Full-Time

Senior Systems Engineer

Level99 Entertainment

Level99 Entertainment

51-200 employees

Open-world, group-challenge entertainment venue

Compensation Overview

$110k - $140k/yr

Boston, MA, USA

Hybrid

Based out of the Greater Boston area; travel to Level99 venues across the country as needed.

Category
DevOps & Infrastructure (2)
,
Required Skills
Computer Networking
Android Development
Linux/Unix

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Requirements
  • Networking, security, network design, Linux, WiFi administration, virtualization, high availability architecture, SD-WAN
  • Ability to work a flexible schedule based on business needs
  • Based out of the Greater Boston area plus travel to Level99 venue locations, as needed
  • Must be available for on-call response to critical infrastructure incidents outside of normal business hours
Responsibilities
  • Network Administration: Design, implement, and maintain the organization’s network infrastructure, ensuring high availability, performance, and scalability across all venues.
  • Network Security: Implement and manage security measures, conduct regular audits, develop security policies, and monitor EDR software to protect the network from unauthorized access and threats.
  • Hardware & Server Management: Manage and stage network and server hardware at venue locations, oversee MDM solutions, coordinate equipment deployments, and perform server administration tasks.
  • Operating Systems: Administer and maintain Windows, MacOS, Android, and Ubuntu operating systems across various devices, troubleshooting and resolving OS-related issues as needed.
  • Vendor Management & Procurement: Establish vendor relationships, evaluate proposals, negotiate contracts, and lead IT procurement processes for hardware, software, and licenses.
Desired Qualifications
  • Relevant certifications (e.g., CISSP, CCNA, CompTIA Network+, CompTIA Security+, MCSA, MDM certification, etc.) are a plus.
  • Experience in construction site environments, low voltage design in architectural drawings, commercial audio systems, and security camera system design and administration is a plus.
  • Willingness to learn quickly in areas that are new.
Level99 Entertainment

Level99 Entertainment

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Level99 runs large entertainment venues in Natick, MA and Providence, RI that feature an open-world game environment with 40+ rooms, each offering physical or mental team challenges for groups of 2-6 players. Guests buy tickets to play the rooms and also purchase food and craft drinks at the on-site Night Shift Beer Hall and Tap Room & Kitchen. The experience blends social problem-solving with dining and beverage offerings in a format aimed at adults, setting it apart with a large, multi-room setup and in-house dining. The company plans to grow through new locations, expanded challenges and amenities, and attracting hundreds of thousands of guests each year.

Company Size

51-200

Company Stage

Late Stage VC

Total Funding

$100M

Headquarters

Natick, Massachusetts

Founded

2021

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Simplify Jobs

Simplify's Take

What believers are saying

  • Disney Springs opening June 29 captures high-footfall tourists, becoming Level99's largest venue with 63 games.
  • Act III Holdings' $2B capital enables rapid East Coast expansion without equity dilution through 2027 openings.
  • Premium Pass add-ons and high-margin food like Wagyu burgers boost ancillary revenue per guest significantly.

What critics are saying

  • King of Prussia 2027 launch shifts 25–35% of Tysons traffic, threatening 8-figure growth runway within 18–24 months.
  • Garden State Plaza 2027 opening erodes 15–25% of Providence and Natick repeat traffic in 12–18 months.
  • Weekend premium tickets reduce repeat frequency by 15–25% compared to Boston's fixed pricing within 6–12 months.

What makes Level99 Entertainment unique

  • Proprietary 63-room open-world game environment with 40+ original art installations at Disney Springs.
  • Veloband RFID system tracks cross-location progress, scores, and leaderboards to drive repeat visits.
  • Blend of physical duels, mental puzzles, and scratch-made Detroit pizza in a 46,800 sq ft adult venue.

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Benefits

Flexible Work Hours

Growth & Insights and Company News

Headcount

6 month growth

14%

1 year growth

14%

2 year growth

14%
Disneygeek
Jun 17th, 2026
Level99 opening June 29th in Disney Springs.

