Head of Sales

About the Job Tapcheck is looking for a Head of Sales to build, lead, and scale a high-performing, volume-driven sales organization across SDR and AE teams. Reporting directly to the CEO, you will own the full go-to-market revenue strategy — moving us from post-product-market fit to a repeatable, scalable revenue engine built for growth. This is a hands-on sales leadership role with direct accountability for pipeline generation, deal execution, partner-sourced revenue, and the team that makes it all happen. This role offers both a remote and hybrid option. Employees located within 30 miles of Plano, TX are required to be in-office Tuesday through Thursday each week. If remote, ideally candidates will sit in the following states: 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, WI. What You’ll Do Sales Strategy & GTM Execution Define and execute a comprehensive go-to-market strategy in close partnership with the CEO and Executive Leadership Team, including competitive positioning, key milestones, and revenue growth targets. Unify inbound, outbound, and partner channels into one high-output GTM motion — building the playbooks, handoffs, and conversion processes that tie SDR AE Channel into a single, disciplined engine. Create a long-term sales plan encompassing strategy, quotas, tracking mechanisms, and analytics — and continuously refine it as the business scales. Team Leadership & Development Build, inspire, and manage a best-in-class sales organization; own hiring, onboarding, ramp, coaching, performance management, and succession planning across all sales roles. Lead, motivate, and hold the team accountable to monthly, quarterly, and annual revenue targets — fostering a culture of accountability, urgency, and high performance without sacrificing collaboration. Develop top-tier talent across SDR and AE, investing in each individual’s growth while scaling the team efficiently. Operations, Metrics & Forecasting Design, operationalize, and continuously improve the end-to-end sales process for each motion, with clear KPIs, performance management frameworks, and operational rigor. Drive forecasting discipline across direct and partner pipelines, with an emphasis on accuracy, early risk identification, and data-informed decision-making. Implement and enforce cadences and tooling (Salesforce, Gong) that create visibility, repeatability, and accountability at every level of the funnel. Cross-Functional & Market Presence Partner closely with Marketing, RevOps, and Partnerships to ensure SDRs are working high-quality leads, outbound lists are targeted to ICP, and partner connections convert to predictable co-sell and referral revenue. Represent Tapcheck at industry forums, networks, and events — and in front of enterprise customers and key decision-makers. Serve as a hands-on closer and executive sponsor on high-value deals, evangelizing the Tapcheck vision at the most senior levels. What You’ve Done Led a multi-motion sales organization (SDR and AE) in a high-growth B2B SaaS or tech-enabled services environment, ideally in fintech, HRtech, or payments. Played a meaningful role in moving a company from founder-led or early-stage sales to a structured, process-driven revenue engine — building or scaling routes to market simultaneously. Built and refined repeatable sales processes, playbooks, and enablement programs that drove measurable improvements in conversion rates, ramp time, and quota attainment. Owned pipeline and forecasting across direct channels, with a track record of accuracy and early risk identification. Hired, developed, and retained strong sales talent — including coaching individual contributors and, ideally, frontline leaders. Demonstrated strong analytical acumen; used data to coach, prioritize, and optimize performance at the team and individual level. Built credible relationships with senior decision-makers and navigated complex, multi-stakeholder deals. 8+ years of sales experience with 3+ years in sales leadership, including direct team management. Preferred Experience selling into HR, payroll, or benefits ecosystems. Familiarity with the earned wage access or financial wellness space. Comfort designing and evolving sales tech stack architecture (Salesforce, Gong, and adjacent tools). About Tapcheck Tapcheck is a digital platform offering an easy and convenient way to access on-demand earnings early. Available at no cost to employers, our app-based on-demand pay solution helps relieve the financial stress that many employees experience on a daily basis. The Tapcheck team is passionate about our mission to improve financial wellness and boost business productivity. By giving workers the ability to transfer wages they’ve earned directly to their bank account or pay card without waiting for payday, Tapcheck eliminates the need for high-interest payday loans or employer-funded cash advances. How We Get Things Done Our core values act as a steadfast guide, directing our decisions and anchoring our actions. We consider these values non-negotiable, especially when it comes to our hiring process. Humility: We believe in the power of humility. We value team players who are down-to-earth, respectful, and open to learning from others. Our employees approach challenges with a positive attitude, acknowledging their strengths and weaknesses while celebrating the achievements of their colleagues. Grit: We admire individuals with grit – those who demonstrate unwavering determination and resilience in the face of obstacles. At Tapcheck, we take pride in overcoming challenges together, pushing the boundaries of what is possible, and embracing failure as an opportunity for growth. Raising the Bar: Continuous improvement is at the heart of our culture. We are committed to setting high standards and pushing ourselves to exceed them. We seek employees who are innovative and strive for excellence, constantly seeking ways to enhance our products, services, and processes. Striving for Growth: We foster an environment that encourages personal and professional development. Our employees are driven to learn, grow, and adapt to new circumstances. We support individuals who take initiative, seek out new challenges, and actively contribute to their own growth and the growth of the company. Why Join Tapcheck? Mission that matters. We’re changing how Americans access their pay — giving workers financial flexibility without the debt trap of payday loans. Flexible PTO. No accrual caps, no counting days. Take the time you need. 10 paid holidays. Including both Christmas Eve and New Year's Eve. Comprehensive health coverage. Medical through Blue Cross Blue Shield of Texas (PPO and HDHP options, HSA-eligible with employer contribution), plus dental and vision through MetLife. FSA, Basic Life/AD&D, and an Employee Assistance Program (EAP). 401(k) with a 100% match up to 3% of your salary, through Mutual of America. Eligible after 90 days. A team that lives its values. Humility, grit, and a genuine drive to raise the bar — every day. Compensation Compensation at Tapcheck is competitive and benchmarked to your role and the market. We’re committed to a total rewards package that reflects your impact. Full details are shared as part of our hiring process. Tapcheck, Inc. provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. #J-18808-Ljbffr