Head of Sales

About the Role

Tapcheck is seeking a Head of Sales to develop, lead, and expand a high-achieving sales organization, encompassing both Sales Development Representatives (SDR) and Account Executives (AE). Reporting directly to the CEO, you will be responsible for crafting and executing a comprehensive revenue strategy to transition the company beyond product-market fit toward a scalable revenue engine designed for growth. This position involves hands-on leadership, owning pipeline generation, deal closure, partner-driven revenue, and managing the teams responsible for these outcomes.

This role supports both remote and hybrid work arrangements. Employees within 30 miles of Plano, TX must work onsite from Tuesday through Thursday weekly. Remote candidates are preferably located in selected states including AL, AZ, CA, CO, DC, DE, FL, GA, ID, IL, LA, MI, MA, MO, NC, NH, NJ, NV, NY, PA, OR, OH, RI, SC, TX, UT, VA, WA, or WI.

Key Responsibilities

• Design and implement a detailed go-to-market strategy alongside the CEO and executive leadership, focusing on competitive positioning, milestones, and revenue objectives.
• Integrate inbound, outbound, and partner sales channels into a unified, efficient GTM framework that seamlessly coordinates SDRs, AEs, and channels with defined playbooks and processes.
• Develop and continually refine a long-term sales plan covering strategy, quotas, tracking, and analytics to support business scaling.
• Recruit, mentor, and oversee a top-tier sales team, managing hiring, onboarding, coaching, performance evaluations, and succession planning across all sales functions.
• Drive accountability, motivation, and high performance by managing the team to meet monthly, quarterly, and annual revenue goals while fostering collaboration.
• Implement and improve sales processes, KPIs, and operational discipline to optimize every sales motion.
• Lead forecasting efforts for both direct and partner sales pipelines emphasizing accuracy, early risk detection, and data-driven decisions.
• Manage deployment of sales tools (Salesforce, Gong) to enhance visibility and accountability throughout the sales funnel.
• Collaborate with Marketing, Revenue Operations, and Partnerships to ensure quality lead generation and conversion through co-selling and referral programs.
• Represent Tapcheck at industry events and senior-level enterprise meetings; act as an executive sponsor and hands-on closer for key deals.

Experience and Qualifications

• Extensive leadership of multi-channel sales teams (SDR and AE) in high-growth B2B SaaS or technology services industries, preferably fintech, HR tech, or payments.
• Proven success transitioning companies from founder-led sales to established, process-oriented revenue engines with scalable routes to market.
• Expertise in developing repeatable sales processes, playbooks, and enablement that improve conversion, onboarding speed, and quota achievement.
• Strong background in pipeline ownership and revenue forecasting with demonstrated accuracy and proactive risk management.
• Demonstrated ability to recruit and nurture sales talent and, when possible, frontline leadership.
• Analytical proficiency to use data effectively for coaching and optimizing sales team performance.
• Established credibility engaging senior stakeholders to manage complex, multi-party sales negotiations.
• Minimum 8 years of sales experience including at least 3 years in sales leadership with direct team oversight.

Preferred Experience

• Familiarity selling into human resources, payroll, or employee benefits sectors.
• Knowledge of earned wage access or financial wellness industries.
• Experience architecting and managing sales technology stacks such as Salesforce and Gong.

About Tapcheck

Tapcheck offers a digital platform providing easy access to earned wages before payday at no cost to employers. This solution supports employee financial wellbeing by enabling immediate transfer of earned pay, reducing reliance on high-interest loans or employer advances. The company values humility, resilience, continuous improvement, and personal growth, fostering a collaborative and high-performance culture.

Company Values

• Humility: Emphasizing respect, openness, and positive collaboration.
• Grit: Demonstrating determination and embracing challenges as growth opportunities.
• Raising the Bar: Pursuing ongoing improvements and excellence.
• Striving for Growth: Encouraging personal and professional development and initiative.

Employee Benefits

• Mission-driven work improving financial flexibility and reducing debt burden for workers.
• Flexible unlimited paid time off policy without accrual limits.
• Ten paid holidays including Christmas Eve and New Year's Eve.
• Comprehensive health insurance including medical (Blue Cross Blue Shield of Texas PPO and HDHP with HSA option), dental and vision coverage through MetLife.
• Additional benefits including FSA, basic life and AD&D insurance, and Employee Assistance Program.
• 401(k) plan with full employer matching up to 3% after 90 days via Mutual of America.
• A values-driven team culture focusing on humility, grit, and continuous improvement.

Compensation and Equal Opportunity

Tapcheck offers competitive compensation aligned with your role and market benchmarks, reflecting your impact within the organization. Specific details are provided during the hiring process. The company is committed to equal employment opportunity and prohibits any discrimination or harassment on protected grounds in recruiting, hiring, promotion, compensation, and employment conditions.