Head of Sales

Summary

Join LearnLux, a leading provider of workplace financial wellbeing, as the Head of Sales. You will play a critical role in driving revenue growth, scaling sales operations, and expanding our customer base. Working closely with the CEO, you will develop and execute a high-impact sales strategy, build and manage a high-performing sales team, and foster partnerships. Responsibilities include optimizing the sales pipeline, refining go-to-market strategies, and ensuring effective scaling. This role reports to the CEO and is instrumental in shaping the future of LearnLux's sales organization. If you excel at leading teams, closing enterprise deals, and employing a data-driven sales strategy, this is the ideal opportunity.

Requirements

• 7+ years of sales leadership experience, ideally in B2B SaaS, fintech, or HR tech
• Proven ability to build and scale high-performing sales teams, with experience leading Account Executives
• Experience managing full-cycle enterprise sales, from prospecting to contract negotiation and deal closing
• Highly organized, persistent, and data-driven, with a strong desire to optimize processes and exceed revenue targets
• Strong familiarity with HubSpot CRM and sales automation tools, with experience optimizing workflows for efficiency
• Expertise in long, consultative sales cycles, requiring deep relationship-building and multi-stakeholder engagement
• Ability to sell to C-Suite executives at Fortune 500 companies, confidently presenting LearnLux’s value proposition
• Excellent copywriting and verbal communication skills, with an engaging presence on sales calls and demos
• Experience responding to and winning RFPs
• Adaptability and resourcefulness to thrive in a fast-paced startup environment without rigid corporate structures
• A passion for financial wellbeing and a deep understanding of the employer benefits landscape

Responsibilities

• Develop and implement a scalable sales strategy that aligns with LearnLux’s revenue goals, ensuring scalability
• Optimize inbound and outbound sales processes, track KPIs, and ensure a data-driven approach to pipeline growth and forecasting
• Build, mentor, and manage a high-performing sales team
• Establish clear playbooks, training programs, and a culture of accountability and collaboration to drive performance
• Oversee a structured sales pipeline using HubSpot CRM, ensuring accurate forecasting, lead nurturing, and seamless deal flow
• Assess market potential and identifies new business opportunities
• Engage directly with C-Suite executives at Fortune 500 companies, leading high-impact discovery calls, demos, and RFP processes to close complex, consultative sales
• Analyze sales data, monitor trends, and refine messaging to ensure LearnLux remains competitive and aligned with customer needs
• Partner with Marketing and Product teams to align sales initiatives with campaigns and product roadmaps, ensuring a unified go-to-market strategy
• Represent LearnLux at industry events, conferences, and networking opportunities, driving brand awareness and building key relationships

Benefits

• Remote-first company structure
• Medical, dental, and vision
• 401(k)
• Mental wellbeing (Talkspace)
• Financial wellbeing (LearnLux)
• Equity (Full-time employees)
• Flexible time off policy
• Paid sabbatical after 5 years of service
• A supportive, inclusive team culture
• Opportunities for continuous learning and growth at a fast-growing startup at the cutting edge intersection of financial wellness and technology