Senior Implementation Consultant | REMOTE (ONTARIO)

Gatekeeper | part of Cinergy Group; Toronto; Hybrid; CAD 100,000 - 125,000; Full time

Job summary

A Software Implementation Company is looking for a Senior Implementation Consultant in Toronto (remote) to drive enterprise implementations of their AI-driven platform. Candidates should have 5+ years in software implementations, preferably in SaaS, and experience in leading high-impact projects. The role offers generous vacation, a comprehensive benefits package, and a chance to work in a fully remote environment.

Benefits

100% remote working

Generous paid vacation allowance

Comprehensive benefits package

Learning & Development opportunities

Technology support for work

Match funding for non-profit support

Qualifications

• 5+ years’ experience in software implementation or Professional Services roles within SaaS.
• Demonstrable history of leading high-impact projects and improving client satisfaction metrics.
• Deep understanding of SaaS customer success models and value realisation.

Responsibilities

• Lead complex, enterprise-grade implementations end-to-end.
• Partner closely with Account Directors to ensure seamless delivery.
• Identify opportunities for expansion through usage patterns.

Skills

Software implementation

Data analysis

Workflow logic

Mentoring

Customer success

Tools

Power BI

SQL

Job description

Description

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 achieved consistent, profitable growth year-over-year, serving customers such as Ford, The Telegraph, Autotrader, SumUp, Crocs, and Funding Circle. Following investment from Vista Equity Partners, we’re expanding our global Professional Services function and we’re looking for a Senior Implementation Consultant to help shape the next generation of delivery excellence.

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

ROLE OVERVIEW

As a Senior Implementation Consultant, you will play a strategic and hands‑on role in delivering transformative customer implementations. You’ll act as both a trusted advisor to enterprise customers and a mentor to other consultants - driving measurable success, AI‑led optimisation, and continuous improvement across our delivery practice. This is not just about onboarding software. It’s about helping customers transform the way they manage compliance, risk, and supplier relationships, powered by Gatekeeper’s AI-first platform.

WHAT YOU’LL DO

Customer Delivery & Strategic Advisory

• Lead complex, enterprise‑grade implementations end-to-end - from discovery to configuration, rollout, and optimisation.
• Translate business processes into scalable, automated Gatekeeper workflows, embedding LuminIQ’s AI and analytics capabilities.
• Design measurable success criteria (TTFV, ROI, adoption rates, renewal risk) and report progress through data‑led insights.
• Partner closely with Account Directors and Technical Account Managers to ensure seamless delivery and post-go-live health.
• Facilitate solution design workshops and executive‑level reviews that align technical outcomes to strategic objectives.

AI, Automation & Data

• Create AI prompt frameworks and scalable automations that improve process efficiency and user experience.
• Analyse customer data, translating metrics into business value (ROI, savings, and utilisation).
• Support the continuous evolution of Gatekeeper’s AI capabilities through product feedback and pilot projects.

Commercial & Cross‑Functional Collaboration

• Identify opportunities for expansion (upsell/cross‑sell) by recognising patterns in usage, AI adoption, and business impact.
• Collaborate with Product to share customer insights and shape platform evolution.
• Act as a bridge between customer needs and Gatekeeper’s technical roadmap, influencing improvements that scale value.

Continuous Improvement & Innovation

• Regularly review and refine delivery methodologies to reduce implementation time, risk, and effort.
• Stay at the forefront of AI, SaaS delivery, and automation trends, continuously experimenting and sharing learning.

Requirements

• 5+ years’ experience in software implementation or Professional Services roles within SaaS, ideally in CLM, Procurement, or Risk Management technology.
• Demonstrable history of leading high-impact projects, delivering measurable value, and improving client satisfaction metrics.
• Proven track record of mentoring or leading peers, even in an informal capacity.
• Strong grounding in data analysis, workflow logic, and configuration management.
• Deep understanding of SaaS customer success models, value realisation, and ARR growth levers.
• Exposure to AI-enabled workflows or automation platforms preferred.

Nice to Have

• Experience with Vendor Management or Contract Lifecycle Management (CLM) platforms.
• Familiarity with BI tools (e.g., Power BI, Looker, Tableau) or SQL for reporting and analytics.
• Exposure to change management or enablement strategy within enterprise SaaS.

This role is ideal for someone who:

• Has a consulting mindset and can think both strategically and technically.
• Is commercially sharp, understanding both customer outcomes and company growth levers.
• Is energised by innovation, especially in AI, automation, and digital transformation.

What we offer

• 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