Temporary Pilot Single Engine Jobs in Illinois (NOW HIRING)

The Director, Revenue Operations is a senior player/coach leader responsible for Sales Operations, the lead-to-opportunity motion, and the RFx function at Origami Risk. Reporting to the VP of Revenue Operations, this role serves as one of the VP's primary operational deputies and is accountable for execution consistency across the revenue organization.

Core responsibilities include owning forecasting cadences, pipeline health, and inspection rigor, as well as driving alignment across Finance, Marketing Ops, Business Development, Sales, and Account Management leadership. The Director leads a team of managers and individual contributors (ICs), spanning Sales Ops and RFx, and is directly responsible for advancing the early-funnel transformation initiative.

This role is intentionally hands-on. The Director is expected to contribute directly to lead-to-opportunity process design, RFx optimization, and tooling evolution (including AI-assisted capabilities) while simultaneously building team capability and accountability. Success requires sound judgment on where to engage directly versus delegate, strong prioritization in a lean environment, and the ability to shape the function as the business evolves.

Starting base pay for this role is between $160,000 and $185,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The base pay range is subject to change and may be modified in the future. This role will be eligible for a bonus as well as competitive medical, dental, and vision benefits, wellness reimbursement, life insurance, and a 401(k) with company match. We offer vacation and sick leave benefits (under a flexible time off policy in most states).

Team Leadership & Development

• Manages and develops a team at both the manager and IC levels.
• Sets clear expectations, provides regular performance feedback, and partners with team members to identify development opportunities and support growth aligned with individual career goals and business priorities.
• Operates as a genuine player/coach, role-modeling hands-on execution while progressively building the team’s capacity to operate independently.
• Partners with the VP of Revenue Operations on team operating cadences, sprint planning, and prioritization to ensure the team is focused on the highest-leverage work.
• Builds a culture of accountability, continuous improvement, and cross-functional collaboration.

 

Lead-to-Opportunity Engine & RFx Ownership

• Serves as the senior owner of the lead-to-opportunity motion, providing strategic direction, removing blockers, and directly contributing to process design, analytics, and AI modernization efforts alongside Marketing Ops.
• Partners closely with the RFx Manager to align the Request for Proposal/Request for Information (RFP/RFI) process with the broader lead-to-opportunity framework, treating RFx as a critical conversion stage, not a siloed function.
• Leads the quarterly RFP business review, synthesizing win rates, cycle times, resource utilization, and process improvement opportunities for the VP and Chief Revenue Officer (CRO).
• Drives AI-assisted improvements across the early funnel in partnership with Marketing Ops by evaluating, piloting, and scaling tools that improve lead routing, activity capture, and RFx response quality.
• Maintains direct relationships with Business Development Leadership and Marketing Ops to ensure the early funnel is operating with clear Service Level Agreements (SLAs), shared definitions, and aligned attribution standards.
• Owns executive-level visibility into early-funnel performance, ensuring the VP and CRO have timely, accurate, and actionable reporting on lead conversion, pipeline sourcing, and RFx outcomes.

 

Forecasting, Pipeline Management & Revenue Cadences

• Leads the CRO’s weekly forecasting cadence and monthly pipeline council, owning the agenda, materials, and narrative that drive alignment on pipeline health and bookings outlook.
• Develops monthly forecasting analysis to validate leadership calls, surface risks and upside, and inform both the VP and CRO forecasts with a data-driven perspective.
• Standardizes forecasting and pipeline management processes across the RevOps team, establishing governance, documentation, and operating norms that create consistency and reduce dependency on any single individual.
• Partners with Sales Ops on the VP-level forecasting cadence and pipeline council to ensure seamless data preparation, coverage analysis, and follow-through.
• Owns the weekly pipeline roll-up for CRO and VP consumption, including bookings pacing, pipeline coverage, and conversion trend analysis.

 

GTM Operations & Process Excellence

• Partners with Finance to collaborate on annual territory and bonus plan modeling for the revenue teams, translating go-to-market strategy into rep-level plans that are grounded in capacity, coverage, and performance data.
• Works closely with the RevOps Program Leader and the Go-To-Market (GTM) technology team to prioritize and ensure the broader toolset (BI, sales engagement, revenue intelligence) supports clean data flow and seller productivity.
• Drives broad RevOps AI modernization in partnership with the RevOps Program Leader, identifying automation opportunities.
• Defines and enforces GTM-related KPIs at the VP/Director/Manager level, establishing annual reporting standards and ensuring consistent measurement across the revenue organization.
• Supports the VP on strategic initiatives, annual planning, and org design decisions, serving as a thought partner and operational executor on high-priority projects.