Level99 opening June 29th in Disney Springs. Interactive social gaming venue, Level99, announces opening, on-sale dates for Disney Springs location Lake Buena Vista, Fla., - June 16, 2026 - Level99, the much-anticipated real-world social gaming venue coming to Disney Springs West Side at Walt Disney World Resort, is opening its doors Monday, June 29. Tickets sales for the location will launch Monday, June 22 on Level99.com. Amid the energy and artistic atmosphere of the 46,800-square-foot venue, Players can dodge axes, crack puzzles and outsmart real-world challenges in more than 60 physical and mental life-sized mini-games- the most of any Level99 venue to date. The themed mini-games will be dispersed throughout the first and second floors, with a two-story bar as the centerpiece of the venue. Featuring three ways to play - cooperative Challenge Rooms, competitive Player-vs-Player Duels and an interactive art scavenger hunt - this sprawling playground designed for adults and teens will provide an exciting new entertainment option at Disney Springs. Beyond the games, Players can fuel up with a full selection of scratch food and beverage options offering imaginative flavors focused on making the familiar fantastic using uncompromising commitment to culinary excellence. Menu items will include Level99's award-winning Detroit-style pizza, wagyu burgers and other craveable bites as well as handcrafted cocktails and local beer selections on tap. Players can order via a first-floor kitchen window, at the bar or pick-up beverages on satellite bar carts stationed on the second floor. At check-in, guests will receive a RFID-powered "Veloband," which unlocks access to the Challenges. Players can enjoy all games in the venue for the price of admission, and attempt each game as many times as desired and in any order they like, by tapping their Veloband on an entry screen. Games are active, social and endlessly re-playable, each lasting about 1-4 minutes and designed for 2-6 Players. And the game continues beyond one visit: Level99 saves Players' progress, allowing them to pick up where they left off when they return to any of Level99's locations for their next visit, providing them with the opportunity to climb the leaderboard and earn rewards. The Disney Springs venue will offer the most games of any Level99 location to date with 63 total mini-games and challenges, as well as the company's biggest art installations amongst its more than 40 original pieces of art. "We're thrilled to bring Level99 to Walt Disney World Resort and share it with the millions of visitors who come to Orlando each year," said Level99 Founder and CEO Matt DuPlessie. "As a company founded on innovation and groundbreaking themed entertainment, it is a natural fit to now be at a place built on those very same ideals. We can't wait to welcome our first Players." "We know our guests love the variety of experiences here at Disney Springs and Level99 is a perfect addition to make even more fun memories with friends and family," said Debbie Hart, Vice President, Disney Springs. "We have over 150 ways to shop, dine and play and Level99 is adding to the experience in a big way." Level99 offers Players completely unique challenges unlike anywhere else, as all its games are created, developed and designed by Level99 at its own production facility in Massachusetts. The team continually designs new games that are rotated into the various Level99 venues. A variety of different skills sets and abilities are required across the numerous games, from strength to dexterity to balance to mental aptitude, ensuring there is something for every type of Player. The variety also provides numerous accessible options for Players with mobility limitations, and each game's entry screen provides skill and accessibility information. Signature Level99 games at the Disney Springs location will include: * Axe Run, where Players race across a narrow beam while dodging swinging axes, aiming to hit the finish button as quickly as possible without stepping off course - an adrenaline-pumping test of speed, focus, and agility. * Ninja Swing, where Players test their strength and precision by using ropes to navigate across a series of platforms, each one trickier than the last, earning Stars based on how far the group advances without falling. * Mansion Banquet, where Players step into the role of dinner party planner, racing to solve quirky logic puzzles and perfectly match finicky guests with their ideal seat, entrée and drink before mealtime. Signature Level99 menu items at the Disney Springs location will include: * Loaded Elote Guacamole served with charred corn, queso fresco, lime crema, Tajín, cilantro and tortillas. * Roni, Roni, Roni, a signature Detroit-style pizza made with 24-hour cold fermented dough and baked in a steel pan to get a crispy cheese frico, and topped with Ezzo cupping pepperoni, housemade red sauce, pecorino romano, Calabrian chili and fresh basil. * House Burger, 100% domestic wagyu, sharp white cheddar, caramelized onion, brown butter aioli and brioche. Tickets to Level99 start at $29.99 per Player, providing intervals of 1.5 and 2.5 hours of play. A premium pass add-on will be available, offering expedited check-in and special gifts. To recognize inaugural visitors, the first 500 Players on opening day at Level99 at Disney Springs will receive a commemorative pin upon entry. Level99's operating hours will be: * Monday - Thursday: 11 am to 10 pm * Friday: 11 am to 11 pm * Saturday: 10 am to 11 pm * Sunday: 10 am to 10 pm Located adjacent to the Drawn to Life Cirque du Soleil theater and House of Blues, Level99 adds to the growing list of dining, shopping and entertainment options at Disney Springs, which features more than 150 shops, restaurants and family-friendly leisure activities. The Disney Springs location will be the fourth Level99 location, including sites in Natick, Mass., Providence, R.I., and Tysons, Va. and four other locations under construction in West Hartford, Connecticut, King of Prussia, Pa., Paramus, N.J. and Raleigh, N.C. Guests can follow Level99 on Instagram at @golevel99.

