Account Executive, Mid Market Payroll Sales

Team: Growth

Location: Remote

Commitment: Full Time

Workplace Type: remote

How youll add value:

• 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. 

What youll need to be successful in this role:

• 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. 

R365 Team Member Benefits & Compensation

• 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
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives