Senior Account Executive at HeyMilo | Toronto

At HeyMilo, we are revolutionizing the hiring process with our cutting-edge AI technology. Supported by top-tier investors from Silicon Valley and trusted by prominent staffing agencies, global BPOs, and Fortune 100 companies, our innovative AI agents streamline candidate engagement, mitigate fraud, expedite screening, and empower hiring teams to make superior decisions swiftly and accurately.As we experience rapid growth across the recruiting landscape, we are expanding our go-to-market (GTM) organization. We are on the lookout for high-caliber Account Executives who are driven by success, excel in competitive environments, and are eager to contribute to the evolution of a fast-paced, high-impact company. This opportunity is ideal for individuals who take pride in their achievements, own their results from start to finish, and aspire to close significant deals that redefine the hiring landscape.What You'll Be Doing:Manage the complete sales process, including prospecting, discovery, product demonstrations, solution design, negotiation, and closing deals.Handle complex 5- and 6-figure contracts involving multiple stakeholders across HR, Talent Acquisition, Operations, IT, Compliance, and Finance.Promote our market-leading product by showcasing how HeyMilo excels in accuracy, speed, fraud detection, and navigating real-world complexities.Engage in strategic discussions with executives from staffing agencies, BPOs, and mid-market to Fortune 100 companies.Analyze workflows and hiring challenges to instill urgency and drive ROI-focused decision-making.Collaborate with teams in Product, Engineering, and Customer Success to ensure seamless transitions and long-term client satisfaction.Execute with speed, precision, and accountability to help capture market share in a rapidly expanding sector.Who You Are:A high-achieving Account Executive who consistently surpasses quotas and adheres to elite performance standards.A proficient full-cycle sales professional capable of managing outbound efforts, discovery, demonstrations, solution design, negotiations, and closings independently.Experienced in navigating intricate 5- and 6-figure SaaS contracts and presenting to senior management.An articulate and confident communicator who can distill technical concepts and engage effectively with executives.Highly competitive with a strong internal drive to excel and outperform the competition.Thrives in a dynamic, fast-paced environment aimed at significant growth.

About HeyMiloHeyMilo is a rapidly expanding AI recruitment platform in North America, supported by top-tier Silicon Valley investors and relied upon by leading staffing agencies, BPOs, and Fortune 100 companies.Our innovative AI agents streamline candidate engagement, mitigate fraud, expedite screening processes, and empower hiring teams to make informed decisions swiftly. As we scale, we seek individuals who are eager to grow with us.About the RoleWe are on the lookout for a Chief of Staff to collaborate with our founding team in Toronto. This pivotal role is ideal for someone experienced in navigating the startup-to-scaleup journey, equipped with the insight necessary to maintain smooth operations in a fast-paced, evolving environment.You will be positioned at the crossroads of strategy, operations, and execution. Your responsibilities may include preparing materials for investor updates one day and spearheading cross-functional initiatives or assisting the CEO in prioritizing key objectives the next. You will gain visibility into every aspect of the business and play a crucial role in shaping our scaling strategy.Given our focus on recruitment technology, a background in talent acquisition or experience with applicant tracking systems will enable you to quickly acclimate and gain a deeper understanding of our clients' needs.

