Head of Sales, Mid Market

CUBE • New York, NY

3d

About The Position

The Head of Mid-Market Sales will be responsible for our mid-market sales function, focusing on acquiring and expanding relationships with fast-growing financial services firms. This role requires a hands-on sales leader who can balance strategy with execution. You’ll be responsible for driving pipeline development, helping to close deals across a range of mid-market clients, and building a high-performing sales team that thrives in a fast-paced, high-growth environment.

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.

Responsibilities

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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees