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Customer Success (Onboarding)

HeyMilo AI

HeyMilo AI

Sales & Business Development, Customer Service
Toronto, ON, Canada
Posted on Feb 14, 2026
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. As we bring on more customers across staffing, BPO, and enterprise, we need someone who can own the onboarding experience from day one.

About The Role

This role sits at the intersection of solutions engineering, recruitment consulting, and customer onboarding. You'll be the person who takes a new customer from signed contract to fully live, translating their hiring workflows, business rules, and operational needs into a working HeyMilo configuration.

This isn't a hand-off-and-hope kind of onboarding role. You'll need to deeply understand how recruiting organizations operate, how they use their ATS, and how to map their processes into our platform. You're part consultant, part technical implementer, and part trusted advisor. If you've spent time in or around the recruiting and staffing industry and have a knack for turning messy business requirements into clean, scalable solutions, this is your kind of role.

What You Will Do

  • Own the end-to-end onboarding journey for new customers, from kickoff through go-live and early adoption.
  • Conduct discovery sessions with recruiting leaders, operations teams, and hiring managers to understand their workflows, candidate pipelines, and business goals.
  • Translate business requirements into platform configurations, including interview workflows, scoring criteria, candidate routing, and ATS integration setup.
  • Manage ATS integrations during onboarding (Bullhorn, Avionté, Greenhouse, Lever, Workday, and others), ensuring data flows correctly between systems.
  • Build onboarding plans tailored to each customer's complexity, team size, and timeline.
  • Train customer teams on how to use HeyMilo effectively, adapting your approach based on their technical comfort and organizational structure.
  • Identify risks and blockers early in the onboarding process and resolve them before they delay go-live.
  • Partner with Customer Success to ensure a smooth handoff once the customer is live and adopted.
  • Feed product insights back to Engineering and Product based on what you learn during implementation.

Who You Are

  • You have 5+ years of experience in customer onboarding, solutions engineering, implementation consulting, or a similar role at a software company, ideally at an early-stage company that scaled through Series A, B, or C.
  • You have real experience in the recruiting or staffing industry. You understand how recruiting teams work, how candidate pipelines flow, and how ATS platforms fit into daily operations.
  • You're confident working with applicant tracking systems (Bullhorn, Avionté, Greenhouse, Lever, Workday, or similar) and can speak the language of recruiters and TA leaders.
  • You can take a complex, sometimes ambiguous set of business requirements and turn them into a clear implementation plan.
  • You're a strong communicator who can run a discovery call with a VP of Talent Acquisition and a technical integration session in the same day.
  • You're highly organized and can manage multiple customer onboardings in parallel without dropping the ball.
  • You take ownership. When something isn't working, you fix it or find someone who can.
  • You've worked in fast-paced environments and are comfortable with ambiguity, shifting priorities, and building processes that don't exist yet.

Nice to Have

  • Experience in recruitment consulting or at a staffing agency.
  • Familiarity with integration platforms like Kombo or Merge.
  • Background in solutions engineering or pre-sales technical consulting.

Why Join HeyMilo

  • Own a critical part of the customer journey at a company that's growing fast and landing major accounts.
  • Use your recruiting industry expertise in a way that directly shapes how customers experience our product.
  • Work closely with Product, Engineering, and Customer Success, with real influence over how we build and deliver.
  • Grow your career in a high-trust environment where ownership and results matter more than titles.