 

Cross-Functional Alignment & Stakeholder Management

• Serves as the primary RevOps point of contact for Marketing Ops, Business Development & Sales Leadership, Sales Enablement, Deal Desk, and GTM Apps, driving alignment on shared processes, data standards, and operating cadences.
• Partners with the Marketing Ops leader on funnel definitions and Marketing Qualified Lead (MQL) criteria to ensure a consistent and reliable view from first touch through closed won.
• Collaborates with Enablement to ensure that process and system changes are accompanied by effective change management, training, reinforcement, and adoption tracking that drives behavioral change in the field.
• Maintains working relationships with Customer Success leadership on retention metrics, handoff quality, and renewal-adjacent data that inform pipeline health and forecasting accuracy.
• Builds and maintains strong relationships with Sales leadership, serving as a trusted operational advisor on deal execution, pipeline strategy, and process improvement.
• Represents RevOps in cross-functional planning forums, executive reviews, and strategic initiative workstreams on behalf of the VP of Revenue Operations.

• Bachelor’s degree in business, Finance, or a related field; MBA or equivalent experience a plus
• 8+ years of progressive experience in Revenue Operations, Sales Operations, or a related GTM function within a B2B SaaS or technology company.
• 3+ years of people management experience, including managing managers or senior individual contributors; proven ability to develop talent in a lean, high-accountability environment.
• Demonstrated player/coach operating style, comfortable setting strategic direction while directly owning high-visibility deliverables.
• Hands-on experience owning or closely partnering on a lead-to-opportunity function, including early-funnel process design, conversion analytics, and Business Development/Marketing alignment.
• Familiarity with RFx processes and how they connect to pipeline generation and revenue conversion; prior experience managing or partnering with a proposal/RFP function is a strong plus.
• Experience leading forecasting cadences and building the analytical infrastructure (models, dashboards, processes) that make forecasting reliable and actionable.
• Fluency in SaaS revenue metrics, pipeline coverage ratios, ACV, NRR/GRR, bookings pacing, and the ability to translate operational data into these measures for senior leadership and executive audiences.
• Fluency with AI-native tools and workflows applied to RevOps, activity capture, routing automation, or similar; a genuine curiosity about how AI can improve GTM execution.
• Strong Salesforce proficiency and familiarity with the broader revenue technology stack (LeanData, ZoomInfo, Clay, etc.), including BI tools (Tableau, Looker, or similar), sales engagement platforms (Gong), and revenue intelligence solutions; experience influencing CRM strategy, enhancement prioritization, and data governance.
• Excellent executive communication skills, able to synthesize complex operational data into clear narratives for senior leadership and executive audiences.
• Proven cross-functional influence skills; comfortable operating across Marketing, Sales, Finance, and Enablement without formal authority.
• Up to 25% travel required.

• Medical and Dental coverage available for employees, dependents, domestic partners, and spouses
• Paid Time Off – Flexible options plus 10 paid company holidays where available**
• All full-time positions are hybrid, with many eligible to be completely remote
• Fully Paid by Origami Risk – Vision insurance, Short & Long-Term Disability Insurance, and Basic Life Insurance
• Generous family leave options—including adoption and foster care placements
• Pre-Tax Savings Accounts – Flexible Spending Account, Health Savings Account, Commuter Benefits, Dependent Care Savings Account
• Retirement Savings – 401(k) with company match up to 4%
• Employee Assistance Program (EAP) – Confidential & Free support offered to colleagues facing personal or work-related complications
• Education Assistance Program – to help colleagues pursue industry/role-specific certifications
• Wellness Benefits – reimbursement program to invest in healthy habits as well as support better colleague productivity and stress management
• Additional coverages available – Pet Insurance, Critical Illness Insurance, and Voluntary Life & AD&D coverage

Origami Risk delivers single-platform SaaS solutions that help organizations best navigate the complexities of risk, insurance, compliance, and safety management.

Founded by industry veterans who recognized the need for risk management technology that was more configurable, intuitive, and scalable, Origami continues to add to its innovative product offerings for managing both insurable and uninsurable risk; facilitating compliance; improving safety; and helping insurers, MGAs, TPAs, and brokers provide enhanced services that drive results.

A singular focus on client success underlies Origami’s approach to developing, implementing, and supporting our award-winning software solutions. 

Origami Risk is proud to be an equal opportunity employer. We thrive and benefit from diversity and are committed to creating an inclusive and equitable environment for all employees. We do not discriminate against any individual based upon race, religion, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, color, sex, national origin, age, marital status, military or veteran status, disability, or any other characteristic protected by applicable law.

Caution: Be alert to recruiting scams. We have received reports of individuals impersonating Origami Risk recruiters to deceive candidates into disclosing personal information. These impostors use fake Origami Risk domain names and email addresses. Please double-check that any email address from an Origami Risk recruiter ends with origamirisk.com or talent.icims.com. And to confirm the legitimacy of any recruiting communication, feel free to email transparencycheck@origamirisk.com.