Sr Account Executive, Mid Market Payroll Sales

This role focuses on established regional restaurant groups, franchise organizations, and multi-unit operators with approximately 30–150 locations.

The Account Executive helps customers simplify payroll administration, improve labor visibility, and connect payroll and workforce data to their restaurant operations and financial results.

This is a full-cycle, consultative sales role responsible for account strategy, prospecting, discovery, demonstrations, business cases, proposals, negotiation, and close.

The successful candidate builds consensus across executive, finance, HR, payroll, and operations stakeholders while navigating complex buying processes and delivering a clear path to implementation.

This role focuses on established regional restaurant groups, franchise organizations, and multi-unit operators with approximately 30–150 locations.

The Account Executive helps customers simplify payroll administration, improve labor visibility, and connect payroll and workforce data to their restaurant operations and financial results.

This is a full-cycle, consultative sales role responsible for account strategy, prospecting, discovery, demonstrations, business cases, proposals, negotiation, and close.

The successful candidate builds consensus across executive, finance, HR, payroll, and operations stakeholders while navigating complex buying processes and delivering a clear path to implementation.

• Own the full sales cycle for mid-market payroll opportunities, from prospecting and account strategy through close and post-sale handoff.
• Build and manage a qualified pipeline through outbound prospecting, inbound leads, referrals, partner introductions, and cross-sell opportunities.
• Develop account plans for established regional groups, franchise organizations, and multi-unit operators with complex payroll needs.
• Lead discovery with executive, finance, HR, payroll, and operations stakeholders to identify business challenges, buying requirements, and desired outcomes.
• Deliver tailored demonstrations and business cases that connect R365 Payroll and Workforce Management solutions to measurable operational and financial value.
• Navigate multi-stakeholder buying processes, build consensus, manage mutual action plans, negotiate within approved guidelines, and close new business against quota.
• Identify and develop expansion opportunities within existing R365 accounting, operations, inventory, scheduling, and workforce management customers.
• Maintain accurate Salesforce and Gong records, including opportunity strategy, next steps, close plans, and revenue forecasts.
• Partner with Sales Engineering, Marketing, Product, Implementation, Customer Success, and internal subject matter experts to advance opportunities and ensure customer readiness.
• Deliver a clear, well-documented handoff to Implementation and Customer Success while representing Restaurant365 professionally in customer meetings and industry engagements.
• Shapes how their discipline uses AI, balancing innovation, risk, and data privacy in partnership with stakeholders.
• 3+ years of full-cycle B2B sales experience with a consistent record of quota attainment; SaaS, HCM, payroll, or workforce management experience strongly preferred.
• Experience selling to mid-market restaurant groups, franchise organizations, multi-unit operators, or similarly complex businesses.
• Direct experience selling payroll, workforce management, HCM, HR, accounting, or business management software is preferred.
• Working knowledge of payroll fundamentals, including tax filing, direct deposit, tip credit, overtime, PTO, garnishments, and compliance considerations.
• Proven ability to manage complex, multi-stakeholder sales cycles involving multiple active opportunities, business cases, and executive decision-makers.
• Strong prospecting skills and demonstrated success creating pipeline through outbound and inbound motions.
• Strong discovery, presentation, objection-handling, negotiation, and closing skills.
• Ability to build credibility with business owners, operators, finance leaders, payroll administrators, and HR stakeholders.
• Proficiency with Salesforce or a comparable CRM, with strong discipline around pipeline hygiene and forecast accuracy.
• Effective written and verbal communication skills, including the ability to explain complex payroll concepts clearly.
• High energy, self-motivated, goal-oriented, and comfortable working in a performance-driven environment.
• Demonstrated ability to collaborate with Sales Engineering, Customer Success, Marketing, Product, Implementation, and Revenue Operations.
• Trustworthy, ethical, and professional in all business dealings.
• Ability to work 100% remotely.
• Up to 15% travel may be required for customer meetings, conferences, team events, and offsites.
• AI fluency, including the ability to use approved AI tools responsibly to improve research, preparation, productivity, and customer impact while reviewing outputs for accuracy and protecting confidential information.
• This position has a salary range of $80,000-$120,000 + commission. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.
• Comprehensive medical benefits, 100% paid for employee
• 401k + matching

• Unlimited PTO + Company holidays
• Wellness initiatives