Level99 Entertainment
Jun 9th, 2026
Level99 is coming to Raleigh!

Level99 is coming to Raleigh! June 9, 2026 Level99 is excited to share that Level99 is coming to Raleigh, North Carolina. In 2027, Level99 will open its first North Carolina venue at Crabtree, one of Raleigh's leading shopping, dining, and entertainment destinations. This new location will bring its real-world play and scratch-made dining to Crabtree as part of the property's ongoing redevelopment. The venue will span 40,000 square feet in the former Belk's Men's space and will feature entrances from both inside the mall and the exterior, making it easy for guests to join Level99 for a night out, group celebration, or corporate event. Players can look forward to more than 50 life-sized mini-games, including collaborative Challenge Rooms and competitive Player-vs-Player Duels, plus its Hunt Art featuring local artists. Beyond the games, guests will find scratch-made dining, handcrafted cocktails, craft beer, a 200-seat dining area, a full 24-seat bar, and two private event spaces designed for larger groups. The Crabtree location marks Level99's second collaboration with Macerich and another major step in its continued expansion. In addition to Raleigh, Level99 is also preparing to open new venues at Disney Springs at Walt Disney World Resort this summer, West Hartford, CT later this year, and Garden State Plaza and King of Prussia Mall in 2027! Level99 can't wait to bring Level99 to Raleigh. Stay tuned for more updates as Level99 get closer to opening. Crabtree to Welcome Level99 in 2027, Bringing Interactive Social Gaming and Entertainment to the Triangle Award-winning entertainment concept to open North Carolina's first location at Crabtree RALEIGH, N.C. - Crabtree is expanding its lineup of entertainment offerings with the addition of Level99, an award-winning, real-world gaming concept that blends interactive, social challenges and mini-games with elevated food and beverage offerings under one roof. Crabtree will be home to the concept's first venue in North Carolina, introducing its high-energy experience to the Triangle in 2027. Designed as a sprawling playground for adults, Level99 will feature more than 50 life-sized mini-games including collaborative physical and mental Challenge Rooms and competitive Player-vs-Player Duels built for groups of 2-6 Players to solve, race, and compete together - encouraging teamwork, friendly competition, and repeat play. Players will discover challenges such as axe dodging, puzzle-solving, and an interactive art scavenger hunt featuring works by local artists. Players can move between games, track performance on dynamic leaderboards, and replay challenges to improve scores and climb the ranks. Guests will also enjoy scratch-made dining, handcrafted cocktails, and craft beer amongst the venue's 200-seat dining area, full 24-seat bar, and two private event spaces built for large groups. "Level99 represents the kind of innovative, experience-driven concept we're bringing to elevate and transform Crabtree as we continue to invest in the property's future," said Eric Bunyan, Senior Vice President, Leasing, Macerich. "Raleigh and the Research Triangle's momentum, growth, and vibrant community make it the ideal home for this one-of-a-kind destination. We look forward to welcoming Level99 as Crabtree becomes its first venue in North Carolina, marking an exciting new chapter for the property." Level99 will span 40,000 square feet in the former Belk's Men's space as part of the ongoing redevelopment of Crabtree. The venue will feature entrances from both inside the mall and the exterior, creating seamless access for guests visiting Crabtree's expanding list of shopping, dining, and entertainment experiences. "Crabtree is exactly the kind of vibrant, high-traffic destination where Level99 can thrive," said Matt DuPlessie, Founder and CEO of Level99. "We are excited to partner with Macerich again following our successful opening in Tysons Corner and open our first North Carolina venue together in Raleigh at Crabtree. Crabtree's redevelopment makes this an ideal moment to bring our real-world play and scratch made dining to the Triangle, and we cannot wait for the community to see what we are all about." The Crabtree location marks Level99's second collaboration with Macerich as the brand accelerates its strategic expansion into major markets. Level99 will also open at other super regional centers along the East Coast and Southeast, including King of Prussia mall and Garden State Plaza in 2027 and Disney Springs at Walt Disney World Resort this summer. About Crabtree With nearly 200 stores and dozens of restaurants, Crabtree is home to leading national brands including Apple, Banana Republic, Belk, Brahmin, Brooks Brothers, Chubbies, Coach, H&M, Hollister, LEGO, lululemon, Macy's, Michael Kors, TAG Heuer, and Tommy Bahama, among many others. Dining destinations include Kanki Japanese House of Steaks & Sushi, P.F. Chang's China Bistro, The Cheesecake Factory, and Seasons 52. Recent additions include Escapology, with Level99, Pop Mart, JD Sports, DICK'S House of Sport, and Five Guys coming soon. The largest mall in North Carolina's high-growth Research Triangle area at 1,346,658 square feet, Crabtree today features nearly 200 total tenants and is anchored by Belk and Macy's and has over 8.7 million annual visitors. For more information, please visit www.ShopCrabtree.com. About Level99 Level99 is a sprawling entertainment venue, offering proprietary, real-world physical and mental interactive challenges and life-sized mini games. Founded by location-based entertainment innovator Matt DuPlessie, the company is headquartered in Natick, Mass., with a second location in Providence, R.I., third in Tysons, Va., and five more under construction in Lake Buena Vista, Fla., West Hartford, Conn., Paramus, N.J., King of Prussia, Pa, and Raleigh, NC. Level99 is backed by Act III Holdings. More information is available at www.level99.com. About Act III Holdings Act III Holdings is a $2 billion evergreen investment vehicle formed by Ron Shaich, founder and former Chair and Chief Executive Officer of Panera Bread and current Chairman and lead investor of Cava. Act III holds significant investments and strategic advisory roles in Tatte Bakery, Life Alive Organic Café, Honest Greens Barcelona, and Level99, supporting the growth of tomorrow's market-leading restaurant and entertainment companies. Act III invests in emerging restaurants, entertainment, and technology brands, and helps them build a dominant position in powerful categories within their respective industries. Act III also partners with public companies to provide strategic advice and capital. Shaich and his team are known for their long-standing track record of building competitive advantage by successfully fostering innovation and thoughtfully scaling private and public companies to positions of dominance. For more information, visit www.act3holdings.com.

