Vice President Operations & Enablement

Department:
Growth / Sales Operations

Reports To:

Chief Growth Officer

Location:

Hybrid/Remote (as applicable)

The Vice President, Growth Operations & Enablement is the senior leader responsible for building and running Skyline’s sales operations function, including forecasting, pipeline management, sales process, CRM, enablement, and analytics. This role gives the growth organization the processes, systems, and data it needs to hit revenue and margin targets as Skyline moves upmarket and shifts to a programmatic, asset-based model.

The VP leads Presale Operations, Proposal Management and CRM, along with the broader sales operations team, and serves as the primary liaison between Sales and Finance. This leader turns the growth strategy into a working operating rhythm: accurate forecasts, clean pipeline data, a consistent sales process across every level of the growth & sales career path, and incentive plans tied to realized margin and retention.

• Own the sales forecasting process, delivering accurate and timely forecasts of bookings, revenue, and margin.
• Define pipeline stages, entry and exit criteria, and hygiene standards so that reported pipeline reflects real, qualified opportunities.
• Monitor funnel health and conversion by stage, account tier, and seller; flag risks early and recommend corrective action.
• Partner with growth leadership on annual planning, quota setting, account and territory assignment, and performance tracking.

• Design and implement a standardized, company-wide sales process from first meeting through signed contract, including qualification criteria and deal review standards.
• Align the sales motion to the programmatic, asset-based model and the move upmarket to larger, multi-event exhibit programs.
• Build onboarding, training, and ongoing enablement programs for account executives at every level of the career path.
• Ensure adherence to process and best practices through deal reviews, pipeline inspections, and coaching support for sales managers.

• Own CRM (e.g., Dynamics) configuration, adoption, and data integrity to maximize productivity and compliance.
• Manage the sales technology stack, including integrations with marketing, finance, and proposal tools, and evaluate new tools against measurable productivity gains.
• Set data standards and ownership rules so that account, contact, opportunity, and pricing data is complete and reliable.

• Collaborate with FP&A to provide sales data, analytics, and business intelligence that inform growth strategy, account prioritization, and resource decisions.
• Build and maintain dashboards tracking KPIs, OKRs, win rate, APV, and margin.
• Ensure data accuracy and consistency across CRM, finance, and reporting tools, with one agreed source of truth for pipeline and bookings.
• Deliver executive-level and board-ready reporting on pipeline, forecast, and growth performance.

• Serve as the primary liaison between Sales and Finance, reconciling forecast, bookings, and actuals.
• Support incentive compensation design tied to realized margin and retention, and ensure plans are administered accurately and on time.
• Translate field feedback into concrete improvements to process, pricing, and systems.

• Lead the Director of Presale Operations, the Director of RFP Management, the CRM team and other sales operations staff.
• Recruit, develop, and retain a high-performing team; establish performance expectations, development plans, and succession strategies.
• Run the sales management cadence and operating reviews, including weekly pipeline reviews, monthly forecast calls, and quarterly business reviews.
• Ensure opportunity intake, Go/No-Go governance, RFP management, and sales operations work as one connected function, with clear handoffs from intake through close.

• Bachelor's degree in Business, Finance, Marketing, or a related field; MBA preferred.
• 12+ years of experience in sales operations, revenue operations, sales strategy, or related functions.
• 5+ years of leadership experience running sales or revenue operations teams, including managing managers.
• Experience in a B2B professional services, agency, experiential marketing, exhibit, or other project-based environment with complex, custom deals.
• Demonstrated success building forecasting, pipeline management, and CRM disciplines in a growing…