Talent.com
HeyMilo AI
Senior Account ExecutiveHeyMilo AI • Toronto, ON, Canada
Senior Account Executive

Senior Account Executive

HeyMilo AI • Toronto, ON, Canada
30+ days ago
Job type
  • Full-time
Job description

HeyMilo is redefining how companies hire with agentic AI—backed by leading Silicon Valley investors and trusted by top staffing agencies, global BPOs, and Fortune 100 enterprises. Our AI agents automate candidate engagement, eliminate fraud, accelerate screening, and enable hiring teams to make dramatically better decisions with unmatched speed and accuracy.

As demand accelerates across every segment of the recruiting industry, we are rapidly expanding our GTM organization. We’re hiring A-player Account Executives who are obsessed with winning, thrive in high-performance environments, and want to play a defining role in shaping a rocket-ship company. This role is for someone who takes pride in excellence, owns their outcomes end-to-end, and wants to close meaningful deals that reshape how the world hires.

What You Will Do

  • Own the full sales cycle—prospecting, discovery, demos, solutioning, negotiation, and closing.
  • Run complex 5- and 6-figure deals with multi-stakeholder buying groups across HR, TA, Operations, IT, Compliance, and Finance.
  • Sell a category-leading product by demonstrating how HeyMilo outperforms competitors in accuracy, speed, fraud detection, and real-world complexity.
  • Lead strategic conversations with executives across staffing agencies, BPOs, and mid-market to Fortune 100 corporates.
  • Diagnose workflows and hiring pain points to drive urgency and ROI-focused decision-making.
  • Collaborate cross-functionally with Product, Engineering, and Customer Success to ensure smooth handoffs and long-term customer success.
  • Execute with speed, precision, and ownership to help capture market share in a rapidly growing category.

Who You Are

  • A top-performing AE who consistently exceeds quota and holds themselves to elite standards.
  • A true full-cycle seller capable of independently running outbound, discovery, demo, solution design, negotiation, and close.
  • Experienced navigating complex 5- and 6-figure SaaS deals and presenting to senior leaders.
  • A clear, confident communicator who can simplify technical concepts and speak credibly to executives.
  • Highly competitive with a strong internal drive to win and outperform alternatives.
  • Thrives in a high-growth, fast-moving environment where urgency, ownership, and excellence are the baseline.
  • Have sold agentic AI capabilities to organizations previously
  • Curious, product-minded, and comfortable understanding integrations, data flows, and real-world hiring operations.
  • Customer-obsessed and committed to delivering outcomes—not just closing deals.

Why Join HeyMilo

  • Join a hyper-growth company transforming high-volume hiring across staffing, corporate recruiting, and BPOs.
  • Sell a product that consistently wins competitive evaluations and delivers clear, measurable ROI.
  • Work alongside a team of top performers who expect excellence and celebrate big wins.
  • Own high-impact deals that directly influence HeyMilo’s growth and market position.
  • Be part of a culture rooted in grit, speed, accountability, and results.
#J-18808-Ljbffr
Create a job alert for this search

Senior Account Executive • Toronto, ON, Canada

Similar jobs

Senior Account Executive

Borderless AIToronto, ON, CA
Full-time

We’re on a mission to become the world’s most customer‑obsessed HR platform.Headquartered in Toronto, Canada, Borderless AI is a global payroll solution that leverages generative AI to automate and... Show more

 • Promoted

Senior Enterprise Account Executive Heavily Involved in Sales Strategy

RootlyToronto, ON, CA
Full-time

Join as a Senior Enterprise Account Executive and influence growth in a pioneering software startup.Use your extensive sales experience to engage clients while refining our sales approach dynamical... Show more

 • Promoted

Senior Account Executive, Mid-Market - Canada

SquareToronto, ON, CA
Full-time

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square.After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, ... Show more

 • Promoted

Senior Account Executive

Sales Talent AgencyToronto, ON, CA
Full-time

Senior Account Executive (Leadership Track).Location: Remote across Canada (Ideally in EST).Our client provides AI-powered software solutions that help solar, renewable energy, and infrastructure o... Show more

 • Promoted

Senior Account Executive

SageToronto, ON, CA
Full-time

You've prospected new customers.Now what? You will have a front row seat to influencing the success of our company.Our software makes life easier for small to midsized business and you will be the ... Show more

