About the JobTapcheck 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 DoSales 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).
CompensationCompensation 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.