HeyMilo is a rapidly expanding AI recruiting platform, supported by prominent Silicon Valley investors and relied upon by premier staffing agencies, BPOs, and Fortune 100 companies. Our innovative AI agents streamline candidate engagement, reduce fraud, enhance screening processes, and empower hiring teams to make informed decisions with remarkable speed.Due to increasing demand, we are growing our Customer Success team. We seek top-tier Customer Success Managers who have a passion for driving customer success, excel at onboarding clients, and can effectively manage integrations with ATS and HR systems.Key ResponsibilitiesOversee end-to-end onboarding, ensuring clients go live promptly by configuring workflows, managing ATS integrations (Bullhorn, Avionté, Greenhouse, Workday, etc.), and fostering early adoption.Manage a diverse portfolio of clients, including staffing agencies, BPOs, and Fortune 100 enterprises, supporting them in activation, usage optimization, and ongoing success.Conduct Quarterly Business Reviews (QBRs), strategy sessions, and workflow assessments linked to measurable ROI.Develop strong relationships with talent acquisition leaders, HR executives, Recruiting Directors, and Operations stakeholders.Identify opportunities for expansion based on client usage patterns, volume, and business objectives.Monitor account health, usage trends, and integration efficiency; proactively address any challenges.Collaborate with Product and Engineering teams to communicate customer insights and influence product roadmap direction.Facilitate smooth transitions between Sales, Onboarding, and Success to ensure high adoption and retention rates.Desired QualificationsProven experience as a Customer Success Manager or in a client-facing role with a strong background in onboarding, adoption, and account growth for SaaS platforms.Proficient in navigating technical workflows, ATS/HRIS integrations, APIs, and troubleshooting setup challenges.Exceptional communicator capable of simplifying complex ideas and influencing senior stakeholders at staffing firms and Fortune 100 companies.Highly customer-focused, proactive, and dedicated to achieving outcomes—not just completing tasks.Thrives in a fast-paced, high-growth environment where urgency, accountability, and excellence are paramount.Familiarity with ATS/HRIS platforms such as Bullhorn, Avionté, Greenhouse, Workday, Lever, and Dayforce is a significant advantage.

About HeyMiloHeyMilo is at the forefront of developing AI interviewers that engage in genuine conversations with candidates. Our technology empowers companies to expedite their screening processes and enhance their hiring decisions through advanced conversational AI.As a dynamic and agile team, we collaborate closely with clients to tackle real-world challenges.The RoleWe are looking for a talented software engineer to join our special projects team.In this pivotal role, you will take ownership of solving ambiguous, real-life problems while delivering solutions swiftly. Your work will span product development and engineering, crafting end-to-end solutions that are actively utilized.Key ResponsibilitiesRapidly build and deploy full-stack solutionsPrototype innovative AI-driven features and workflowsTransform vague requirements into functional systemsIterate quickly based on user feedback and real-world usageMake practical trade-offs to maintain paceQualificationsProven experience in full-stack or backend development (Python, TypeScript, etc.)Familiarity with large language models (LLMs) and prompt engineeringExtensive user of AI coding tools (Cursor, Claude Code, Codex, etc.)Strong understanding of databases, APIs, and system designAbility to simplify complex problems into effective solutionsDemonstrated ownership, resourcefulness, and focus on executionComfortable working under pressure and meeting tight deadlinesPreferred QualificationsExperience with conversational AI or telephony systemsBackground in developing production AI systemsWhy Join Us?High degree of ownership and rapid iterationAddress genuine challenges faced by real usersSmall team with minimal bureaucracyWork on impactful projects that benefit our customers and productCompetitive salary, benefits, and RRSP matching

About HeyMiloAt HeyMilo, we are revolutionizing the hiring process with our advanced AI interviewers, designed to streamline and enhance recruitment through engaging conversational AI. We partner closely with businesses to seamlessly integrate AI into their hiring workflows.The RoleWe're seeking a talented deployed solutions engineer to engage in special projects that bridge engineering, product development, and customer requirements. In this role, you will take the lead in applying HeyMilo's solutions across diverse environments and guide projects from conception to execution.What You Will DoCollaborate with customers to grasp their workflows and requirementsDesign and create prototypes that address real-world challengesConvert business needs into actionable technical solutionsEngage with APIs, integration processes, and system architectureWork alongside engineering teams to transform solutions into deployable systemsWhat We Are Looking ForA solid technical foundation with coding capabilitiesExperience in working with large language models (LLMs) and prompt engineeringProficient user of AI tools for rapid development (e.g., Cursor, Claude, Codex)Excellent communication and problem-solving skillsAbility to navigate ambiguity and act swiftlyComfortable functioning under pressure and meeting tight deadlinesBonus Points ForExperience with enterprise-level deployments or integrationsFamiliarity with telephony or voice AI systemsWhy Join Us?Tackle high-impact challenges across various customer projects and productsGain high visibility and ownership over projectsThrive in a fast-paced, execution-focused environmentEnjoy competitive compensation, benefits, and RRSP matching

As an Account Executive at mergeapiintegrationsandbox, you will play a pivotal role in driving our growth and success. You will be responsible for managing client relationships, identifying new business opportunities, and ensuring high levels of customer satisfaction.Your ability to understand client needs and deliver tailored solutions will be key to your success. Join our dynamic team and contribute to our mission of providing innovative integration solutions.

