Vice President, Commercial Strategy & Enterprise Deals chez Willowinc

We’re looking for a Vice President, Commercial Strategy & Enterprise Deals — a senior leader who can both architect our monetization model and negotiate directly with customer C-suites. This role combines commercial strategy, enterprise negotiation, and public sector contracting expertise. You’ll be Willow’s commercial architect and deal leader: designing pricing and packaging, modeling complex SaaS agreements, managing procurement pathways, and ensuring contracts meet the high standards of enterprise and public sector compliance. 

What You'll Do

Represent Willow in C-suite negotiations with major universities, healthcare systems, airports, and real estate customers. 

Structure and close multi-year SaaS agreements that balance customer value with Willow’s growth and margin objectives. 

Serve as the commercial authority in strategic deals, alongside Sales and Growth leadership. 

Design pricing and packaging across our SaaS portfolio, including Software, Professional Services, AI add-ons, and maintenance. 

Model enterprise agreements for P&L impact, risk, and long-term value creation. 

Build repeatable playbooks that align Sales, Product, and Finance around scalable commercial structures. 

Draft, review, negotiate, and manage contracts with vendors, service providers, and public agencies. 

Ensure compliance with company policies, legal standards, and public sector procurement regulations (federal, state, and local). 

Maintain a centralized contract repository, tracking expirations, renewals, and compliance obligations. 

Navigate procurement pathways specific to government and education clients (e.g., GSA schedules, state cooperative contracts, education sector vehicles, FAA compliance for aviation). 

Develop expertise in government procurement rules, grants, and GASB/OMB standards. 

About You

12+ years in commercial strategy, enterprise deal-making, SaaS monetization, and contract management. 

Direct experience leading C-suite negotiations on $5M+ enterprise or public sector contracts. 

Deep knowledge of SaaS pricing, SKU architecture, and packaging strategies. 

Hands-on expertise in contract law, procurement, and public sector compliance (federal, state, local). 

Strong financial acumen; confident modeling P&L and long-term portfolio economics. 

Executive presence — credible across from Fortune 500 and public agency leadership. 

Bonus: experience in education, healthcare, airports, or real estate SaaS. 

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