VP of Enterprise Operations

Swooped; United States; On-site; USD 270,000 - 315,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Life insurance

Disability insurance

401(k) with company match

Flexible time off

Wellbeing days

Paid holidays

Summer Fridays

Mental health resources

Paid parental leave

Backup care

Tuition reimbursement

Employee resource groups

Job summary

Swooped seeks a VP of Enterprise Operations to partner with the CEO on how the organization runs at the executive level. You will own the executive operating system, integrated planning, board processes, and AI-native tooling, ensuring decisions are made with visible tradeoffs and commitments are executed.

In this role, you will lead ELT governance, coordinate annual planning and OKRs, manage board materials and inquiries, and drive AI-enabled workflow redesign across the company.

Qualifications

• Minimum 10 years in enterprise operations at a software company.
• Proven board-cycle management with PE/growth investors.
• Experience leading executive-level operating systems and planning.
• Ability to drive accountability and cross-functional alignment.
• Hands-on AI-driven process redesign.

Responsibilities

• Design and operate ELT decision forums with clear accountability.
• Oversee integrated planning spanning long-term goals to quarterly budgets.
• Direct board calendar, materials, and investor communications.
• Own AI-native executive operating system redesign and adoption.
• Lead strategic, time-bound cross-functional initiatives.

Skills

Executive leadership

Annual planning

Board governance

Cross-functional collaboration

AI-enabled operations

Financial literacy

Stakeholder management

Tools

AI tooling experience

OKR software

BI tools

Job description

The VP of Enterprise Operations serves as the CEO's partner for how the organization runs at the executive level, reporting directly to the CEO as a full member of the executive leadership team (ELT). The role owns the executive operating system, integrated planning process, board operating process, and the underlying AI-native tooling. While functional leaders own their results and the CEO and ELT own strategic choices, this role ensures decisions are made on time with visible tradeoffs and that agreed commitments are executed.

Key Responsibilities

• Run the ELT operating system: Design and operate executive decision-making and accountability forums, audit recurring meetings, establish decision rights and commitment norms, maintain the central commitments-and-decisions log, ensure decision items arrive framed with recommendations, and elevate open cross-functional issues to the CEO.
• Own the integrated planning process: Connect company choices into a unified system spanning long-term ambition, annual priorities, departmental plans, OKRs, and quarterly reallocation; manage the calendar, sequencing, and templates to ensure strategic choices precede budget development and reconcile cross-functional plans.
• Run the board operating process: Direct the annual board and committee calendar, agenda architecture, and the integrated narrative across strategy, operating performance, financials, talent, and risk; assemble board materials, prepare executives, anticipate board inquiries, track follow-ups, and coordinate with investors.
• Serve as business owner of the AI-native executive operating system: Redesign executive workflows using AI to improve signal, preparation, decision memory, and accountability across executive briefs, KPI commentary, commitment tracking, decision memos, strategy-to-OKR traceability, board materials consistency, and scenario analysis; prioritize development and drive organizational adoption.
• Lead select special projects: Manage time-bound, CEO-sponsored, cross-functional initiatives impacting the value-creation plan, establishing clear charters, success metrics, and handoff plans.

Desired Skills & Experience

• Minimum 10 years in Business/Enterprise operations including direct experience running an annual planning cycle end to end at a software company
• Proven track record of running a board cycle with private equity or growth equity investors.
• Experience holding real operating or business-operations leadership seats (not exclusively staff or advisory roles).
• Demonstrated ability to hold senior executives accountable to commitments while maintaining strong peer relationships.
• Experience eliminating unnecessary meetings, reports, and processes to streamline organizational efficiency.
• Hands-on experience personally redesigning operational workflows using AI tools.
• Strong financial literacy to partner effectively with Finance on resource envelopes and reallocation.

Bonus Points

• Early career background in management consulting or investment banking.
• Experience running an annual planning cycle end to end at a SaaS technology company with 200M-1B in ARR
• Experience with small-business customers, self-serve growth models, or healthcare technology.
• Previous experience acting as a product owner for internal tools.
• Annual base compensation range: $270,000—$315,000 USD.
• Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay. Determining pay considers factors including skills, experience, qualifications, geographic location, and other job-related factors.
• Benefits include medical, dental, vision, life, and disability insurance; a 401(k) plan with company match; flexible time off, wellbeing days, paid holidays, and summer Fridays; mental health resources; paid parental leave and backup care; tuition reimbursement; and employee resource groups.