Otter seeks an Account Executive in Toronto to help grow its presence and strengthen client partnerships. This position centers on driving sales and building lasting relationships with clients. A real interest in sales and the ability to connect with people are key to success here. What you will do Increase sales and expand Otter’s reach within the Toronto market Build and sustain strong relationships with clients Provide attentive and dependable support to clients Requirements Interest in sales Strong interpersonal skills Located in Toronto

At HeyMilo, we are revolutionizing the hiring process with our innovative AI interviewers that engage candidates in authentic conversations. Our mission is to empower companies to enhance their recruitment speed and improve hiring decisions through advanced conversational AI technology.We collaborate closely with our clients to seamlessly integrate AI into their hiring workflows, ensuring that it yields measurable and impactful results.The RoleWe are seeking a proactive Technical Customer Success Manager (AI Tuning) to take charge of the performance and efficacy of our AI agents post-deployment.This position bridges engineering, product development, and customer success, allowing you to work hand-in-hand with clients to maximize the effectiveness of their AI agents, fostering continuous improvement.ResponsibilitiesEngage closely with clients and customer success teams to establish and monitor key success metrics.Analyze the performance of deployed AI agents and pinpoint areas for enhancement.Optimize prompts, workflows, and agent behaviors to achieve superior outcomes.Iterate on agent logic, tool utilization, and context management.Troubleshoot issues across prompts, integrations, and system functionalities.Transform real-world applications into actionable product and system enhancements.QualificationsSolid technical foundation with programming skills as needed.Extensive experience in prompt engineering and understanding LLM behavior.In-depth knowledge of agent systems, including tool invocation, context management, and orchestration.Frequent user of AI tools such as Cursor, Claude, Codex, etc.Skilled at debugging complex issues across AI and system layers.Strong ownership mentality and exceptional communication abilities.Adaptable to high-pressure situations and tight deadlines.Focused on achieving outcomes rather than merely completing tasks.Experience in implementing agent-based workflows or AI agents within enterprise settings is preferred.Familiarity with programming fundamentals, particularly in Python and JavaScript, is a significant advantage.Bonus SkillsExperience with conversational AI in various formats, including voice, SMS, or chatbots.

Join Halcyon as an Enterprise Account Executive in Toronto, where you will play a pivotal role in driving the growth of our business by nurturing relationships with key enterprise clients. Your expertise in sales and customer engagement will empower you to identify and capitalize on new opportunities within the enterprise sector.

At Relayfi, we are revolutionizing digital banking for entrepreneurs. Our platform empowers self-made business owners with the insights and tools they need to manage their finances effectively. We strive to eliminate financial uncertainty, turning cash flow into a reliable indicator for business growth.We are in search of a passionate Account Executive who is dedicated to driving the success of small businesses. If you possess a proven sales track record, thrive on nurturing relationships with business owners and their financial advisors, and are eager to make a meaningful impact, Relayfi is the right place for you!Joining our team means you will significantly contribute to our mission of providing innovative solutions to 29 million small businesses across North America. You will utilize your sales expertise to empower these businesses, forging lasting partnerships by understanding their unique challenges and delivering customized solutions.Key Responsibilities:Manage the complete sales cycle from prospecting to closing, driving new business through both inbound and outbound channels, and ensuring seamless post-sale activation.Become a subject matter expert in our products and the fintech industry to provide high-trust advisory support to business owners and their accountants/bookkeepers, aligning their objectives with our offerings.Articulate product capabilities into meaningful business value tailored to each client's goals.Surpass sales quotas by collaborating with team members to innovate and enhance the overall sales process.Collaborate cross-functionally with departments such as Business Development, Marketing, Revenue Operations, and Sales Enablement.Qualifications:Minimum of 2 years of full sales cycle or account management experience, preferably within the fintech sector or targeting SMBs, accountants, or bookkeepers.Demonstrated consultative sales approach with the ability to convert customer needs into clear business value.Experience in strategic account-based prospecting and generating outbound leads.

