Software Engineer, AI Automation

About us

The company is the world's first Active Insurance provider designed to help prevent digital risk before it strikes. Founded in 2017, the company combines comprehensive insurance coverage and innovative cybersecurity tools to help businesses manage and mitigate potential cyberattacks.

Opportunities to make an impact with bold thinking are real—and happening daily at the company.

About the role

We are hiring a Software Engineer for the Automation team to use AI to solve and automate manual work across the company. This is a hands-on AI engineering role: authoring skills, wiring agents to our systems of record through MCP, building evals, and deploying agents that non-engineers depend on every day. You will not be starting from zero. We have early workflows live in production, more proofs of concept in the oven, and working hypotheses about how all of this should fit together. We want someone who will pressure test those hypotheses against their own experience and change our minds where we have it wrong. Deep, current, practical experience building with LLMs is the single most important qualification for this job.

The other half of the role is proximity to the business. Think of this as a Forward Deployed Engineer, pointed inward: your customers are other the company teams. You will work directly with the teams whose work we are automating, learn how they actually operate, and turn that into a playbook. Getting from that conversation to something an agent can run reliably is the core of the work. You will also work day to day with our data team to get at the data these agents depend on. This is an individual contributor role with no direct reports.

Responsibilities

• Author skills: Turn a team's process, judgment, and edge cases into reusable skills that agents can invoke. Write them so the next project can reuse them instead of rebuilding them.

• Build within our agent architecture: Wire agents to the systems of record through MCP servers, compose skills and tools into working workflows, and add new MCP surface area when a system we need is not covered yet.

• Build evals: Define what "correct" means with the business team before you build. Build the eval set, establish a baseline, and use it to make calls about what ships. Nothing goes live on vibes.

• Deploy and support agents: Take agents from prototype to production, including permissions, human-in-the-loop checkpoints, audit trails, and rollback. Tune from how they behave once real users are in front of them, and leave behind docs and an owner on the business team who can run it without you.

• Partner with the data team: Work with our data engineers on the access, models, and quality of the data your agents read and write. Bring them requirements early rather than working around them.

Skills and Qualifications

• AI application building (primary): Substantial hands-on experience shipping LLM-backed applications: prompting, tool use, agentic loops, and multi-step workflows. You know where these break and how to contain the damage when they do. You have shipped at least one agent that non-engineers depend on.

• Agent tooling: Practical experience with MCP, skill or tool authoring, and orchestrating agents against real systems of record.

• Evals: You have built eval sets and used them to make decisions, not just to make a slide look good.

• Coding agents: Fluent with agentic coding tools like Cursor. You use them to move faster inside codebases you did not write.

• Core development: Strong Python. Comfortable with SQL and working directly against production data models.

• Business fluency: You can sit with a non-technical operator, map their process, and translate it into requirements without a PM in the room.

• Comfort with ambiguity: Undocumented processes, half-broken internal tools, and unclear ownership are the normal starting conditions. You find the thread and pull it.

• Shipping discipline: Git, CI, containers, and enough operational instinct to deploy your own work and keep it healthy.

• Experience: At least 5+ years of hands-on software development experience. It's not the years, it's the miles.

Bonus Points

• Experience building or maintaining MCP servers.

• Prior solutions engineering, professional services, internal tools, or startup founding experience.

• Working knowledge of the systems we automate against: Linear, Jira, Zendesk, Salesforce, Snowflake.

• Insurance, fintech, or another regulated domain where being wrong has a compliance cost.

Compensation

As a remote-first organization, our compensation reflects the cost of labor across several Canadian geographic markets.

In Alberta, British Columbia & Ontario the base salary for this position ranges from $128,500/year up to $160,600/year.

For all other locations, the base salary for this position ranges from $115,600/year up to $144,540/year.

Consistent with applicable laws, an employee's pay within this range is based on a number of factors, which include but are not limited to relevant education, skills, job-related knowledge, qualifications, work experience, credentials, and/or geographic location. Your Recruiter can share more on the specific target salary range for your location during the interview process. The company reserves the right to modify this range as needed.

Vacancy Status: This posting is for an existing vacancy.

Use of AI:  We utilize AI-assisted tools to help us organize and review the high volume of applications we receive. However, our human recruiting team makes all final hiring decisions and interview selections, valuing personal connection over algorithms.

Application Updates: Consistent with our commitment to transparency, if you are interviewed for this role, we will provide a status update on your application within 45 days of your final interview.

Perks

• 100% medical, dental, and vision coverage

• Flexible PTO

• Annual home office stipend and WeWork access

• Mental & physical health wellness programs like Headspace, Lumino, and more!

• Competitive compensation and opportunity for advancement

Why the company?

Work at the company is centered on the joint mission to Protect the Unprotected. We have built a remote-first, highly inclusive culture that welcomes people from diverse backgrounds. We trust each other to take responsibility, share ownership of outcomes, and put in the work together to protect businesses from digital risk. The company’s exceptional growth stems from its ability to address real-world problems for organizations of all sizes while remaining true to our founding values of character, humility, responsibility, purpose, authenticity, and inclusion.

We’re always looking for collaborative, inquisitive individuals to join #OurCoalition.

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Anti-Discrimination Notice

The company is proud to be an Equal Opportunity employer. Our policy is to provide equal employment opportunities to all individuals, without discrimination or harassment on the basis of any characteristic protected by applicable laws in each country where we operate. This commitment includes, but is not limited to, ensuring equal treatment in recruitment, selection, training, promotion, transfer, compensation, and all other aspects of employment. The company does not tolerate discrimination or harassment of any kind, and we are dedicated to fostering an inclusive and supportive workplace.

Accommodations

The company is committed to providing reasonable accommodations to qualified individuals with disabilities, including applicants and employees, in accordance with applicable laws and regulations in each country where we operate. Our policy is to support equal opportunity in the hiring process by considering qualified applicants regardless of disability or other protected characteristics, unless providing accommodation would impose an undue hardship or disproportionate burden. If you require accommodation to complete an application, interview, pre-employment testing, or participate in the selection process, please contact us at [link for members] . We also consider all qualified applicants, including those with criminal histories, in line with applicable laws and regulations in each jurisdiction.

To all recruitment agencies: the company does not accept unsolicited agency resumes. Do not forward resumes to our email alias, employees, or other physical or virtual organization locations. The company is not responsible for any fees related to unsolicited resumes.