Account Executive, Enterprise, 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.

About Us

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. Restaurant365 is transforming restaurant operations with a cloud-based platform that unifies accounting, back office, workforce management, inventory, payroll, and more.

What You'll Do

We are looking for an enterprise seller who is motivated by winning the largest and most complex deals in the company—and who can turn that ambition into meaningful customer outcomes. As an Enterprise Account Executive, you will lead high-value sales opportunities with large national restaurant brands and franchise systems. You will engage executive stakeholders, navigate complex buying environments, sell across multiple product lines, displace legacy software, and build the alignment required for systemwide adoption.

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

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

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

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

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

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

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

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

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

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

- 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.

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

- Other duties as assigned.

What You'll Need

- 5+ years of full-cycle B2B sales experience with a strong and consistent record of quota attainment; SaaS or HCM/payroll software sales strongly preferred.

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

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

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

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

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

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

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

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

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

- Trustworthy, ethical, and professional in all business dealings.

- Must be able to work 100% remote.

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

What Success Looks Like

- 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.

Benefits & Perks

- This position has a salary range of $100,000 - $120,000 + commission.

- Ability to work remote or hybrid.

- Comprehensive medical benefits.

- 401k + matching.

- Equity Option Grant.

- Unlimited PTO + Company holidays.

- Wellness initiatives.

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