CRE environments.
• Proven ability to manage high-visibility, client-facing projects with rigor: building project plans, facilitating cross-functional workstreams, and ensuring on-time, high-quality delivery aligned to strategic client objectives.
• Confident facilitator and communicator with experience leading strategic conversations and business reviews with C-suite stakeholders.

Playbook's culture is based on a shared respect for our lived values HERE. Fit with our values is a critical component of our hiring process, and you and all of our colleagues are expected to live our core values in interactions with team members, customers, and stakeholders. An assessment of how you have exhibited our values is also an important part of your performance review process.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.