Join 1Password as we accelerate our growth! With over $400M in ARR, we’ve made the Forbes Cloud 100 list for four consecutive years and partnered with renowned names like Oracle Red Bull Racing and the Utah Mammoth.About 1PasswordAt 1Password, we are laying the groundwork for a secure and productive digital future. Our mission centers on enhancing employee productivity without sacrificing security, ensuring that every identity is verified, every application login is safe, and every device is trusted. We pioneered the market-leading enterprise password manager and created Extended Access Management, a groundbreaking cybersecurity category designed for modern workflows involving humans and AI. Trusted by over 180,000 businesses, ranging from Fortune 100 leaders to innovative AI companies, 1Password is a beloved brand in cybersecurity, emphasizing a human-centric approach in everything from product strategy to user experience.If you are enthusiastic about contributing to the digital safety of millions, eager to collaborate with a team of driven individuals, and ready to tackle complex challenges in a fast-paced environment, we want to hear from you. Join us in shaping a safer, simpler digital future.As part of our SMB (Small and Medium Business) Sales Team, your role as an SMB Account Executive will involve expanding our client base and nurturing existing relationships. You will manage a territory that includes target accounts and a portfolio of businesses with up to 1,000 employees. Your main focus will be on identifying new business opportunities, building a robust sales pipeline, and driving growth within the SMB sector. Additionally, you will be responsible for upselling within your existing accounts, leveraging our Extended Access Management Identity.The ideal candidate will excel in pipeline management, establishing multi-threaded relationships, and demonstrating proficiency in account planning, territory management, and value-based sales techniques.Role ExpectationsThis role is designated as in-office. Candidates are expected to work full-time from 1Password’s downtown Toronto office (3-5 days per week).What We Are Looking For:A minimum of 2 years of SaaS sales experience, preferably within the SMB sector...

Join Our Dynamic Team as an Enterprise Account Executive! In this pivotal role, you will: Conduct thorough needs assessments and effectively communicate Novisto’s unique value propositions and capabilities to potential clients. Foster collaboration across various stakeholders and coordinate efforts within diverse teams in target accounts. Drive new revenue growth by targeting Enterprise and Corporate prospects. Create compelling presentations with the assistance of our Sales Engineer. Prepare and respond to proposals, RFIs, negotiate, and finalize business terms to secure sales. Proactively reach out to prospects generated by our Account Development Representatives, marketing initiatives, or referrals. Ensure the timely delivery and successful implementation of our solutions tailored to customer objectives. Serve as a key point of contact for prospects and clients, enhancing their experience with our services. Keep our CRM system updated with accurate client information. Represent Novisto at industry events and conferences. Convey client insights to our product and marketing teams to drive continuous improvement.

Founded in 2017, Timescapes is dedicated to transforming the construction industry by providing shared visibility to simplify project management. Our innovative fixed-camera platform enables site teams and office personnel to gain real-time insights into job site progress, fostering transparency and facilitating quicker dispute resolution. With a growing global presence, Timescapes embodies a kiwi spirit—practical, humble, and committed to excellence.In the role of Account Executive, you will be responsible for a designated portfolio of target accounts across Canada and the USA. This full-cycle sales position requires you to actively prospect, generate leads, negotiate deals, and expand existing accounts to drive new business growth.Key ResponsibilitiesActively prospect and develop new business opportunities within your assigned list of target accounts, focusing on General Contractors, both existing and new clients.Expand our footprint within newly acquired accounts through a project-based sales strategy, identifying potential upsell opportunities and formulating effective account growth plans.Manage a robust sales pipeline, ensuring precise tracking of leads and opportunities, and executing all sales stages from initial contact to closure.Provide reliable sales forecasts and strive to meet and exceed weekly, monthly, and quarterly activity, funnel, revenue targets, and KPIs.Maintain and update all sales activities and customer interactions within Hubspot CRM to ensure data integrity and enhance reporting accuracy.Stay informed about industry trends and challenges within the Canadian construction sector. Attend relevant industry events to network and discover new opportunities. Cultivate strong relationships with key stakeholders and decision-makers, particularly Project Managers.

