Revenue Operations Lead Jobs in Chicago, IL

Role Overview

The Vice President of Enterprise Revenue Operations is an executive leader accountable for the systems, insights, people, and processes that fuel every stage of the revenue engine. Sitting at the intersection of Sales, Marketing, and Customer Success, this role unites our go-to-market ecosystem and turns collaboration into consistent, predictable growth.

Reporting directly to the Chief Revenue Officer, the VP is a highly visible, enterprise-level leader who shapes how the company executes its growth strategy. You will own forecasting, pricing and deal desk, data governance, and go-to-market technology, and provide strategic direction to sales training and enablement. Your recommendations will guide executive-level decisions.

Key Responsibilities

Revenue Strategy & Planning

• Set the vision: Own a multi-year RevOps and enablement strategy aligned to company growth targets.
• Lead forecasting: Deliver accurate, actionable revenue models and forecasts for the CRO and executive team.
• Orchestrate planning: Partner with Finance, Sales, and Marketing to lead annual, quarterly, and monthly planning and resource allocation.
• Uncover growth: Use data and market insight to identify untapped revenue, and shape investment across channels, brands, and segments.
• Design for performance: Own scalable territory models, quota frameworks, and compensation plans that inspire high achievement.

Cross-Functional Alignment

• Be the connective tissue: Bridge Sales, Marketing, Customer Success, and Finance to remove silos and drive seamless execution.
• Lead with influence: Establish operating rhythms around pipeline health, funnel performance, and forecast accuracy.
• Partner strategically: Work with Product and Finance on go-to-market readiness and launch planning for new products and offerings.
• Champion the customer: Design processes that deliver consistent, effortless experience across the buyer journey.

Sales Training & Enablement

• Set the direction: Define the enablement vision and priorities, and hold the Sales Training leader accountable for onboarding, ongoing development, and certification programs for sellers, managers, and account teams.
• Align to the motion: Ensure training reflects company methodology, product, pricing, and competitive positioning across multiple brands and sales motions.
• Reinforce coaching: Partner with sales leaders to embed coaching frameworks and use Gong insights to reinforce winning behaviors.
• Measure impact: Tie enablement outcomes to ramp time, win rate, deal size, and retention, and retire what does not move results.

Pricing & Deal Desk

• Own pricing strategy: Set pricing, packaging, and discounting strategy across brands, segments, and sales motions in partnership with Product and Finance.
• Build the deal desk: Design and stand up a scalable deal desk, with clear intake, approval matrices, SLAs, and escalation paths for non-standard pricing, terms, and contracts.
• Protect margin and velocity: Balance deal speed against margin, discount discipline, and risk, and monitor discount levels, price realization, and win rates.
• Streamline quote-to-cash: Partner with Finance, Legal, and Sales to simplify quoting, approvals, and booking, supported by CPQ and CRM workflows.
• Guide decisions: Deliver pricing analytics and competitive pricing insights that inform list pricing, renewal uplifts, and promotions.

Process Optimization

• Streamline the system: Remove friction across all revenue workflows, from lead generation through renewal and expansion.
• Standardize and scale: Build consistent, repeatable processes that drive efficiency, predictability, and customer satisfaction.
• Control the levers: Own renewal strategy, churn analysis, and at-risk account workflows to maximize retention and lifetime value.
• Drive utilization: Increase event fill rates, reduce cancellations, and optimize revenue per scheduled day.

Analytics, Reporting & Data Governance

• Command the numbers: Own a unified analytics framework covering pipeline velocity, conversion, CAC, LTV, churn, and retention.
• Own the data: Govern CRM and revenue tool integrity with enterprise standards for data quality, security, and accuracy.
• Illuminate insights: Deliver dashboards that give leadership real-time visibility into performance against targets.
• Turn data into action: Monitor cancellations, event utilization, and booking velocity to diagnose issues and recommend solutions.

Technology Leadership

• Own the stack: Set strategy and ROI for revenue tools including Salesforce, Gong, CPQ, and reporting platforms.
• Build for adoption: Ensure tools are integrated, intuitive, and drive measurable impact across all go-to-market teams.
• Scale through automation: Lead AI and automation initiatives that improve forecasting precision and efficiency.
• Document the foundation: Maintain clear documentation of system configurations, workflows, and data architecture decisions.

Team Leadership & Development

• Lead through leaders: Build, mentor, and inspire a multi-disciplinary organization spanning Sales Operations, Sales Training & Enablement, and Pricing & Deal Desk, including directors and managers.
• Set the bar: Establish clear goals, KPIs, and growth paths that drive performance and development.
• Influence at the top: Present data-backed insights and recommendations to the CRO and executive team.
• Own the budget: Manage the function's headcount, budget, and vendor spend.
• Foster excellence: Cultivate a culture of transparency, continuous improvement, and data-driven decisions.

Required

• 12+ years of progressive experience in Revenue Operations, Sales Operations, or Marketing Operations in a B2B environment, including 5+ years leading managers or directors.
• Proven success building and scaling RevOps functions, including ownership of forecasting and reporting.
• Experience directing sales training or enablement programs.
• Ability to influence executive stakeholders and drive accountability across functions.
• Deep experience in SaaS/subscription models, with mastery of NRR, GRR, and churn dynamics.
• Experience managing complex, multi-brand portfolios and varying sales motions.
• Experience building pricing strategy and deal desk functions, including approval governance and discount management.
• Expert-level CRM proficiency (Salesforce preferred), including CPQ and quoting workflows.
• Advanced analytical and financial modeling skills, including multi-touch attribution.
• Demonstrated success leading cross-functional change without direct authority.
• Experience presenting strategic findings to senior executives or the C-suite.
• Exceptional written, verbal, and visual communication.

Preferred

• Background in training, events, or professional services with high-volume scheduling environments.
• Expertise with BI tools such as Tableau, Looker, or Power BI.
• Experience with revenue intelligence platforms (Gong, Clari) and enablement platforms.
• Familiarity with CPQ, subscription management, or event registration solutions.
• MBA or advanced degree in Business, Finance, or a related field.

The Impact You'll Have

This role goes far beyond operations. It is about engineering growth at scale. You will build the framework that equips sellers, sharpens pricing decisions, and lets teams execute predictably, pivot strategically, and outperform expectations. If you thrive on aligning people, data, and strategy to unlock potential, this is your opportunity to lead from the center of impact.

About Certus

At Certus, your work has a direct impact. We help enterprises build capable, compliant workforces, and we help individuals at every stage of their careers earn industry-recognized credentials and move forward. Our portfolio of respected brands and our modern technology platform give you the scale to make a true impact and the room to grow your own career while you do it.

Every year, nearly 4 million learners turn to Certus to earn the credentials that open doors: a food handler card, a safety certification, a license to work. Behind each one is a team building the content, simulations, and technology that make it possible. If you want work that matters, join us

This is a remote position with some travel required for team meetings. Anticipated OTE is between $275,000 - $325,000 plus the opportunity to participate in long-term incentives.