Head of Sales

LearnLux is the leading provider of workplace financial wellbeing that blends fiduciary digital planning with access to one-on-one guidance from Certified Financial Planner™ professionals. LearnLux's award-winning program equips employees with a financial plan to guide them through decision points like budgeting, paying down debt, electing benefits, understanding equity compensation, starting a family, buying a home, saving for retirement, and more. Advanced reporting keeps our partners in the know, and drives results like reduction in financial stress, increased productivity, reduced employee turnover, greater use of pretax products, on-time retirement, and healthcare savings. LearnLux members feel great about their money, allowing their work and wellbeing to thrive. We’re a remote-first company, backed by prominent operators such as Ashton Kutcher’s fund Sound Ventures and Salesforce CEO Marc Benioff.

The Head of Sales plays a critical role in driving revenue growth, scaling sales operations, and expanding our customer base. You’ll work closely with the CEO and leadership team to develop and execute a high-impact sales strategy, build and manage a high-performing sales team, and drive partnerships that accelerate business growth.

You’ll be responsible for optimizing the sales pipeline, refining go-to-market strategies, and ensuring that LearnLux continues to scale effectively. This role reports to the CEO and will be instrumental in shaping the future of LearnLux’s sales organization. If you thrive on leading teams, closing enterprise deals, and executing a data-driven sales strategy, this role is for you.

WHAT YOU'LL DO:

• 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

WHAT YOU SHOULD HAVE:

• 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

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

LearnLux strives to be an inclusive workplace and values learning from and engaging across different perspectives. Women, people of color, LGBTQIA+ individuals, and members of other minority or marginalized groups are strongly encouraged to apply.

LearnLux is proud to be an equal opportunity employer and does not discriminate against candidates on the basis of race, ethnicity, color, national origin, age, religion, sex, gender, sexual orientation, gender identity, marital status, disability, or veteran status.

We are committed to fostering an environment that embraces diversity and inclusion and are seeking candidates from a variety of backgrounds, experiences, abilities, and perspectives to join our team. If you are interested in this opportunity but not sure if you fit this role, please apply and include a note to let us know of your interest. We’re excited to speak with you about joining our team!