Revenue Operations Specialist

About Gatekeeper

Gatekeeper is a unique unified platform specializing in contract and third-party risk management aimed at compliance-centered organizations. It features Power AI engine LuminIQ that facilitates risk checks, accelerates contracting processes, and identifies savings across company procedures. This allows organizations to maintain compliance, enhance efficiency, and be audit-ready. Some of Gatekeeper's prominent clients include Ford, The Telegraph, Autotrader, SumUp, Crocs, and Funding Circle. Following private equity investment by Vista Equity Partners, Gatekeeper is rapidly expanding its Revenue Operations team.

Position Overview

This fully remote role is open specifically for applicants based in Ontario. The Revenue Operations Specialist will play a critical role in managing and optimizing Gatekeeper's go-to-market systems. As the day-to-day HubSpot administrator and Deal Desk operator, you will ensure reliability of CRM data, proper function of workflows, and smooth movement of quotes and deals through necessary approvals.

Key Responsibilities

• Administer HubSpot CRM by managing users, permissions, data properties, sales pipelines, and deal stages.
• Maintain CRM data cleanliness, regularly perform deduplication, and ensure data accuracy for dependable reporting.
• Develop, maintain, and troubleshoot workflows, automations, lead routing, and lead scoring mechanisms.
• Create and update dashboards and reports for sales teams and leadership highlighting pipeline health, conversion rates, deal velocity, and activity.
• Promote CRM adoption by creating concise user documentation and guiding sales representatives on proper system use.
• Oversee integrations between HubSpot and other GTM tools, identifying and resolving synchronization issues proactively.
• Generate, validate, and manage quotes, ensuring correctness and completeness to minimize errors and rework.
• Manage deal approval workflow, enforce pricing and discount policies consistently, and escalate exceptions appropriately.
• Monitor active deals to ensure timely quote cycle completion in line with SLAs.
• Serve as first contact for sales teams regarding quoting and deal processes, offering guidance on standard terms and structures, and collaborating with Finance and Legal on smooth quote-to-close transitions.
• Maintain and update deal desk templates, approval matrices, and documentation to preserve process consistency and audit readiness.
• Identify repetitive bottlenecks in CRM and deal workflows and propose improvements.
• Support broader RevOps initiatives such as pipeline clean-ups and process enhancements that improve sales efficiency and reporting accuracy.

Required Qualifications

• 1 to 2 years of professional experience in Revenue Operations, Sales Operations, Marketing Operations, CRM administration, or Deal Desk/sales support roles. Candidates with relevant internships or project experience are encouraged.
• Proficient hands-on knowledge of HubSpot or similar CRM platforms, including workflow and report configuration and troubleshooting.
• Strong understanding of CRM data models covering objects, properties, and relationships with a strong focus on data integrity.
• Exceptional attention to detail with comfort handling quotes, numerical data, and structured processes.
• Clear and effective communication skills with an ability to collaborate across departments.
• Strong organizational skills capable of simultaneously managing multiple deals in a dynamic environment.
• Comfortable working with spreadsheets, documentation, and fundamental reporting tasks.

Desirable Skills and Experience

• HubSpot certifications (e.g., Revenue Operations, Sales Hub, Reporting).
• Exposure to Deal Desk functions, CPQ or quoting software, and approval workflows.
• Understanding of basic pricing, discounting practices, and contract terms affecting deals.
• Experience with revenue analytics or reporting tools such as Gong, Clari, Looker, or Tableau.
• Familiarity with B2B sales cycles and lead-to-cash processes.
• Bachelor’s degree in Business, Finance, Marketing, or related disciplines, or equivalent experience.

Benefits

• Fully remote work with no office commute.
• Generous paid vacation time.
• Comprehensive benefits including private medical and dental coverage.
• Group Registered Savings Plan matching contributions.
• Employee assistance and wellness programs.
• Opportunities for continuous learning and professional development.
• Provision of necessary technology to perform at your best.
• Community engagement through matched funding for local nonprofits under the Gatekeeper for Good initiative.
• Company retreats for team building and collaboration.

Additional Information

Gatekeeper fosters a diverse and inclusive culture and operates across 15 countries. Applicants from all backgrounds are welcomed and respected. The role may require some national and international travel. Candidates driven by customer focus and keen to develop high-value accounts will find this role rewarding and aligned with the company vision and values.