Compliance Risk Specialist (USA-Focused)

- Location: Remote, Canada
- Hours: 8:30 am - 5:00 pm EST
- Salary: $75,000 – $85,000 / year CAD
- Employment Type: Permanent Full-Time

Overview

The Risk Specialist is the operational engine of Raise's Risk & Compliance function. This role carries the process-driven execution of Raise's insurance and privacy compliance programs — underwriting data assembly, loss run analysis, evidence collection, questionnaire preparation, records maintenance, and audit remediation — plus first-line intake for cross-functional compliance questions.

The role exists so that Raise's compliance obligations run on time, every time, and so that strategic capacity within the function is freed to focus on broker negotiation, leadership, Data Protection Officer accountability, and expansion into new jurisdictions. The Risk Specialist owns defined processes outright; matters requiring judgment beyond documented guidance, regulator correspondence, or contractual commitment escalate to the Senior Compliance Officer & DPO. The role requires the ability to be flexible and pivot priorities quickly.

As part of our hiring process, the first step will include an interview conducted by an AI interviewer. This allows us to efficiently and fairly assess all applicants using consistent, unbiased questions.

Please note that this role has been cross-posted as we are considering candidates from either Canada or the USA. There is one role available.

Key Accountabilities

1. Insurance Program Operations (core of the role)

- Gather, organize, and quality-check underwriting data ahead of each of the three annual renewal cycles (US GL, US WC Captive/ISL, CAN GL) so renewal negotiations begin with complete submissions.
- Collect quarterly loss run reports and prepare first-pass summaries and trend flags feeding the ISL Captive program review.
- Conduct routine insurance viability checks for new clients and roles against documented criteria.
- Review escalated WC classification matters, maintain classification documentation and precedent records, and hold regular code-usage check-ins with the Coordinator.
- Review WC code and premium audit findings and remediate them, taking items back to the carrier.

2. Cybersecurity & Privacy Operations

- Collect, upload,



and organize control evidence in Vanta; monitor control status and flag drift or gaps before they become audit findings; maintain evidence, documents, and policies year-round.
- Prepare first drafts of client security and privacy questionnaires from the approved answer library, coordinate SME input, and manage the response pipeline to agreed turnaround times (11 questionnaires last year, trending up).
- Maintain records of processing activities and execute routine data transfer and cybersecurity policy documentation updates.

3. Compliance Programs & Advisory Support

- Act as first point of intake for ad hoc compliance questions from internal stakeholders: resolve routine matters against documented policy and guidance, route novel or high-risk questions with a complete situation summary.
- Assemble engagement details and complete the initial data-gathering stage of new client and vendor risk assessments.
- Handle routine policy interpretation per documented guidance.

4. Meetings, Research & Development

- Attend the implementation/roll-out cadence and recurring team and operational meetings alongside the Officer to hold operational context, capture action items, and carry follow-through work.
- Dedicated time for researching regulatory and jurisdictional requirements as they emerge, and working remediation items — audit findings, control gaps, and escalated fixes — through to closure.

What You Bring

The focus is primarily on the disposition of the individual — this role runs dozens of concurrent regulatory clocks and touches every part of the business:

- Exceptional organizational skills, self-discipline, and deadline/calendar discipline.
- Strong interpersonal, communication, and collaboration skills.
- Ability to take initiative and a self-directed working style — you thrive with clear ownership, ask for context rather than instructions, and are energized by a self-managed environment.
- Demonstrated competence in the tasks allocated to this role.

Experience





- 3–4 years of hands-on experience in US insurance operations — this is the primary experience profile for this role. Direct exposure to commercial lines (General Liability and Workers' Compensation especially), renewal cycles, underwriting data preparation, loss runs, WC classification codes, and carrier or broker interaction. Experience with captive insurance programs is a distinct asset.
- A broader risk foundation is the overarching benefit we're looking for on top of that insurance core: comfort thinking in terms of exposure, likelihood, and mitigation — the lens that ties the insurance, audit, and compliance sides of this role together.
- Exposure to cybersecurity or privacy compliance operations (SOC 2 evidence, security questionnaires, GDPR/PDPA awareness) is a growth dimension, not a prerequisite — a candidate with insurance and risk strength today can grow into the cybersecurity elements of the role as it matures.
- Contingent staffing or workforce solutions industry experience is a solid asset.
- Discretion with confidential candidate, employee, and client data.

About Raise

Raise is an established hiring firm with over 65 years of experience. We believe strongly in making the world a better place through work, which is why we’re a certified B Corporation and donate 10% of our profits to charity.

We strive to build teams that reflect the diversity of the communities we work in. We encourage all qualified applicants to apply, including people from traditionally underrepresented groups such as women, visible minorities, Indigenous peoples, people identifying as LGBTQ2SI, veterans, and people with visible/nonvisible disabilities.

We have a dedicated webpage for accommodations where you can learn more about what we offer, and request accommodation: https://raise.jobs/accommodations/.

In order to submit candidates for roles, our clients will sometimes require personal information to confirm the identity of applicants and their legal status to work. Raise will never ask you for personal or banking information unless you have been selected for a job. If you are ever unsure about the legitimacy of this or another job posting by Raise (or have any other questions), please contact us at +1 (phone hidden) or [email protected].

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📌 Compliance Risk Specialist (USA-Focused) (Canada)
🏢 Raise
📍 Canada