Account Executive, Mid Market Payroll Sales

Restaurant365 is transforming how restaurants run their businesses. Today, we help more than 50,000 restaurant locations manage their finances, operations, and people. As AI changes what's possible, we're reimagining how restaurant back offices operate—automating routine work, helping teams make better decisions, and giving restaurant leaders more time to focus on growing their businesses.

We're transforming how we work, too. AI is changing how we build products, solve problems, and deliver results for our customers. We're embracing new ways of working, moving faster, and creating opportunities for our people to make a greater impact.

At Restaurant365, our culture is built on ownership, collaboration, and continuous improvement. We believe in challenging ourselves, learning every day, and working together to achieve great results. We're looking for people who are curious, take initiative, and want to grow while helping shape the future of an industry.

This role focuses on established regional restaurant groups, franchise organizations, and multi-unit operators with approximately 13–50 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.

How you'll add value

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Own the full sales cycle for mid-market payroll opportunities, from prospecting and account strategy through close and post-sale handoff.

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Build and manage a qualified pipeline through outbound prospecting, inbound leads, referrals, partner introductions, and cross-sell opportunities.

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Develop account plans for established regional groups, franchise organizations, and multi-unit operators with complex payroll needs.

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Lead discovery with executive, finance, HR, payroll, and operations stakeholders to identify business challenges, buying requirements, and desired outcomes.

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Deliver tailored demonstrations and business cases that connect R365 Payroll and Workforce Management solutions to measurable operational and financial value.

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Navigate multi-stakeholder buying processes, build consensus, manage mutual action plans, negotiate within approved guidelines, and close new business against quota.

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Identify and develop expansion opportunities within existing R365 accounting, operations, inventory, scheduling, and workforce management customers.

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Maintain accurate Salesforce and Gong records, including opportunity strategy, next steps, close plans, and revenue forecasts.

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

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

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Shapes how their discipline uses AI, balancing innovation, risk, and data privacy in partnership with stakeholders.

• Find opportunities to automate and improve how work gets done across your role with approved AI and other tools, choosing the right tool for each task, refining your prompts, and reviewing outputs for quality and time saved.

What you'll need to be successful in this role

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3+ years of full-cycle B2B sales experience with a consistent record of quota attainment; SaaS, HCM, payroll, or workforce management experience strongly preferred.

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

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Direct experience selling payroll, workforce management, HCM, HR, accounting, or business management software is preferred.

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Working knowledge of payroll fundamentals, including tax filing, direct deposit, tip credit, overtime, PTO, garnishments, and compliance considerations.

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

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Strong prospecting skills and demonstrated success creating pipeline through outbound and inbound motions.

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Strong discovery, presentation, objection-handling, negotiation, and closing skills.

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

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Proficiency with Salesforce or a comparable CRM, with strong discipline around pipeline hygiene and forecast accuracy.

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Effective written and verbal communication skills, including the ability to explain complex payroll concepts clearly.

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High energy, self-motivated, goal-oriented, and comfortable working in a performance-driven environment.

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

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Trustworthy, ethical, and professional in all business dealings.

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Ability to work 100% remotely.

• Curiosity and eagerness to use AI in your daily work, backed by hands-on experience, a good sense of what generative AI can and can't do, and the judgment to verify its outputs.

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Up to 15% travel may be required for customer meetings, conferences, team events, and offsites.

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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

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Internal Employees - R365 is committed to growing talent from within.  If you see a role that excites you and you meet the qualifications, we encourage you to apply -regardless of your current location or work arrangement.  Reach out to your People Business Partner if you have questions.

DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.