 • Promoted

Senior Account Executive, Toronto

SAPToronto, ON, CA
Full-time

Account & Customer Relationship Management: Serve as the end-to-end account owner, managing sales of software licenses and cloud subscriptions and establishing a trusted relationship with the custo... Show more

 • Promoted

Senior Enterprise Account Executive

Jaide HealthToronto, ON, CA
Full-time

RouteThis is on a mission to revolutionize technical support.We build AI‑powered solutions that help Internet Service Providers and Smart Home companies solve connectivity and WiFi problems—before ... Show more

 • Promoted

Drive Revenue Growth as a Senior Enterprise Account Executive

DiagramToronto
Full-time

Become a pivotal force in driving revenue as an Enterprise Account Executive.Leverage your expertise in software sales to deliver tailored solutions that align with client needs in a dynamic consul... Show more

 • Promoted

Senior Account Executive

BALLY’S INTRALOT SAToronto, ON, CA
Full-time

Bally’s Intralot is a leading provider of lottery, iLottery, sports betting, and digital gaming solutions, serving regulated gaming organizations across the United States and international markets.... Show more

 • Promoted

Senior Account Executive & Business Development SaaS Growth

NCR VoyixToronto, ON, CA
Full-time

A leading global digital commerce provider is seeking an Account Executive for Business Development in Toronto, Ontario.This role requires managing and growing client relationships while driving bu... Show more

 • Promoted

Senior Account Executive in Sales Partnerships

DiabsolutToronto, ON, CA
Full-time

Join Diabsolut as a Senior Account Executive focused on sales partnerships.This remote position emphasizes strategic relationship building within our vendor ecosystem, especially with Salesforce an... Show more

 • Promoted

Senior Account Executive — Ecommerce Financing

ClearcoToronto, ON, CA
Full-time

A technology-driven financial service provider is seeking an experienced sales professional to drive growth within Ecommerce businesses.Key responsibilities include managing the sales cycle, nurtur... Show more

 • Promoted

Senior Account Executive, Omnichannel Media

EQ WorksToronto, ON, CA
Full-time

EQ Works is seeking a senior, consultative sales professional to drive strategic growth across brands and agencies through data-powered omnichannel media solutions.This role is ideal for someone wh... Show more

 • Promoted

Senior Enterprise Account Executive Role

jobr.proToronto, ON, CA
Full-time

Advance your career as a Senior Enterprise Account Executive at IonQ based in Toronto, Canada.This critical role focuses on building executive relationships and generating significant sales pipelin... Show more

 • Promoted

Senior Account Executive at Rootly

RootlyToronto, ON, CA
Full-time

Step into a pivotal role as a Senior Account Executive at Rootly, focusing on enterprise clients and high-value sales opportunities.Your contributions will shape the way we manage incidents.In this... Show more

 • Promoted

Senior Account Executive

Clutch CanadaToronto, ON, CA
Full-time

HeyMilo is redefining how companies hire with agentic AI—backed by leading Silicon Valley investors and trusted by top staffing agencies, global BPOs, and Fortune 100 enterprises.Our AI agents auto... Show more

 • Promoted

Senior Account Executive

Pilothouse DigitalToronto, ON, CA
Full-time

DTC is a fast-growing B2B media outlet reaching over 155,000 ecommerce marketers and brand founders.Since 2020, we’ve delivered actionable insights that inform, inspire, and entertain operators nav... Show more

 • Promoted

Senior Account Executive

InfoTrack CanadaToronto, ON, CA
Full-time

InfoTrack Canada is a fast‑growing legal technology company modernizing the infrastructure that connects law firms, lenders, title insurers, government registries and other ecosystem partners.Hunt ... Show more

 • Promoted

Senior Account Executive

HeyMilo AIToronto, ON, CA
Full-time

HeyMilo is redefining how companies hire with agentic AI—backed by leading Silicon Valley investors and trusted by top staffing agencies, global BPOs, and Fortune 100 enterprises.Our AI agents auto... Show more

 • Promoted

Senior Enterprise Account Executive, Canada Growth

ComputacenterToronto, ON, CA
Full-time

A leading independent technology partner is seeking an experienced Sales Account Manager to join their team in Toronto, Ontario.This role involves managing and growing Enterprise Class Customers, d... Show more