Account Executive, Mid Market Payroll Sales

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365 ’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!

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.

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 sta