About From Day One:In a rapidly evolving business environment, From Day One serves as a pivotal media outlet and conference series dedicated to empowering companies to adapt and thrive while prioritizing people. Since our inception in 2018, we have engaged over 150,000 attendees, hosted numerous influential speakers, and produced impactful conferences across more than 20 major U.S. cities. Our distinctive, interdisciplinary approach brings together leaders from CSR, HR, marketing, communications, and civic sectors, alongside esteemed authors and journalists, to share innovative business strategies that create value for employees, clients, and communities alike.We also feature insightful reporting and opinion pieces from a network of distinguished journalists, led by our editor-in-chief, the acclaimed journalist Stephen Koepp.At From Day One, we seek highly self-motivated individuals with the potential to emerge as proactive leaders. Our team members, whom we refer to as “drivers,” are those who energize and inspire others. If you identify more as a passenger, this role may not align with your aspirations.As you consider applying, reflect on whether these characteristics resonate with you:You proactively inspire and energize your peers.You exhibit resourcefulness and ownership, avoiding excuses.You consistently strive for excellent results and enhance processes through engagement.You bring enthusiasm and urgency to your tasks.You approach challenges with optimism and enthusiasm.Our mission is to enhance the synergy between business and society, contributing to a brighter future. By maintaining a hopeful perspective, we not only motivate ourselves but also uplift those around us. We believe that fostering a belief in a better future is the first step towards actualizing it—for ourselves and others.Diversity and inclusion are fundamental to our mission, and we are dedicated to these values throughout our hiring process.

Are you ready to drive global connections?If you feel you may not meet every requirement listed, we still encourage you to apply. We are looking for candidates who excel in specific areas and possess a genuine interest in others.About the Position:We are on the lookout for a dedicated Enterprise Account Executive with a proven track record in sales and account management, preferably in open-source or enterprise software sectors. This role is crucial to our growth strategy, directly influencing our recurring revenue stability and expansion. It is an excellent opportunity for a sales professional experienced in acquiring new clients, nurturing existing relationships, and driving growth for early-stage enterprise solutions in a fast-paced, entrepreneurial environment.Your Responsibilities:Design and implement sales strategies aimed at enterprise-level clients, ensuring a strong pipeline that promotes sustained growth.Oversee the complete sales cycle, from initial prospecting to contract negotiations and deal closures, consistently achieving or surpassing revenue goals.Work closely with product, marketing, and customer success teams to guarantee a smooth sales process and alignment with customer expectations.Identify customer challenges and align our solutions to meet their needs, presenting tailored product demonstrations and presentations.Establish and maintain relationships with C-level executives and key decision-makers within target organizations, positioning yourself as a trusted advisor to enhance customer satisfaction and retention.Lead account planning initiatives by researching potential clients, analyzing industry trends, and formulating strategies to secure new business and expand existing accounts.Track and manage sales activities and outcomes, accurately forecasting opportunities while maintaining detailed records in CRM systems.Stay informed on industry trends, competitive offerings, and market shifts to effectively position our products and maintain a competitive advantage.Contribute to business growth efforts by providing insights to product and marketing teams to influence product development and go-to-market strategies.

Since our inception in 2009, the commerce landscape has undergone significant transformation, and so has Square. We began by empowering businesses to accept payments effortlessly, but we soon recognized that many sellers were hindered by disconnected, outdated tools that failed to integrate effectively.In response, we expanded our offerings to include software solutions that deliver integrated, omnichannel capabilities. Our aim is to assist sellers in optimizing their online sales, managing inventory, facilitating buy now, pay later options, scheduling appointments, engaging loyal customers, and efficiently hiring and compensating staff. By embedding financial services directly at the point of sale, we enable merchants to access business loans and manage cash flow seamlessly. Through Afterpay, we further our mission to provide tools that unlock significant value and growth, allowing sellers to attract the next generation of shoppers, increase order sizes, and compete on a broader scale.Today, we partner with sellers of all sizes, from large enterprises with complex operations to burgeoning businesses that started with Square and have expanded. As our sellers grow, so do our solutions. The opportunities ahead of us are vast. We are committed to building a significant and enduring business while supporting sellers globally in their journeys.The RoleSquare is assembling a top-tier, high-impact field sales team, and we are seeking an outstanding Territory Account Executive — a professional who consistently surpasses expectations, takes full ownership of their territory, and embodies Square’s mission of economic empowerment for businesses that require it the most.This role is designed for those who thrive in dynamic and challenging environments. Expect to spend the majority of your week in the field — engaging with businesses, performing live demonstrations, and confidently closing deals. The pace is fast, expectations are high, and your ability to operate strategically and decisively will determine your success.You will represent Square's presence and competitive advantage in one of our most promising markets — tasked with building a pipeline from the ground up, enhancing Square’s visibility within your community, establishing valuable partnerships, and aiding local businesses in their growth through our suite of leading software and hardware solutions.If you are inspired by impactful work, driven to excel, and eager to be part of a high-performance team with elevated standards, this role is tailored for you.

