Director, Head of Revenue Operations at Hiive

Recognized as one of Canada’s top startups two years in a row — climbing from #4 in 2024 to #2 in 2025 — Hiive is a fintech/marketplace startup connecting buyers and sellers of stock in venture-backed pre-IPO companies🚀. Thanks to our industry-leading technology and best-in-class sales and trading team, we are home to the fastest-growing marketplace for the stock of “unicorns” on the planet. As a profitable and rapidly growing business backed by US venture capital investors, we are seeking to scale our high-performing team. Interested in learning more about life at Hiive? Check out our careers page [Upgrade to PRO to see link] to see how you can grow with us! As the Director, Head of Revenue Operations at Hiive, you will architect the go-to-market systems at a company poised for explosive growth. We are seeking an ambitious, strategic, AI-native, and accomplished leader with a growth mindset who has a proven track record of building and scaling a world-class GTM Ops, Sales Ops, or Revenue Ops function and team within a high-performing startup or innovative financial services organization. This is a career-transforming opportunity to leave an indelible mark on a rapidly evolving industry. You will play a lead role in strategizing, building, and leading the infrastructure that underpins our high-performing GTM teams. You will be a key partner to our executive team, directly influencing our go-to-market strategy and execution. Your systems-thinking approach will be instrumental in creating a seamless, scalable, and data-driven revenue engine that propels Hiive to new heights. In this role, your responsibilities would include: - Leadership and architecture of a next-generation, AI-enabled go-to-market system, designed and built with the support of GTM engineers to radically enable our GTM teams, particularly Sales and Trading. - Ownership of end-to-end GTM operations, designing and optimizing operating models across Sales, Trading, Marketing, and revenue-adjacent teams to ensure clear ownership, seamless handoffs, and consistent execution across the full customer lifecycle. - Sales and lead generation technology stack ownership. Plan, procure, maintain, optimize, and oversee the entire sales technology stack, including Salesforce, Airtable, outbound sales tools, research platforms (such as Pitchbook, Rocket Reach, and Crunchbase), and communication systems, ensuring the ecosystem is efficient, scalable, and future-ready. - CRM and data management mastery. Develop and maintain CRM systems and processes, along with adjacent tools, to ensure high data integrity, usability, and adoption. Streamline workflows, automate where possible, and ensure data is a strategic asset across all GTM functions. - Strategic GTM analysis and reporting. Partner with Sales, Marketing, and executive leadership to establish and manage an operational cadence for forecasting, pipeline reviews, capacity planning, and performance management. Build and maintain dashboards and reporting that provide clear visibility into GTM performance at both team and individual levels. - Research and lead generation leadership. Strategize approaches to and lead a high-performing team of lead generation researchers, continuously innovating to expand reach, accelerate pipeline, and improve lead quality. - Intelligent lead analysis and optimization. Implement and manage lead scoring models, routing logic, and automation rules to maximize conversion efficiency and ensure the right opportunities reach the right teams at the right time. - GTM planning and execution support. Partner with leadership on territory design, coverage models, capacity planning, incentive alignment, and campaign execution to support aggressive growth targets. - Process improvement and innovation. Collaborate with Sales, Marketing, Trading, and other GTM-adjacent teams to identify, analyze, and enhance GTM processes, prioritizing efficiency, scalability, and reduction of technical and operational debt through automation and AI-enabled workflows. - Sophisticated campaign management. Set up, implement, and analyze large-scale outbound sales campaigns, continuously optimizing for impact, conversion, and ROI. - Dynamic team leadership and coaching. Build, lead, and mentor the Revenue Operations team, fostering a culture of accountability, innovation, and high performance while investing deeply in the development and retention of top talent. Required Skills: - 8+ years of progressive experience in GTM, revenue, or sales operations, with at least 2 years in a leadership role building and scaling a function and team. - Proven success building and leading GTM or revenue operations within a high-growth startup or innovative financial services organization. - Demonstrated experience operating across multi-functional GTM teams, including Sales, Marketing, and customer-facing groups, in complex environments. - Deep expertise in Salesforce administration, configuration, and optimization, with a strong understanding of CRM-driven GTM processes. - Experience leveraging AI-enabled workflows and automation within GTM or revenue operations. - Proficiency with outbound sales platforms, CRM systems, and reporting or business intelligence tools. - Strong analytical capabilities with the ability to translate complex data into actionable insights for executive leadership. - Hands-on experience driving process improvement, automation, and scalable GTM systems. - Strong understanding of sales methodologies, forecasting, pipeline management, and performance metrics. - Proven people leader with a passion for mentorship, talent development, and building high-performance teams. - Excellent communication and stakeholder management skills, with the ability to influence across all levels of the organization. - Systems thinker with the ability to design integrated solutions across people, process, and technology. - Self-starter with a strong sense of ownership, accountability, and bias toward action. - Growth mindset with a continuous drive to learn, adapt, and innovate. Preferred Skills: - Experience in a fintech, marketplace, or capital-markets-adjacent environment. - Hands-on experience with Airtable for operational workflows and data management. - Familiarity with advanced BI and data visualization tools such as Omni, Tableau, Looker, or Power BI. - Understanding of financial services regulations and compliance considerations within GTM motions. - Experience supporting B2B GTM teams with complex, multi-stakeholder sales cycles. Compensation, Benefits, & Perks:  - Highly competitive salary commensurate with experience and contribution. - Opportunity to participate in ownership of a rapidly growing early-stage startup through our employee stock option plan. - Comprehensive 100% employer-paid health and dental premiums, a health and personal spending account. - A dedicated desk in our Vancouver, BC HQ, in the heart of downtown, with a fridge stocked with healthy snacks and drinks, an onsite gym, and a gorgeous rooftop amenity. - Enjoy a $20-per-day commuter benefit for every day you work in our Vancouver HQ. - An engaging social calendar, including bi-weekly catered lunches, bi-weekly “Friday bar,” team workouts, annual summer party, and holiday party, two “onsite” all-team retreats each year, semi-annual team-building events, and Hiive Womens’ Network events. - Significant opportunities for growth into team leadership and management roles. - Entrepreneurial culture and a small and dynamic team. - Sponsorship, immigration, and relocation for exceptional candidates. Hiive is committed to fostering an inclusive workplace where all individuals have an opportunity to succeed.