People and Operations Manager

Highbeam•Toronto, ON

4d•Onsite

About The Position

Highbeam is building the future of business banking and cash management. Our platform combines AI agents, automated financial workflows, and integrated financial products that save brands time and money. Customers have generated billions in sales and include well-known brands such as Cuts, Tushy, NYON, Sabah, Still Here, Alice Mushrooms, Original Grain, birddogs, and more. Our team includes alumni of Shopify, Square, Toast, Rippling, and McKinsey. We’ve raised $42M in equity from Acrew, FirstMark, Mayfield, and Two Sigma Ventures. We’re hiring a People and Operations Manager to take ownership of the internal systems that run Highbeam and level them up as we scale. This is a hands-on role: you’ll run the day-to-day across people operations, recruiting coordination, payroll, and compliance, refining the processes and controls we already have in place and bringing more rigor to them as the team grows. You’ll help sharpen the policies that govern how we run by enforcing and embedding them into our intel AI agents, flag exceptions, and surface issues before they hit the team. This role is based in our Toronto office.

Requirements

3 - 5 years in people operations, HR, business operations, or a related cross-functional role, ideally at a startup or high-growth company
Experience running multi-jurisdiction payroll (US and Canada for us)
Comfortable working with employment lawyers, payroll tools, and ATS tools (Ashby a plus)
High attention to detail and discretion with sensitive information; pragmatic about when to keep things simple
Self-directed; you can identify what needs to get done without being told
Excellent communication skills, especially around sensitive topics like compensation and compliance
BA or higher, preferably in Finance, Business, Accounting, or a related field

Nice To Haves

Experience supporting H-1B or other immigration processes is a plus
Familiarity with Canadian employment law and ROE filings is a bonus
Interest in using AI tools (Claude, ChatGPT, or similar) to encode policies, build agentic workflows, and automate operational work is a plus
You love working in-person with a high-performing team
You enjoy working in an idea-meritocratic, low-ego environment
You are proactive and self-directed, and you excel in ambiguous, fast moving environments
You care about delivering a polished customer experience
Bonus: You have experience working in fintech, AI or early-stage startups

Responsibilities

Run payroll, contractor payments, and bonus cycles across the US and Canada, sharpening the cycles we already operate
Own employee onboarding end-to-end: offer letters, I-9s, payroll setup, and option grant coordination with outside counsel
Manage employee lifecycle transitions (onboarding, role changes, offboarding) with care and professionalism
Administer 401(k), parental leave, and other benefits programs, refining enrollment and rollover workflows as we grow
Review and process employee expenses in line with company policy, tightening controls where they’re loose
Maintain and iterate on HR policies and employment contracts as the team scales
Stay ahead of state, federal, and tax compliance (multi-state payroll, business registrations, insurance), modernizing the controls that protect the company
Own the candidate experience from first touch to offer, ensuring every interaction reflects the Highbeam brand
Own the ATS: maintain job postings, manage candidate pipelines with hiring managers, and keep hiring moving efficiently
Coordinate recruiting logistics including onsite schedules, candidate communications, and follow-up with external recruiters
Manage agency relationships, including contracts and payments
Source candidates directly, building out our pipeline for key roles