Head of Sales

Tapcheck • Plano, TX

1d • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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).

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed