About HeyMilo
HeyMilo is one of the fastest-growing AI recruiting platforms in North America, backed by leading Silicon Valley investors and trusted by top staffing agencies, BPOs, and Fortune 100 companies.
Our AI agents automate candidate engagement, eliminate fraud, accelerate screening, and help hiring teams make better decisions, faster. We're scaling rapidly and looking for people who want to grow with us.
About the Role
We're hiring a Chief of Staff to work alongside our founding team in Toronto. This is a high-leverage role for someone who has been through the startup-to-scaleup journey before and knows what it takes to keep a fast-growing company running smoothly while everything around it is changing.
You'll sit at the intersection of strategy, operations, and execution. One day you might be preparing materials for an investor update, the next you're driving a cross-functional initiative or helping the CEO prioritize what matters most this quarter. You'll have visibility into every corner of the business and a direct hand in shaping how we scale.
Because we're a recruiting technology company, having a background in talent acquisition or experience working with applicant tracking systems will help you ramp faster and understand our customers on a deeper level.
What You Will Do
Act as a strategic partner to the CEO and founding team, helping prioritize initiatives and allocate resources as we scale.
Drive cross-functional projects from planning through execution, keeping teams aligned and accountable.
Prepare materials for board meetings, investor updates, QBRs, and leadership offsites.
Identify operational bottlenecks and build lightweight processes that help the company move faster without adding unnecessary overhead.
Serve as a connective layer between teams (Engineering, Customer Success, Sales, Product), making sure information flows and nothing gets lost.
Own special projects that don't fit neatly into one team but are critical to the business.
Help build and refine internal planning rhythms, goal-setting frameworks, and reporting cadences as we grow from startup to scaleup.
Support hiring, people operations, and culture-building efforts as the team expands.
Who You Are
You've worked as a Chief of Staff, Head of Operations, or in a similar strategic role at an early-stage company (Series A through C). You've seen what the startup-to-scaleup transition looks like and you know how to navigate it.
You're a generalist at heart. You can switch between a financial model, a product discussion, and a people problem in the same afternoon without breaking a sweat.
You're an exceptional communicator, both written and verbal. You can draft a board memo and run a team standup with equal confidence.
You're deeply organized and naturally create structure in ambiguous environments.
You have strong judgment and know when to escalate, when to decide, and when to let things play out.
You're comfortable in tools like Google Workspace, Slack, Notion, and Linear.
You're not precious about title or scope. You'll do whatever needs to be done.
Preferred
Background in recruiting, talent acquisition, or HR technology.
Experience working with applicant tracking systems (Bullhorn, Greenhouse, Lever, Workday, Avionté, or similar).
Experience at a venture-backed company that went through meaningful growth inflection points.
Why Join HeyMilo
Join during a defining growth phase and help shape how the company scales.
Work side by side with the founders, with direct exposure to strategy, customers, investors, and product.
Learn at an accelerated pace across every function of the business.
Be part of a team that values speed, ownership, and building something that matters.
Competitive salary, health benefits, meaningful equity, RRSP match