Enterprise Account Executive - Toronto

HiBob helps modern, mid-size businesses transform the way they manage people, giving HR and managers all they need to connect, engage, develop, and retain top talent. Since 2015, we’ve achieved consecutive triple-digit year-over-year growth, all backed by our amazing team of Bobbers from across the globe, making us the choice HRIS of over 4000 midsize and multinational companies.

Our HR platform is intuitive, data-driven, and built for the way people work today: globally, remotely, and collaboratively. Fast-growing companies across the globe rely upon Bob to help them create the best work experiences for their people.

Come and be you with us
Being a Bobber is all about being you. We want you to bring all parts of yourself to work, giving you the freedom and confidence to be the best you and do your best work. If that’s bubbly, shy, precise, funny, bold, kind, honest, brilliant, or anything in between, we’re waiting with open arms. Come join us.

Role Overview
As an Enterprise Account Executive, you will drive HiBob’s expansion across North America by identifying and closing new business in our Enterprise segment (companies with 1,000+ employees).

Working cross-functionally with Sales Engineering, Business Development, and Customer Success, you will own the end-to-end sales cycle—from strategic outbound prospecting to complex deal closing.

Responsibilities

• Drive Full-Cycle Enterprise Sales: Prospect, qualify, negotiate, and close new business opportunities within target enterprise accounts (1,000+ employees).
• Consultative Selling: Build relationships with key HR leaders and executive stakeholders, conducting thorough discovery to align HiBob's solutions with their core business priorities.
• Cross-Functional Collaboration: Partner closely with Sales Engineers to deliver tailored, value-driven product demonstrations and solution architectures.
• Pipeline Generation: Proactively build and maintain a robust sales pipeline through strategic outbound efforts, alongside marketing- and partner-generated leads.
• CRM & Data Hygiene: Maintain accurate pipeline forecasting, deal tracking, and key customer metrics within Salesforce.
• Industry Engagement: Represent HiBob at trade shows, conferences, and networking events to expand market visibility and build key partner relationships.

Requirements

• Experience: 3+ years of proven success closing complex B2B SaaS deals within mid-market or enterprise organizations.
• Track Record: Consistent history of meeting or exceeding ambitious revenue quotas selling into organizations with 1,000+ employees.
• Prospecting Mastery: Strong ability to generate self-sourced pipeline alongside inbound channels.
• Stakeholder Management: Experienced in navigating multi-stakeholder evaluations, overcoming objections, and securing buy-in from C-level executives.
• Sales Execution: Deep understanding of consultative sales methodologies, value selling, and contract negotiations.
• Mindset: High curiosity, resilience, and a collaborative spirit focused on continuous personal and team growth.

Benefits

At HiBob, our people are at the heart of everything we do.

We’re building a global village of ambitious, thoughtful, and talented Bobbers who want to do the best work of their careers. With vibrant Toronto and NYC offices along with remote teammates across North America, we’ve created an environment where people can be themselves, grow quickly, and make a real impact.

Joining HiBob means working alongside exceptional people while being supported with competitive compensation, comprehensive benefits, and pre-IPO equity, including the perks below.

Ownership & Financial

• Equity in a global, high-growth HR tech SaaS leader
• RRSP with a 3% company match effective the month following your start date
• $2,500 employee referral bonus

Health & Wellbeing

• Medical, dental, and vision coverage from day one
• $1,920 annual wellness stipend to support your physical and mental wellbeing(Lifestyle Spending Account)
• Annual Headspace membership and expanded wellness benefits

Workplace Flexibility

• Hybrid working model for Bobbers in the Toronto metro area
• Temporary work from anywhere for up to 2 months per year (after 6 months)

Work-Life Balance

• Generous paid time off and company holidays to rest, recharge, and enjoy
• Bob Balance Days – 4 additional days within a calendar year - Enjoy a company-wide long weekend at the beginning of each quarter
• Your birthday off — plus a special gift from us

Work From Home

• Home office allowance to set up your ideal workspace

Community & Culture

• Two paid Social Impact days each year to give back to causes you care about
• Frequent team and company social events, both in-person and virtual

If this sounds like something you’ve been looking for, we’d love to have you. Come on, join our village!

Location Eligibility: At this time, we are only considering talent in the Toronto Market.

Join HiBob and be part of a dynamic, people-centric organization where your impact will shape the future of work. Apply now and unleash your potential in a supportive, inclusive environment that celebrates your uniqueness.