Welcome! We're glad you're here Are you on the lookout for an exciting new opportunity or just exploring your options? If so, you might just be in the right place!At Lightspeed, we are seeking a dynamic Outbound Account Executive to join our high-performing Retail sales team in North America. This full-cycle role entails generating leads through proactive outreach, scheduling meetings, and managing the sales process from initial contact to successful closure. Join us as we revolutionize the way business owners connect with their customers in the Hospitality, Retail, and Golf sectors.This position is hybrid, based out of our Toronto office (on Spadina), with in-office days required every Tuesday, Wednesday, and Thursday.

Who We AreSamsara (NYSE: IOT) is a trailblazer in the Connected Operations™ Cloud, a platform that empowers organizations reliant on physical operations to leverage Internet of Things (IoT) data for actionable insights, enhancing their operational efficiency. At Samsara, we are committed to improving the safety, efficiency, and sustainability of the physical operations that drive our global economy. Representing over 40% of global GDP, these sectors form the backbone of our society, including agriculture, construction, field services, transportation, and manufacturing. We are eager to assist in digitally transforming their operations on a large scale.Joining Samsara means playing a crucial role in shaping the future of physical operations and contributing to a diverse range of innovative product solutions, such as Video-Based Safety, Vehicle Telematics, Applications and Driver Workflows, and Equipment Monitoring. Being part of a recently public company provides you with the autonomy and support to make a significant impact as we build for the future.About the Role:This dynamic position involves introducing the Internet of Things to small and medium-sized enterprises, fostering Samsara's growth, and delivering the advantages of sensor data to our clients. Typical sales range from $5,000 to $20,000 and usually include proof of concepts, engagement with multiple stakeholders, intricate pricing negotiations, and interactions with owners and safety as well as operational managers.This position is based remotely in Canada.You Should Apply If:You want to make a difference in critical industries: Your contributions will lead to tangible outcomes—ensuring essential services remain operational, food availability in grocery stores, and most importantly, the safety of workers returning home.Your motto is #alwaysbeprospecting: The landscape of operations is vast. Often, your customers are in the field, and engaging them effectively means connecting with them directly through calls. Our top representatives continuously research to identify potential companies and contacts to broaden their pipeline.You possess a natural curiosity about business operations: One day you may discuss waste management, and the next, dive into the operations of a food distribution center. Our leading sales team members strive to understand the nuances of different industries.

Join Opendoor as a Senior Accountant, where you will play a vital role in managing our financial operations. Your expertise will contribute to accurate financial reporting, compliance, and strategic decision-making. In this position, you will collaborate with cross-functional teams to ensure financial integrity and support our growth initiatives.

About UsAt Heidi, we believe that healthcare deserves a harmonious approach that prioritizes continuity and human connection. We are pioneering an AI Care Partner that assists clinicians in delivering exceptional patient care.Our diverse team comprises doctors, engineers, designers, researchers, and creatives dedicated to crafting innovative tools that empower clinicians to focus on what truly matters: their patients.In just a year and a half, Heidi has reclaimed over 18 million hours for healthcare professionals, facilitating 73 million patient visits across 116 countries. Currently, we enable more than two million patient visits weekly around the globe.With nearly $100 million in funding, we are expanding our reach in the US, UK, Canada, and Europe, collaborating with leading health systems such as the NHS, Beth Israel Lahey Health, and Monash Health.