--- title: Careers on the night shift | Sleepy Hollow Security description: The best place to work after dark. Seven centuries of experience, four degrees of visibility, and benefits you will have questions about. Open roles for every era and form. --- [Skip to main content](https://www.sleepyhollowsecurity.com/careers#main-content) LICENSED · BONDED · DECEASEDDUSK TO DAWN · SEVEN NIGHTS A WEEK ★ NOW HAUNTING OFFICE PARKS ★ ★ THE INTERCOM POSSESSION IS HERE ★ ★ SIGN MY GUESTBOOK ★ ★ NO BRIDGES ★★ NOW HAUNTING OFFICE PARKS ★ ★ THE INTERCOM POSSESSION IS HERE ★ ★ SIGN MY GUESTBOOK ★ ★ NO BRIDGES ★ Pause [![](https://www.sleepyhollowsecurity.com/hubfs/raw_assets/public/sleepy-hollow-security/images/shield-animated.svg) Sleepy Hollow Security](https://www.sleepyhollowsecurity.com/?hsLang=en) Menu - [Services](https://www.sleepyhollowsecurity.com/services?hsLang=en) - [After-Hours Haunting](https://www.sleepyhollowsecurity.com/after-hours-haunting?hsLang=en) - [Small-Premises Haunting](https://www.sleepyhollowsecurity.com/small-premises-haunting?hsLang=en) - [Wide-Area Haunting](https://www.sleepyhollowsecurity.com/wide-area-haunting?hsLang=en) - [All services and prices](https://www.sleepyhollowsecurity.com/services?hsLang=en) - [How it works](https://www.sleepyhollowsecurity.com/how-the-haunt-works?hsLang=en) - [About](https://www.sleepyhollowsecurity.com/about?hsLang=en) - [Careers](https://www.sleepyhollowsecurity.com/careers?hsLang=en) - [The Gazette](https://www.sleepyhollowsecurity.com/blog?hsLang=en) - [Request a ride-through](https://www.sleepyhollowsecurity.com/book-a-ride-through?hsLang=en) Careers on the night shift # The best place to work after dark. Seven centuries of experience, four degrees of visibility, and one employer who has never asked anyone to cross a bridge. We hire from every era, every form, and every shift. Applications are read at dusk. ![Abigail Crane, Director of Operations](https://www.sleepyhollowsecurity.com/hubfs/Abigail%20Crane%2c%20Director%20of%20Operations.jpeg) Hiring ## Think you can haunt? Applications are read at dusk. [Apply below ▸](https://www.sleepyhollowsecurity.com/careers#apply) **7 centuries**represented on the payroll **4 degrees**of visibility welcome, including invisible **11 openings**right now, none of them ordinary **0 bridges**you will ever be asked to cross Why they love it here ## Ask the night shift People who have worked everywhere, in every era, tell us this is the one. Their words, lightly edited for the living. > I was a draft in a break room for a long time. Now I am a certified cold spot with a temperature log, a crossword partner, and a sweater allowance. ![](https://www.sleepyhollowsecurity.com/hubfs/Cold%20Spot%20Dave%2c%20IT%20%26%20Monitoring.jpeg) **Cold Spot Dave**IT and Monitoring > At my last posting nobody read the labels. Here the finance director leaves me a fresh pen every Friday. I have never felt more seen, which for a skeleton is a technicality. ![](https://www.sleepyhollowsecurity.com/hubfs/Rattles%2c%20Compliance%20%26%20Audits.jpeg) **Rattles**Compliance and Audits > I have received guests for two centuries. This is the first employer to ask how I prefer to be addressed. It is the Gray Lady, and they put it on the door. ![](https://www.sleepyhollowsecurity.com/hubfs/The%20Gray%20Lady%2c%20Front%20Desk%20%26%20Client%20Relations%20Painting.jpeg) **The Gray Lady**Front Desk and Client Relations, since 1823 > The cleaning crew orders me a pizza every quarter. I cannot eat it. I have never felt so included. ![](https://www.sleepyhollowsecurity.com/hubfs/The%20Night%20Shift%20Chaperone.jpeg) **The Night Shift Chaperone**Office Parks > I have told the lantern story forty-one times. Management has not asked me to stop, and the audience has not left. T **The Old Sea Captain**Coastal and Marina Properties > Coverage of the far side comes with housing. It is a bridge. I have never been so happy with a commute. ![](https://www.sleepyhollowsecurity.com/hubfs/The%20Bridge%20Liaison.jpeg) **The Bridge Liaison**Properties Across the Water ## Open roles: new this season Six new openings, each one real and none of them ordinary. ### Frustratingly Present Black Cat *Perimeter & Rapid Annoyance* Be underfoot at all times. Sit on the one document, keyboard, or phone charger someone needs, cross every path at the least convenient moment, and knock exactly one object off a shelf per shift. Intruders who meet you blame their luck and go home. Must be unbothered. Must be in the way. Compensation: tuna, in kind, and a sunny windowsill that is, strictly speaking, not ours. ### Vampire (Mild Glamour Only) *Customer Calm & Door Persuasion* We need someone who can talk a guard dog down and persuade a door it is already open. Your glamour lasts about forty seconds and works only on the already tired, which suits an after-hours business. Must be able to enter without an invitation, since we do not take residential accounts. Garlic allergy must be disclosed. Compensation: night differential and a standing blood-orange juice order. ### Pegasus *Mythical Haunt, Aerial Patrol* Cover rooftops, parking structures, and loading docks from above, and give the Horseman a view of the whole property in one pass. Must be comfortable with airspace, wind, and being photographed by confused pilots. Unlike some of our staff, you may fly over bridges. We ask that you not describe how it feels. Compensation: premium oats and an honorary hangar. ### Invisible Skateboarder *Parking Lots & Loading Docks* Be heard, never seen. You will kickflip near people who should not be there and ollie the loading dock curb at 3 a.m. Must