How Lindsey Schidlovsky Built a Sales Leadership Career at Toast

When it comes to the future of sales, Lindsey Schidlovsky sees more opportunity than ever. Schidlovsky is the area vice president of restaurant point of sale and management software company Toast, where she coaches and develops sales talent while leading the go-to-market strategy for the region that stretches from Maryland, D.C., Delaware and Virginia, down to Texas.

“Right now, I am extremely excited about how AI can help our sales team work smarter by freeing up our reps from time spent in data so they can focus more on the customer and their teams,” Schidlovsky said. “It also opens the door to richer insights across our organization, helping us better understand operator needs and market dynamics, and ultimately how we support restaurants at scale.”

Schidlovsky is well-poised to help Toast’s sales teams conquer this new technological frontier. With over 20 years of experience in everything from public relations to software sales, Schidlovsky has witnessed the restaurant technology’s transformation firsthand — and she doesn’t shy away from a challenge. She helped her team successfully weather the COVID-19 pandemic, and in 2024, earned “Regional Vice President of The Year” after bringing in the highest live revenue company-wide, paving the way to her current area vice president role. 

Built In caught up with Schidlovsky to hear more about her career journey, the obstacles she has overcome and her advice for aspiring sales professionals.

What an Area Vice President of Sales at Toast Does

I look at my responsibilities through two lenses: people leadership and go-to-market strategy. People leadership means coaching and developing talent and ensuring our teams are fully equipped to hit their revenue targets for booked and live business. Go-to-market strategy is designing leadership development pipelines, running district manager enablement and deploying new product releases. 

One of the most rewarding parts of my strategic work is finding new technology that actually makes our sales team's job easier. Right now, I am extremely excited about how AI can help our sales team work smarter by freeing up our reps from time spent in data so they can focus more on the customer and their teams. It also opens the door to richer insights across our organization, helping us better understand operator needs and market dynamics, and ultimately how we support restaurants at scale. 

“One of the most rewarding parts of my strategic work is finding new technology that actually makes our sales team's job easier.”

What has shifted drastically over time — especially in the last six to eight months — is how technology plays a part in achieving those leadership goals. Historically, leadership required spending a substantial amount of time digging through raw data to isolate performance trends before going into the field to verify them. 

Today, data-processing tools and AI handle that sorting for me. These tools help surface the patterns and context behind the numbers, unlocking massive leadership capacity. Instead of being stuck behind a screen analyzing spreadsheets, I am out in the field shadowing live calls, conducting face-to-face coaching sessions and actively supporting my team. My goal has evolved from just managing revenue metrics to actively experimenting with innovative tools that remove friction for our reps, allowing them to focus entirely on what they love to do: selling and consulting with customers.

How Lindsey Schidlovsky Built Her Sales Career at Toast

My journey in hospitality started in college, where I worked as a waitress. After graduating, I joined a PR agency in New York City, managing campaigns for restaurant, wine and spirits brands — an experience that cemented my passion for the industry. Over the next 20 years, my career evolved from PR into beverage sales and then software sales. 

A turning point came when my husband and I moved to Australia so I could lead a mid-market enterprise sales team. While I missed the fast pace of small- and medium-size business, I couldn't ignore how far ahead Australia was in restaurant technology — every restaurant already had pay-at-the-table handheld terminals, something the U.S. was still catching up on. Moving back to the states, I researched companies bringing that same efficiency here and discovered Toast had just launched its handheld device. I knew it would transform the U.S. restaurant industry.

“Moving back to the states, I researched companies bringing that same efficiency here and discovered Toast had just launched their handheld device. I knew it would transform the U.S. restaurant industry.”

I joined Toast seven years ago as a district manager based in Rhode Island, managing New England; our former CEO would regularly join me on field sales calls. After two and a half years, I was promoted to regional vice president of the Midwest, and later, senior regional vice president. In 2024, I earned Regional Vice President of The Year after bringing in the highest live revenue company-wide — paving the way to my area vice president role. 

I didn’t necessarily foresee this exact title, but I have always known that coaching, mentoring and developing people are what give me the most professional energy. My goal has always been to lead and empower large, high-performing sales organizations. 

How Toast’s Sales Team Adapted During the COVID-19 Pandemic

Without a doubt, leading my sales team through the onset of COVID-19 was the most challenging period of my career. Overnight, our field-based team had to transition to fully remote work. At the same time, our core mission shifted — standard selling wasn't meeting the crisis of the moment for an industry fighting for survival. 

We pivoted immediately to launch an emergency initiative called Toast Now, offering our digital ordering tools to restaurants for free so they could keep their doors open. My primary job shifted from managing standard KPIs to becoming the "calm amongst the storm" for my reps and our restaurant partners.

The silver lining of that intense setback was watching it permanently redefine the digital landscape of hospitality. Before the pandemic, a digital storefront and online ordering were viewed by many traditional operators as optional. 

Today, it’s table stakes. That crisis taught me that the best way to address a massive setback is to lean directly into customer empathy, adapt your product delivery to meet the immediate market need and anchor your team with clear, transparent communication. 

“The best way to address a massive setback is to lean directly into customer empathy, adapt your product delivery to meet the immediate market need and anchor your team with clear, transparent communication.”

Lindsey Schidlovsky’s Advice for Building a Sales Career

The most impactful piece of professional advice I ever received came from my previous leader, who always told me: "Bring your whole self to work." 

Early in my career, I didn’t fully grasp what that meant. Today, it is the core piece of advice I pass down to my own managers and incoming sales talent. Sales can be an intimidating, highly competitive environment, and it's easy for younger professionals to feel like they need to fit into a rigid corporate mold to add value. But the truth is, Toast’s greatest asset is the diversity of backgrounds, perspectives and unique life experiences our people hold. 

What makes you uniquely valuable to a sales team — and to the restaurant operators you partner with — is you. Sharing your genuine story, making authentic personal connections and bringing your distinct perspective to the table is what builds trust. 

For candidates looking to join us, I always share that while our unmatched product innovation and fast-paced market growth are what initially attracted me to Toast seven years ago, the deeply supportive, authentic culture and the incredible people are what keep me here.

Frequently Asked Questions

Note: This article was co-written with Lindsey Schidlovsky of Toast.