VP Revenue and Customer

Whooster, Inc. is seeking a Vice President of Revenue & Customer Growth (VP Revenue) to lead the next stage of growth across our two complementary businesses:
Whooster, our established investigative data business, and OWL Intelligence Platform, our newer SaaS intelligence and operational platform.

The VP Revenue will be responsible for transforming revenue execution, improving sales productivity, establishing operating discipline, and creating a scalable growth model capable of supporting the company's next phase of expansion.

The two businesses present different but complementary growth opportunities.

Whooster has an established recurring customer base and long-standing relationships across law enforcement, government, insurance, and commercial markets. Our customers include major federal, state, and local government organizations.

Whooster has an established customer base, active sales organization, recurring revenue foundation, and meaningful existing pipeline. The opportunity is not to build a revenue function from zero, but to improve how effectively the organization converts market activity and pipeline into predictable new revenue while expanding the value of existing customer relationships.

OWL is in an earlier startup and growth phase. The platform has already secured significant customers and developed meaningful opportunities in the market. The next stage requires stronger pipeline development and qualification, disciplined opportunity management, improved conversion, and a repeatable go-to-market strategy capable of scaling.

The VP Revenue will bring these opportunities together into predictable, diversified, and repeatable growth.

This is broader than a traditional VP of Sales position.

The VP Revenue & Customer Growth will have operational leadership responsibility for revenue execution across Whooster and OWL, including new-business sales, Sales Development, Customer Account Management, renewals and retention, account expansion, cross-selling, VAR and channel development, pipeline management, forecasting, and revenue operations.

The VP will partner with executive leadership and Finance to translate company growth objectives into executable revenue plans, including sales targets, capacity requirements, pipeline goals, account strategies, and operating priorities.

The VP will establish the processes, operating cadence, metrics, accountability structure, and sales discipline required to improve revenue performance and support future growth.

• Translate company revenue objectives into actionable sales goals, quotas, ownership, accountability, and performance expectations across the sales and customer-growth organization.
• Partner with executive leadership and Finance to develop revenue forecasts, capacity plans, sales coverage models, and go-to-market strategies aligned with company growth objectives.
• Increase core new-business production across existing and emerging markets.
• Improve conversion throughout the revenue funnel, from lead generation and qualification through opportunity management, proposal, close, and customer expansion.
• Establish and continuously improve a consistent sales methodology, qualification framework, opportunity review process, and sales operating cadence.
• Build qualified pipeline and improve forecasting accuracy and revenue predictability.
• Develop account-based sales strategies for high-value customers and prospects.
• Partner with Marketing on account-based marketing programs, target accounts, campaigns, and market development.
• Develop systematic Whooster-to-OWL and OWL-to-Whooster cross-selling opportunities.
• Protect and grow the recurring customer base through disciplined renewals, retention, customer success alignment, expansion selling, and additional customer opportunities.
• Build the VAR and channel program into a measurable source of qualified pipeline and revenue.
• Identify and develop new industry verticals and market opportunities.

Strong candidates will typically bring:

• 10+ years of progressive B2B sales and revenue experience with meaningful leadership responsibility.
• Experience in B2B SaaS, enterprise technology, data and information services, Gov Tech, public-sector technology, security, risk, insurance technology, or another relevant recurring-revenue business.
• Demonstrated accountability for meaningful annual revenue, ARR, or bookings targets.
• Experience building or materially improving a sales and revenue organization during a period of…