Mid-Market Account Executive

Olo; Oregon; Hybrid; USD 84,000 - 121,000; Full time

Benefits offered by this job

20 days PTO

10 sick days

11 holidays

Year-end closure

Health, dental, vision

401k match

Remote-office stipend

Parental leave

Volunteer time off

Gift matching

Job summary

Olo is seeking a Mid-Market Account Executive to drive full sales cycles with restaurant brands across 5–49 locations. You will prospect, demo, propose, and close deals, building a strong pipeline and engaging stakeholders across the organization.

Remote-friendly, US-based, the role emphasizes SaaS, payment solutions, and hospitality tech expertise, with compensation ranging from $84,000 to $120,500 annually plus incentives.

Qualifications

• 5+ years of sales experience in B2B SaaS, payments, or hospitality tech.
• Ability to prospect daily and build pipeline independently.
• Strong discovery skills and a structured sales process.
• Experience selling platform-based products and communicating with C-level executives.

Responsibilities

• Own the full sales cycle—from prospecting to close.
• Build and manage a healthy pipeline through outbound prospecting and partnerships.
• Deliver product demonstrations and tailored proposals to prospects.
• Coordinate meetings and craft timely follow-up materials.
• Partner with Deployment and Customer Success to ensure successful launches.
• Maintain pipeline to meet monthly/quarterly revenue and new client goals.

Skills

Sales experience

Closing deals

Prospecting

CRM (Salesforce)

Product demos

Cross-functional collaboration

Tools

Salesforce

Excel

Job description

Olo is a leading SaaS platform accelerating digital transformation in the restaurant industry, by helping customers deliver more personalized and profitable guest experiences. As a result, our digital ordering, payment, and guest engagement solutions enable brands to do more with less and make every guest feel like a regular.We are looking for a motivated Mid-Market Account Executive to add to our industry-leading GTM team. In this role, you will develop relationships with prospective brands ready to scale their digital potential. The ideal candidate will possess technical aptitude, sharp project management skills, and comfort selling into all levels of an organization. Sound like you? Read on.

Olo's industry-leading online ordering platform has changed the restaurant landscape, helping many of our customers achieve 40%+ digital sales. You will be helping new logo brands move beyond fragmented tech by adopting an integrated platform for ordering, payments, and guest engagement.

This is an exciting opportunity to join a growing group of Account Executives within Olo's Mid-Market Sales team, focused on restaurant brands with between 5 and 49 locations . You will report to the Senior Manager, Mid-Market Sales, and can work remotely from anywhere in the U.S. or at Olo's headquarters in NYC.

How You'll Make An Impact

• Own the full sales cycle — from self-sourced prospecting and territory prioritization through discovery, demo, proposal, and close.
• Build and manage a healthy pipeline through outbound prospecting, referrals, industry events, and partner channels.
• Drive awareness of Olo products and services to an assigned "Book of Business" and book meetings to explore sales opportunities.
• Deliver a unified vision of Olo's Order, Pay, and Engage solutions, and present a recommended proposal for each prospect based on a thorough understanding of their business model, technology stack, and growth plans.
• Build and manage key stakeholders and "champions" through multi-threading within target organizations.
• Conduct high-impact product demonstrations (video conference or face-to-face) showcasing how Olo solutions help brands deliver personalized hospitality at scale while driving incremental revenue.
• Coordinate customer meetings and deliver timely recaps with associated follow-up materials.
• Manage the full sales cycle, from initial discovery and qualifying competitive threats to final contract negotiations.
• Partner with the Deployment and Customer Success teams to ensure seamless program launches that meet client expectations.
• Maintain a consistent pipeline to meet and exceed monthly/quarterly revenue and new client acquisition goals.

What Will Set You Up For Success

• 5+ years of sales experience, with 3+ years in a closing role (B2B SaaS, payment solutions, or hospitality tech preferred).
• You prospect as a daily habit to build pipeline independently, without solely relying on inbound or marketing leads.
• You understand the whitespace of each account in your book and perform outbound prospecting to brands with relevant messaging to create the necessary pipeline coverage.
• You conduct excellent discovery and adopt a structure to determine whether to continue the sales conversation.
• You demonstrate an ability to identify, build, and manage key stakeholders throughout the process.
• You adopt a standard sales process or methodology, clearly articulating the specific actions that each role is responsible for within the process.
• You arrive for each key conversation with an agenda and set questions, and follow up with thoughtful discussion points and next steps.
• You have experience selling platform-based products and are comfortable getting "into the weeds" with prospects.
• Able to communicate with multiple internal departments about client feedback and work cross-functionally to solve problems.
• You are proficient in demonstrating complex platforms and highly skilled in CRM (Salesforce), Excel, and data analytics tools.
• Exceptional presentation skills and the ability to simplify complex technical concepts for C-level or founder-level decision makers.
• You are experienced with deciphering legal contracts and navigating the nuances of multi-year SaaS agreements.
• Comfortable managing a high volume of deals simultaneously in a fast-paced, remote-friendly environment.
• You're client-focused, motivated, and have prior results to prove it.
• Experience selling to the hospitality/restaurant industry, payment solutions and/or SaaS-based products is a plus.
• Experience building trust with "Founder-led" brands, where decision-making is often highly personal and less bureaucratic than enterprise environments, is preferred.
• Ability to consult brands specifically on the "inflection point" of scaling from 5 to 49 locations, positioning Olo as the foundation for growth is a plus.
• Preferred: skill in tailoring customized ROI models that quantify the "cost of inaction" regarding fragmented tech stacks.
• Deep knowledge of the hospitality tech ecosystem to proactively differentiate Olo against legacy POS providers and niche ordering and guest engagement apps.
• The social intelligence to manage the varying priorities of a brand leader, an operations lead, a head of technology, a finance lead, and a head of marketing simultaneously is a plus.

About Olo

Olo is a leading restaurant technology provider with ordering, payment, and guest engagement solutions that help brands increase orders, streamline operations, and improve the guest experience. Each day, Olo processes millions of orders on its open SaaS platform, gathering the right data from each touchpoint into a single source—so restaurants can better understand and better serve every guest on every channel, every time. Over 800 restaurant brands trust Olo and its network of more than 400 integration partners to innovate on behalf of the restaurant community, accelerating technology's positive impact and creating a world where every restaurant guest feels like a regular.

We’re remote-friendly. Since 2015, we have been evolving our culture to continue to support a more distributed workforce and now over 75% of our team works remotely across the U.S. If you're in the New York City area, you can choose to work remotely or from Olo's headquarters.

We offer great benefits, such as 20 days of paid time off, 10 sick days, 11 holidays, plus year-end closure, health, dental, and vision coverage for yourself and your family, a 401k match, remote-office stipend, a generous parental leave plan, volunteer time off, gift matching policy, and more!

Our best estimate of the compensation range for this opportunity is $84,000 - $120,500 annually, depending on the experience you bring and your location. This role is also eligible for incentive compensation. We look forward to discussing your salary expectations and our full total rewards offerings throughout the interview process.

At Olo, we believe bringing together people with varied experiences and viewpoints leads to better results. Don't check every box in the job description? Research shows many qualified candidates hold back from applying unless they meet all listed requirements. We’re committed to creating a genuine workplace where everyone can contribute their best work—this improves our decision-making and helps us better serve our communities. If you’re enthusiastic about this role but your background doesn’t perfectly align with every qualification, you might be exactly the right fit for this or other positions.

All applicants receive consideration for employment.

We do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, pregnancy, age, marital status, veteran status, or disability status.

California Residents: CCPA notice