Gatekeeper is the ONLY unified contract & third-party-risk management platform that protects compliance-centric organisations by delivering company-wide control to reduce risk and cost. Powered by our AI engine, LuminIQ, we embed risk checks, accelerate contracting, and surface savings in one platform—helping lean teams stay compliant, efficient, and audit-ready.

Gatekeeper has consistently achieved significant, profitable growth YoY, with our customer base including Ford, The Telegraph, Autotrader, SumUp, Crocs and Funding Circle.

Following private equity investment from Vista Equity Partners we are scaling rapidly and looking to build out our RevOps team.

Note: This is a fully remote position, open to applicants based in Ontario.

Role Overview

Gatekeeper is looking for a detail-oriented Revenue Operations Specialist to keep our go-to-market engine running cleanly day to day. You'll be the hands-on owner of our HubSpot instance and the operational backbone of our Deal Desk; making sure our CRM data is trustworthy, our workflows do what they should, and every quote and deal moves through approval quickly and correctly.

This is a foundational role on a growing RevOps function, reporting to the VP of Finance. It's ideal for someone early in their RevOps, Sales Ops, or CRM-admin career who wants broad exposure across systems, process, and the full quote-to-close motion - and who's ready to grow into more strategic work as the team scales.

Why this role

You'll sit at the centre of how Gatekeeper sells — touching systems, data, and process across the whole revenue team — with a clear path to grow into more senior RevOps work as the function matures.

What you'll do

HubSpot administration & CRM operations

Serve as day-to-day administrator of our HubSpot instance; managing users, permissions, properties, pipelines and deal stages.
Own CRM data hygiene: keep contact, company, and deal records accurate and complete, and run regular clean-up and de-duplication to keep reporting trustworthy.
Build, maintain, and troubleshoot workflows, automations, lead routing, and lead scoring.
Create and maintain dashboards and reports for Sales, customer-facing teams, and leadership (pipeline, conversion, deal velocity and activity).
Support CRM adoption, write short how-to documentation and help reps use the system correctly and consistently.
Help maintain integrations between HubSpot and the wider GTM tool stack, flagging sync issues before they affect data.

Deal desk & quote-to-contract support

Generate, validate, and process quotes, ensuring accuracy, completeness, and correct required fields to reduce downstream errors and rework.
Route deals through the approval workflow, applying pricing and discount policies consistently and escalating non-standard requests to the right approver.
Track deals in flight and keep quote cycle times moving, meeting agreed turnaround/SLA expectations.
Act as a first point of contact for reps' quoting and deal-process questions, providing guidance on standard terms and structure (with support for anything non-standard).
Coordinate with Sales, Finance and Legal to keep deals progressing cleanly from quote to closed-won.
Maintain deal-desk templates, approval matrices, and process documentation so the process stays consistent and auditable.

Process & continuous improvement

Spot recurring friction in CRM and deal workflows and suggest fixes.
Support ongoing RevOps initiatives; pipeline clean-ups, process rollouts, and improvements to how the team sells and reports.

Requirements

1–2 years in Revenue Operations, Sales Operations, Marketing Operations, CRM administration, or a Deal Desk/sales-support role (recent graduates with relevant internship or project experience are also encouraged to apply.)

Hands-on experience with HubSpot (or a comparable CRM such as Salesforce), including building or troubleshooting workflows and reports.
Solid grasp of CRM data models; objects, properties, and relationships, with a genuine passion for data accuracy.
Strong attention to detail and comfort working with quotes, numbers, and structured processes.
Clear written and verbal communication, and the ability to work collaboratively across multiple areas of the business.
Well-organized, able to manage multiple deals and requests in a fast-moving environment.
Comfortable with spreadsheets, documentation and basic reporting.

Nice to have

HubSpot certification(s) (e.g., Revenue Operations, Sales Hub, Reporting).
Exposure to a Deal Desk, quoting/CPQ tooling, or approval-workflow processes.
Familiarity with basic pricing, discounting, or contract terms and how they affect a deal.
Experience with revenue-intelligence or reporting tools (e.g., Gong, Clari, Looker, Tableau).
Understanding of B2B sales processes and the lead-to-cash lifecycle.
Bachelor's degree in Business, Finance, Marketing, or a related field (or equivalent practical experience).

Benefits

100% remote working: no offices and no commute
Generous paid vacation allowance
Comprehensive benefits package including:
- Private Medical & Dental cover
- GRSP Matching
- Employee Assistance Program
Learning & Development opportunities for lifelong learners
Technology: we provide everything you need to do your best work
Gatekeeper for Good: Match funding to support non-profit organisations in your local community
Gatekeeper retreats

We live by our company vision and values. If these ring true and if you’re a customer-focused professional passionate about growing and retaining high-value accounts, we’d love to hear from you!

Gatekeeper offers a diverse and multicultural working environment, currently spanning 15 countries. We respect each other’s differences and welcome candidates from all backgrounds.

Apply now to join Gatekeeper in our exciting journey of growth and innovation. Please note, this role is likely to involve some national and international travel.

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Revenue Operations Specialist