Senior Enterprise Account Executive

Buildings are more complex than ever — and the teams responsible for running them are still working with fragmented tools, disconnected data, and reactive workflows. Willow is changing that. We build the leading Operational AI platform for the built world, helping owners and operators of large, complex environments — think commercial real estate, higher education, healthcare, and airports — better understand, manage, and optimize their buildings by connecting physical, operational, and human data into a unified digital foundation.

Our platform enables customers to move from reactive workflows to smarter operations, better decision-making, and meaningful financial and operational outcomes. We're a small but mighty company with real customers, real traction, and a genuinely important problem to solve — scaling commercial momentum and building the foundation for long-term category leadership. If you want to do meaningful work at a company that's defining a category, this is the place.

About the role

Willow is seeking an Enterprise Account Executive primarily focused on higher education and healthcare, particularly academic medical centers. The role will also pursue select opportunities across K–12 education, airports, state, local, and federal government, data centers, and large corporate campuses where complex facilities and operational needs align with Willow’s strengths.

This is an opportunity to help build the Operational AI category and shape how customers think about the future of their operations. You’ll address immediate facilities challenges while developing a broader vision for AI across building and business operations.

We’re looking for someone who understands the realities of the built world and is motivated to move it forward. You’re curious about how organizations work, where their teams and systems are disconnected, and how AI can enable better ways of working. You can earn credibility with a facilities leader on site and build a compelling business case for a CFO.

What you'll do

• Own the full enterprise sales cycle: Lead opportunities from prospecting and qualification through discovery, demonstrations, business case development, procurement, negotiation, close, and upsell.
• Build pipeline and territory strategy: Identify priority accounts and generate opportunities through outbound, partner, and event motions.
• Lead executive discovery: Engage CFOs, CIOs, facilities executives, operations, energy, sustainability, and capital planning leaders to understand their priorities and establish a compelling reason to act.
• Independently pitch and demonstrate Willow: Connect Willow’s vision and platform capabilities to specific customer challenges through clear presentations and tailored product demonstrations.
• Build credible business cases: Quantify benefits and help customers justify investment within budget constraints and demonstrate measurable outcomes.
• Navigate complex procurement: Understand public sector budget calendars, funding sources, approval requirements, and purchasing pathways. Coordinate RFP responses and work with procurement teams, resellers, and partners to move agreements forward.
• Develop champions and alignment: Build support across stakeholder groups and guide opportunities through IT, security, procurement, and legal reviews.
• Manage deals with discipline: Run each opportunity like a project, coordinating customer stakeholders and internal teams through extended sales cycles. Maintain clear next steps, accurate forecasts, and strong CRM discipline.
• Get in front of customers: Visit customers in person to understand operational realities and build relationships. Expect to travel approximately twice per month.
• Grow customer relationships: Partner with product, engineering, and deployment teams to ensure a successful handover, then stay engaged with customers to drive adoption and expand the account.

What we’re looking for

Required

• Five to ten years of experience selling complex enterprise SaaS or technology solutions, with a demonstrated record of closing significant enterprise deals
• Experience selling into public sector organizations such as public universities, state and local government, airports, or public healthcare systems
• Familiarity with public sector purchasing processes, including competitive solicitations, budget and funding cycles, cooperative purchasing, and reseller or contract vehicle relationships
• Experience managing long sales cycles, multiple decision-makers, and complex enterprise procurement requirements
• The ability to build trust with senior executives, build rapport with technical stakeholders, and connect technical solutions to financial, operational, and strategic priorities
• Proven ability to independently lead discovery, deliver product demonstrations, develop business cases, and negotiate commercial agreements
• Excellent written and verbal communication, including concise executive correspondence, compelling proposals, and the ability to explain technical concepts in business terms
• Strong organization and project management skills, with the discipline to keep complex opportunities moving
• Proven, hands-on use of AI in your own work and the ability to speak knowledgeably about it with customers

Strongly preferred

• Knowledge of building management systems (BMS), building information modeling (BIM), CMMS/IWMS, IoT, smart buildings, energy, construction, or facilities management
• Experience with large corporate campuses as an additional vertical
• Experience working with channel partners, including Carahsoft, Microsoft, and HPE

How you work

• Ownership and accountability: Work independently, exercise sound judgment, and follow through on commitments.
• Initiative and urgency: Anticipate next steps, follow up proactively, and maintain progress toward customer decisions and business outcomes.
• Drive and resilience: Set high standards, remain effective through setbacks, and apply lessons learned to improve performance.
• Openness to feedback: Seek input, recognize where additional expertise is needed, and respond constructively to coaching.
• Adaptability: Work effectively in a growing company, adjust to changing priorities, and help establish repeatable processes.
• Customer focus: Listen carefully, ask thoughtful questions, and develop a practical understanding of customers’ operational demands and resource constraints.
• Cross-functional collaboration: Build productive relationships and coordinate work across teams without relying on direct authority. Communicate clearly in a remote environment and work effectively across time zones and working styles.

$260,000 – $290,000 OTE

$130,000 – $145,000 base salary|50/50 base/commission split|Commission uncapped| Exact offer reflects experience

HEALTH COVERAGE

100% of employee premiums covered; 95% of dependent premiums covered by Willow.

RETIREMENT

401(k) with 100% company match on the first 5% of contributions.

TIME OFF

20 days accrued vacation + 10 days paid sick leave + 8 paid holidays per year.

PARENTAL LEAVE

Willow-paid parental leave, coordinated with applicable state leave programs.

TRAVEL

Approximately twice per month for customer visits. Travel expenses covered.

REMOTE

Fully remote. Dallas/Austin, TX preferred. Open to candidates in WA, TX, NY, CA, NC, NV, MI, MA, MD, IL, GA, or FL.

In accordance with applicable state pay transparency laws, the salary range and a general description of all benefits and other compensation have been disclosed herein. Actual compensation will be determined based on experience, skills, and other relevant factors.