NJBIZ
Mar 17th, 2026
Level99 interactive gaming, dining concept coming to NJ (photos).

Level99 interactive gaming, dining concept coming to NJ (photos). A social entertainment concept that blends interactive challenges with food and drinks is coming to New Jersey. Billed as a sprawling adult playground, Level99 is scheduled to open next year at Westfield Garden State Plaza in Paramus. In addition to marking its first in-state location, it's also the first site to open in partnership with multinational CRE firm Unibail-Rodamco-Westfield (URW). Players will have the opportunity to move through dozens of short, immersive challenge rooms at the 38,000-square-foot space. The areas are designed to play solo, or with friends. A full-service bar and restaurant will complement the gaming experience. Level99 launched its first location four years ago in Massachusetts. Since then, it has expanded with additional venues in Rhode Island and Virginia. The company also has launches planned in Florida, Connecticut and Pennsylvania. At Westfield Garden State Plaza, Level99 takes space previously occupied by bankrupt fashion retailer Forever 21, according to a spokesperson. 'More ways to play' at GSP. Level99 founder and CEO Matt DuPlessie said, "We're thrilled to introduce Level99 to the New York-New Jersey metropolitan area in partnership with Westfield." "Garden State Plaza represents exactly the kind of experience-driven destination where our brand thrives. This location will showcase some of our most ambitious design work to date - delivering competitive, social gameplay, purpose-built for adults," he said. Garden State Plaza represents exactly the kind of experience-driven destination where its brand thrives. - Matt DuPlessie, founder and CEO, Level99 Ron Shaich also backs the brand. The Essex County native is often credited for pioneering the $100 billion-plus fast casual dining segment. His background includes serving as founder and CEO of Au Bon Pain and Panera Bread. Other concepts in his Act III Holdings' $1.5 billion evergreen investment vehicle include Cava, Tatte Bakery and Life Alive Organic Café. Westfield Garden State Plaza Vice President of Center Management Sue Newsom said, "We're expanding our entertainment lineup to give guests of all ages more ways to play, connect, and make memories at GSP." Entertainment venues at the busy shopping center also include AMC Theatres, Dopamine Land and Power Up Arena.

