Senior Account Executive, Mid Market Payroll Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of the entire sales cycle for mid-market payroll opportunities, encompassing prospecting, account strategy, closing, and post-sale handoff.

• Develop and maintain a qualified pipeline through outbound prospecting, inbound leads, referrals, partner introductions, and cross-sell initiatives.

• Create account plans for established regional groups, franchise organizations, and multi-unit operators with intricate payroll requirements.

• Conduct discovery sessions with executives, finance, HR, payroll, and operations stakeholders to pinpoint business challenges, purchasing needs, and desired outcomes.

• Provide customized demonstrations and business cases that link R365 Payroll and Workforce Management solutions to quantifiable operational and financial benefits.

• Navigate the complexities of multi-stakeholder buying processes, foster consensus, manage mutual action plans, negotiate within authorized guidelines, and secure new business in line with sales targets.

• Identify and cultivate expansion opportunities within the existing R365 customer base in accounting, operations, inventory, scheduling, and workforce management.

• Maintain precise records in Salesforce and Gong, detailing opportunity strategy, next steps, closing plans, and revenue forecasts.

• Collaborate with Sales Engineering, Marketing, Product, Implementation, Customer Success, and internal subject matter experts to advance opportunities and ensure customer preparedness.

• Provide a clear, well-documented handoff to Implementation and Customer Success while representing Restaurant365 professionally in customer meetings and industry events.

• Influence how the discipline adopts AI, balancing innovation, risk, and data privacy in collaboration with stakeholders.

⛳️ Requirements

• Minimum of 3 years of full-cycle B2B sales experience with a proven track record of meeting quotas; experience in SaaS, HCM, payroll, or workforce management is highly preferred.

• Experience selling to mid-market restaurant groups, franchise organizations, multi-unit operators, or similarly complex entities.

• Direct experience in selling payroll, workforce management, HCM, HR, accounting, or business management software is advantageous.

• Solid understanding of payroll fundamentals, including tax filing, direct deposit, tip credit, overtime, PTO, garnishments, and compliance considerations.

• Proven capability to manage intricate, multi-stakeholder sales cycles involving multiple active opportunities, business cases, and executive decision-makers.

• Strong prospecting abilities with a proven record of generating pipeline through outbound and inbound strategies.

• Excellent skills in discovery, presentation, objection handling, negotiation, and closing.

• Ability to build trust with business owners, operators, finance leaders, payroll administrators, and HR stakeholders.

• Proficiency in Salesforce or a similar CRM, with a strong emphasis on pipeline hygiene and forecast accuracy.

• Effective written and verbal communication skills, including the capability to clarify complex payroll concepts.

• High energy, self-motivated, goal-oriented, and comfortable in a performance-focused environment.

• Demonstrated ability to work collaboratively with Sales Engineering, Customer Success, Marketing, Product, Implementation, and Revenue Operations.

• Trustworthy, ethical, and professional in all business interactions.

• Ability to work completely remotely.

• Up to 15% travel may be necessary for customer meetings, conferences, team events, and offsite gatherings.

• Fluency in AI, including the responsible use of approved AI tools to enhance research, preparation, productivity, and customer impact while ensuring accuracy and protecting confidential information.

🏝️ Benefits

• Commission

• Comprehensive medical benefits, fully covered for employees

• 401k with company matching

• Equity Option Grant

• Unlimited PTO along with company holidays

• Wellness initiatives