Account Executive, Mid-Market

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, Mid-Market sells the R365 platform to mid-market restaurant groups, with 13 to 50 units. This is a full-cycle, consultative role that owns complex deals, builds consensus across executive, finance, operations and HR stakeholders, and guides other sellers within their domain. The seller works independently on assigned opportunities and brings in sales leadership for strategy and pricing on the largest deals while keeping ownership of the opportunity. The sales cycle is more complex than Commercial, with several decision makers, a formal evaluation, and a customer-specific business case, so this role is expected to show a higher level of skill in discovery, multi-threading, and negotiation. This is not an entry-level sales role; prior quota-carrying B2B sales experience is required. Restaurant or hospitality leadership experience alone does not meet this requirement.

Responsibilities

• Own the full sales cycle for mid-market opportunities, from account planning and prospecting through close and handoff to implementation.

• 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.

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

• Deliver tailored demonstrations and business cases that connect R365 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 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 Revenue Operations to advance opportunities and ensure customer readiness.

• Engage sales leadership for guidance on complex deal strategy, pricing and executive alignment while keeping ownership of the opportunity.

• Guide other sellers within their domain by sharing deal approaches, discovery techniques and business case examples.
• 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.

Qualifications and Experience

• 3-5 years of full-cycle B2B SaaS sales experience, with a track record of closing deals in the 60,000 –200,000 ACV Range.

• A consistent record of quota attainment (e.g., consistently achieving 100%+ of a 600,000- 1,000,000+ annual quota) in full-cycle B2B sales, with experience selling SaaS or technology solutions to mid-market restaurant groups, franchise organizations, multi-unit operators or similarly complex mid-market businesses.

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

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

• Ability to build credibility with business owners, operators, finance leaders and executive sponsors.

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

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

• Ability to travel up to 30% to meet clients.

Core sales skills at this level

• Builds pipeline through researched, multi-contact outreach into target accounts.

• Ties customer pain to business impact for several stakeholders and builds a customer-specific business case.

• Maps the buying group, multi-threads across roles, and keeps a written deal plan with a mutual timeline.

• Negotiates pricing and terms within guardrails, and supports the forecast with documented deal health.

• Guides other sellers on deals and practices.

Preferred

• Software sales experience selling to the restaurant or hospitality industry, especially accounting, payroll, workforce management or business management software.

• Accounting or restaurant management experience.

• Bachelor’s degree.

What success looks like

• Quota attainment and a qualified pipeline across assigned mid-market accounts.

• Opportunities with validated business impact, and accurate Salesforce and Gong records and forecasts.

• Complex deals advanced and closed with limited reliance on leadership for deal execution.

• Other sellers using the approaches and examples they share.

AI Fluency

• Continuously improves AI workflows and shares successful practices and tips with teammates, for example patterns for account research, stakeholder mapping and ROI business cases.

• Uses approved AI tools, such as Glean, Gong and the AI features in Salesforce, to prepare for multi-stakeholder deals, reviews outputs for accuracy and protects confidential information.

• Uses Gong and deal health prompts to find stakeholder and next-step gaps, and keeps CRM records accurate so AI tools work from good data.

$100,000 - $120,000 a year

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.

This role is hybrid, balancing flexibility with the value of in-person collaboration. To support connection, partnership, and team effectiveness, employees are expected to work onsite each Tuesday and Wednesday.

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.