FREEDOMX
Oct 27th, 2025
King of Prussia Mall Unveils Plans for Expansive Real-Life Gaming Venue with Dining and Drinks

King of Prussia Mall unveils plans for expansive real-life gaming venue with dining and drinks. King of Prussia Mall is set to welcome Level99, an innovative experiential retail concept, in 2027. This sprawling "adult playground" will feature 50 life-size mini-games, a full-service restaurant, and a bar offering local craft beers, marking Level99's debut in the Philadelphia market. Key takeaways. * Level99, a Massachusetts-based company, will open a 46,000-square-foot venue at King of Prussia Mall in 2027. * The venue will offer 50 "life-size mini games" designed for adults, alongside a restaurant and bar. * This expansion is part of a broader trend of experiential retail transforming malls nationwide. A new era of entertainment. Massachusetts-based Level99 has announced its intention to open its next "sprawling adult playground" at the King of Prussia Mall in 2027. This marks the company's first venture into the Philadelphia market. The expansive 46,000-square-foot venue is designed to be an immersive social-gaming experience, featuring 50 "life-size mini games" specifically geared towards adults. Complementing the gaming attractions, the venue will also house a full-service restaurant and bar, complete with a selection of local craft beers. Matthew DuPlessie, founder and CEO of Level99, stated, "Level99 goes beyond your conventional entertainment venue - it's a place to play, explore, and actively connect." The new location will occupy the ground floor of the former JCPenney building, which has been vacant since 2017. This strategic placement positions Level99 across from the highly anticipated Netflix House, an immersive experience set to open in November in the former Lord & Taylor space. Elevating the mall experience. Mark Silvestri, president of development for mall owner Simon Property Group, expressed enthusiasm for the addition, saying, "We're thrilled to welcome Level99 to King of Prussia, further elevating our commitment to delivering dynamic, experience-driven destinations. This innovative concept brings a new layer of interactive entertainment to King of Prussia and is a perfect complement to our growing lineup of immersive offerings." The arrival of Level99 aligns with a national trend of experiential retail, which is helping malls adapt to the rise of online shopping by filling vacant spaces with unique attractions and drawing in customers seeking more than just traditional retail. Regional experiential retail growth. King of Prussia Mall is not alone in embracing experiential concepts. In the Philadelphia region, Cherry Hill Mall is preparing to open a 120,000-square-foot Dick's House of Sport next year, featuring amenities like a climbing wall and golf simulators. Moorestown Mall is also set to introduce a large entertainment center with axe-throwing and go-karts in a former department store space. In Center City, the Fashion District is exploring additional experiential retail options following the success of venues like Puttshack mini golf and F1 Arcade. In addition to the upcoming Netflix House, King of Prussia Mall recently welcomed Eataly, a 21,000-square-foot Italian marketplace and wine shop. Level99 itself has been expanding rapidly, with its flagship location opening in 2021 at Natick Mall near Boston, followed by openings in Providence, R.I., and Tysons, Va. Future locations are planned for Hartford, Conn., and Disney Springs in Orlando. Pricing at existing Level99 locations typically starts at $29.99 per person for a two-hour play session, with potential increases for weekends, holidays, and extended playtimes. The company's expansion is backed by Act III Holdings, a private-equity firm that has committed $50 million to support Level99's growth into new markets, including Philadelphia.

FinSMEs
Sep 10th, 2025
Level99 Raises $50M in Growth Equity Funding

Level99, a Natick, MA-based company which specializes in active, social entertainment featuring 50+ real-world, physical and mental challenges, raised $50M in Growth Equity funding.