Head of Sales

This is a fully remote position, open to applicants in Alabama, +26 more states.

📋 Description

• Develop and implement a thorough go-to-market strategy in collaboration with the CEO and Executive Leadership Team, incorporating competitive positioning, key milestones, and revenue growth objectives.

• Integrate inbound, outbound, and partner channels into a unified, high-performing GTM operation — creating the playbooks, handoffs, and conversion processes that link SDR → AE → Channel into a cohesive, disciplined engine.

• Formulate a long-term sales strategy that includes objectives, quotas, tracking systems, and analytics — and continuously enhance it as the business grows.

• Build, motivate, and oversee a top-tier sales organization; manage hiring, onboarding, ramp-up, coaching, performance evaluation, and succession planning across all sales positions.

• Inspire and hold the team accountable to meet monthly, quarterly, and annual revenue goals — cultivating a culture of accountability, urgency, and high performance without compromising collaboration.

• Develop exceptional talent within SDR and AE roles, investing in each individual’s growth while scaling the team effectively.

• Design, operationalize, and consistently refine the complete sales process for each motion, establishing clear KPIs, performance management frameworks, and operational discipline.

• Drive discipline in forecasting across direct and partner pipelines, focusing on accuracy, early risk detection, and data-informed decision-making.

• Implement and uphold cadences and tools (Salesforce, Gong) that foster visibility, repeatability, and accountability at all stages of the funnel.

• Collaborate closely with Marketing, RevOps, and Partnerships to ensure SDRs are engaging with high-quality leads, outbound lists are targeted to the Ideal Customer Profile (ICP), and partner connections yield predictable co-sell and referral revenue.

• Represent Tapcheck at industry forums, networks, and events — and engage with enterprise customers and key decision-makers.

• Act as a hands-on closer and executive sponsor for high-value deals, advocating for the Tapcheck vision at the most senior levels.

⛳️ Requirements

• Experience leading a multi-motion sales organization (SDR and AE) in a fast-growing B2B SaaS or tech-enabled services context, preferably in fintech, HRtech, or payments.

• Played a significant role in transitioning a company from founder-led or early-stage sales to a structured, process-oriented revenue engine — simultaneously building or scaling routes to market.

• Developed and refined repeatable sales processes, playbooks, and enablement programs that resulted in measurable improvements in conversion rates, ramp-up times, and quota achievement.

• Managed pipeline and forecasting across direct channels, with a proven track record of accuracy and early risk identification.

• Recruited, developed, and retained high-performing sales talent — including coaching individual contributors and, ideally, frontline leaders.

• Demonstrated strong analytical skills; utilized data to coach, prioritize, and enhance performance at both the team and individual levels.

• Established credible relationships with senior decision-makers and navigated intricate, multi-stakeholder deals.

• 8+ years of sales experience with at least 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 industry, and comfort in designing and evolving the sales tech stack architecture (Salesforce, Gong, and related tools).

🏝️ 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, including 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 embodies its values: humility, grit, and a genuine commitment to raising the bar every day.