Senior Sales Executive - SafeSend & SurePrep

Summary of the Role

We’re seeking a high-performing sales leader to drive strategic growth for our award-winning and market-leading SafeSend Returns (SSR) and SurePrep solutions. As a Senior Sales Executive, you’ll operate in an overlay sales role, partnering closely with our Tax Workflow sales representatives, who own the full sales bag. You’ll lead complex sales cycles, build trusted relationships with accounting firms, and deliver integrated solutions that enhance client experience and operational efficiency. This role is ideal for a seasoned professional who thrives in a collaborative, fast-paced environment and is passionate about solving customer challenges through technology.

About the Role

As a Senior Sales Executive, you will:

• Serve as a subject matter expert on SafeSend Returns (SSR) and SurePrep, articulating their value to accounting firms and their clients.
• Operate in an overlay capacity, partnering with Tax Workflow sales reps to co-develop strategies, align on territory plans, and jointly drive sales success.
• Lead the full sales cycle—from opportunity identification to close—including handling objections, negotiating terms, and addressing EULA concerns.
• Prepare and present sales forecasts, territory insights, and performance metrics.
• Generate and qualify leads through multiple channels including webinars, tradeshows, firm lists, sales campaigns, and cross-selling within the existing SafeSend and SurePrep customer base.
• Collaborate on pricing strategies, product quotes, and CRM best practices to ensure accurate and timely data capture.
• Consistently meet or exceed monthly, quarterly, and annual sales goals.
• Act as a mentor and resource to Associate and Sales Executives, contributing to team development and knowledge sharing.

About You as a Candidate

You bring:

• 5+ years of successful sales experience in software solutions, preferably in B2B or professional services environments.
• A high school diploma (required); college degree (preferred).
• Proven ability to lead complex sales cycles and build long-term client relationships.
• Strong collaboration skills and experience working in matrixed sales environments.
• Excellent communication, negotiation, and presentation skills with senior decision-makers.
• A strategic mindset with the ability to align product solutions to customer business needs.
• Familiarity with accounting and tax firm operations (preferred).
• Strong organizational skills and responsiveness.
• A positive, energetic attitude with a drive for results and continuous improvement.
• Experience with Salesforce CRM or similar tools (preferred).

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What’s in it For You?

• Hybrid Work Model: We’ve adopted a flexible hybrid working environment (2-3 days a week in the office depending on the role) for our office-based roles while delivering a seamless experience that is digitally and physically connected.

• Flexibility & Work-Life Balance: Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset. This builds upon our flexible work arrangements, including work from anywhere for up to 8 weeks per year, empowering employees to achieve a better work-life balance.

• Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow’s challenges and deliver real-world solutions. Our Grow My Way programming and skills-first approach ensures you have the tools and knowledge to grow, lead, and thrive in an AI-enabled future.

• Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.

• Culture: Globally recognized, award-winning reputation for inclusion and belonging, flexibility, work-life balance, and more. We live by our values: Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Fast / Learn Fast, and Stronger Together.

• Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get involved with pro-bono consulting projects and Environmental, Social, and Governance (ESG) initiati