Enterprise Account Executive, 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.

The Account Executive, Enterprise Accounts – Payroll is responsible for driving new payroll revenue by selling Restaurant365’s Payroll and Workforce Management solutions & partner HCM solutions to enterprise and strategic restaurant accounts. This role targets multi-unit restaurant operators, franchise organizations, and emerging chains — helping them consolidate payroll onto a purpose-built restaurant platform that connects labor directly to their P&L. As a specialist seller within the R365 Strategic Accounts team, this position partners closely with Account Executives, Customer Success, and Sales Engineers to identify, develop, and close payroll opportunities across both net-new and existing accounts.

Responsibilities

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Own and drive net-new payroll sales into strategic restaurant accounts, including national and regional franchise brands

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Prospect and develop a pipeline of qualified payroll opportunities through outbound outreach, inbound referrals, and cross-sell motions within the existing R365 customer base

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Lead discovery conversations with HR, Payroll, Finance, and Operations leaders to uncover workforce pain points and align R365 Payroll solutions to business outcomes

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Execute a consultative, value-based sales process from first contact through close, including demos, proposals, and negotiation

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Partner with Sales Engineers to deliver compelling platform demonstrations tailored to payroll and workforce workflows in the restaurant industry

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Develop and present business cases quantifying the ROI of migrating to R365 Payroll — including labor cost reduction, compliance risk mitigation, and administrative time savings

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Collaborate with the broader Strategic Accounts team to identify payroll expansion opportunities within existing R365 accounting and operations customers

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Maintain accurate pipeline data, activity logs, and revenue forecasts in Salesforce & Gong

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Stay current on payroll compliance regulations relevant to the restaurant industry, including federal, state, and local wage laws, tip credit rules, and overtime requirements

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Represent R365 as a payroll subject matter expert at industry events, prospect meetings, and customer-facing engagements

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Provide a smooth handoff to Implementation and Customer Success teams post-sale, ensuring expectations are set and the customer is set up for long-term success

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Demonstrate adaptability and a high level of accountability as part of a rapidly scaling sales organization

• 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.

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Other duties as assigned

Qualifications

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2+ years of proven experience selling payroll software as a core component of the solution, including payroll processing, tax administration, compliance, and related workforce functionality is required.

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Direct experience selling payroll, workforce management, or HCM solutions (e.g., ADP Workforce Now, Paylocity, Paycom, Paychex, UKG, Gusto, or comparable platforms)

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Working knowledge of payroll fundamentals: tax filing, garnishments, direct deposit, tip credit, PTO accruals, and multi-state compliance

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Experience selling into restaurant, hospitality, or multi-unit retail organizations is a significant advantage

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Proficiency with Salesforce or comparable CRM — disciplined in pipeline hygiene and forecasting accuracy

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Relationship-based seller with the ability to build trust with HR, Finance, and C-suite stakeholders simultaneously

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Strong discovery skills — ability to ask the right questions, listen actively, and connect prospect pain to platform value

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Effective communicator, both written and verbal, with the ability to translate complex payroll and compliance concepts into clear business language

• 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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High energy, self-motivated, goal-driven, and capable of thriving in a fast-moving, high-growth environment

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Demonstrated ability to work cross-functionally with Sales Engineers, Customer Success, Marketing, and Product teams

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Trustworthy, ethical, and professional in all business dealings

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Must be able to work 100% remote

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Up to 20% travel required for customer meetings, conferences, and team offsites

What Success Looks Like

Milestone

Expectation

30 Days

Complete R365 payroll product certification; develop territory plan and initial pipeline of qualified prospects

60 Days

Active pipeline established across net-new and cross-sell motions; first discovery calls and demos delivered

90 Days

First payroll deal closed or in late-stage negotiation; consistent Salesforce hygiene and weekly forecast accuracy

Year 1

Attain or exceed payroll ARR quota; build repeatable playbook for R365 Payroll in the restaurant vertical

R365 Team Member Benefits & Perks

• This position has a salary range of  $ 100,000 - $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.

• Ability to work remote or hybrid

• Comprehensive medical benefits

• 401k + matching

• Equity Option Grant

• Unlimited PTO + Company holidays

• Wellness initiatives

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.