remain invisible at all times, including in the staff photograph. Helmet optional; we have confirmed it makes no difference. Compensation: one smooth stretch of concrete and a new set of wheels every quarter. ### Old Sea Captain Who Has Seen Things *Coastal & Marina Properties* Sit at the end of the dock. You have seen things you cannot explain, but you will try, slowly and captivatingly, to anyone who wanders by. Our best results come from intruders who stay until sunrise to hear how it ends. Must have strong views about knots and at least one unexplained incident aboard a vessel. Compensation: a pipe, a dry berth, and a rum-adjacent beverage. ### Monster Under the Bed (six openings) *Lodging Vacancy Coverage* Hotels, inns, and vacation rentals sit empty between guests, and an empty room needs someone beneath the bed. Stay put while the room is occupied. Emerge only when the room is vacant and something is amiss. Must respect every Do Not Disturb sign. Minimum clearance: two inches. Compensation: one stray sock per night, your choice of sock. ## Standing roles ### Poltergeist *Wide-Area Operations* Rattle shopping carts across parking lots at 3 a.m., run the Intercom Possession, and cover your assigned department. Writes a short report each morning. Slamming doors is not a report. ### Banshee *Customer Alerts* Wail when, and only when, a real problem occurs. Adjust your volume for the setting: a pharmacy gets a firm, clear note, and a school a gentler one. A banshee who cries wolf gets ignored. ### Hall Monitor Ghost *Schools* Patrol the halls after dark and politely ask anyone who should not be there for a hall pass. Most adults freeze on the spot. ### Night Shift Chaperone *Office Parks* Haunt alongside the cleaning crews and keep an eye on the doors they prop open. Never the star of the night shift: the crew is. ### Bridge Liaison (Troll) *Properties Across the Water* Cover the properties our founder cannot reach, including parking structures across the creek and office buildings joined by skywalks. Must have a deep and lasting relationship with at least one bridge. Housing included. It is a bridge. Benefits ## What you get Everyone is eligible from the first night. The good ones are real. The strange ones are also real. We have chosen not to explain them. - **You write the playbook**Every service on this website was invented by an employee. Pitch yours at the monthly review. If the Proprietor says no, he has to put it in writing, and he never has. - **Your name on your work**Credit goes where it belongs. There is a cold spot on Main Street that everyone calls Dave’s, and Dave likes that. - **Choose your nights**Work as many nights as suits you and swap with a colleague whenever you like. Nobody has ever been asked what they did with their night off. - **Medical, dental, and vision**Full coverage from your first night. Dental includes fangs (cleaning only). Vision includes second sight. - **401(k) with a full match**We match 100 percent, and you are vested after 250 years of service. The Proprietor is the only person who qualifies, and he is delighted. - **Paid daylight**You are paid for every hour you spend dormant between dawn and dusk. No sunlight is provided, and none is required. - **Time off that does not expire**Thirty days a year, accrued even while dormant, rolling over for up to three centuries. - **A training budget**$1,500 a year toward any course, apprenticeship, or certification, including subjects not taught since 1850. - **A real career path**Banshees become senior banshees become heads of Intrusion Alerts. Most of our directors started on the night shift. - **Everything you need, provided**Chains, sheets, lanterns, and fog are issued and maintained. Bring yourself, or what remains. - **Commuter benefits**Pre-tax transit for ferries, ghost trains, ley lines, and one horse. Bridge tolls are reimbursed and have never been claimed. - **Wellness stipend**$300 a year toward chain oil, ectoplasm filters, or lantern wicks. - **A workplace for everyone**Mirror-free restrooms, dim lighting, and fog on request. Accommodations are a phone call away, and the phone rings once. - **Life insurance**Coverage continues after death at no additional cost, which has made the paperwork unusually simple. - **Parental leave**Twelve weeks, fully paid. Nobody has asked. The form is in the good drawer. - **Free coffee**Kept warm all night. No one can drink it. Everyone is grateful. Sleepy Hollow Security is an equal opportunity employer. We welcome applicants of every era, form, and degree of visibility, regardless of origin, species, or how recently they died. Reasonable accommodations include dimmer lighting, thicker fog, and a bridge-free commute. ## How to apply Fill in the form below. Pick your role, tell us whether you can be seen, and tell us how you feel about bridges. Applicants who do not cross bridges are asked to say so, and we will not ask why. Applicants who cannot be seen are asked to describe themselves anyway. Applications are read at dusk. 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Left immediately. 10/10." *– Anonymous Burglar* "Great service, very cold." *– Main St. Pharmacy* "Please stop the footsteps in Aisle 9." *– Store Manager (we will not)* ![Sleepy Hollow Security mark](https://www.sleepyhollowsecurity.com/hubfs/raw_assets/public/sleepy-hollow-security/images/shield-animated.svg) ## Unique visitors this month · October 2026 001430 POWERED BY ECTOPLASM VALID HTML 4.01 (PROBABLY) HAUNTED WEBRING ◄ ► Best viewed at dusk in Netscape Navigator 4.0 at 800x600 · Last updated by Ezekiel, Webmaster · Bridges not crossed · © 2026 ---