Hybrid Head of Sales, Mid Market

at CUBE

• Job title: Head of Sales, Mid Market
• Job type: Full Time
• Experience level: Lead
• Salary: Not specified
• Degree requirement: Bachelor's Degree
• Location requirements: Hybrid, New York City, United States

About the role

• Leading the mid-market sales team for a RegTech organization focused on financial solutions. Responsible for strategy formulation, execution, and driving revenue growth in a dynamic environment.

Responsibilities

• Develop and implement a scalable sales strategy tailored to the mid-market segment, driving consistent revenue growth.
• Recruit, lead, and coach a high-performing mid-market sales team. Establish clear goals, KPIs, and foster a culture of accountability, learning, and results.
• Oversee the full sales cycle for mid-market clients—from prospecting to proposal development, negotiation, and closing.
• Ensure team is building and maintaining strong relationships with senior decision-makers at mid-market firms to drive long-term value and retention.
• Work closely with Marketing, Product, and Customer Success to align on customer needs, competitive positioning, and go-to-market execution.
• Deliver accurate pipeline forecasting and sales performance reporting to senior leadership.
• Stay close to industry trends, customer feedback, and competitor activity to continuously refine sales strategy.

Requirements

• 6+ years of B2B sales experience, including 3+ years in a mid-market sales leadership role within financial services technology.
• Demonstrated success selling RegTech or adjacent compliance, risk, or governance solutions to mid-market financial institutions (e.g., banks, fintechs, asset managers, payments, or insurance firms).
• Proven ability to acquire, expand, and retain mid-market financial services accounts, with a strong understanding of regulatory drivers such as AML, KYC, sanctions, transaction monitoring, reporting, and audit requirements.
• Consistent track record of exceeding revenue targets, with hands-on ownership of full-cycle complex sales involving compliance, risk, legal, and executive stakeholders.
• Experience scaling and leading sales teams in high-growth RegTech or SaaS environments, including building repeatable sales processes, playbooks, and forecasting discipline.
• Strong consultative selling, negotiation, and relationship-management skills, with the ability to translate regulatory pain points into clear business value.
• Highly data-driven, with advanced skills in pipeline management, forecasting accuracy, and performance analytics.
• Deep familiarity with modern sales technology stacks, including CRM and revenue tools such as Salesforce, HubSpot, Outreach, Gong, and related enablement platforms.

Benefits

• Diversity, collaboration, and purpose are the heartbeat of our success.