Mid-Market Account Executive

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.

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.

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.