How to Succeed in Business Without Really Trying at Shenandoah Conservatory: Production Photos and Mini Playbill
Shenandoah Conservatory’s production of How to Succeed in Business Without Really Trying opens October 8, 2026 at the Ohrstrom-Bryant Theatre in Winchester, Virginia, and I had the chance to photograph it for the Conservatory. Below you’ll find the full production photo gallery, a look at director Kevin Covert and his creative team, a shout out to the cast and crew, and a mini playbill you can keep after the curtain comes down.
About the Show
Frank Loesser’s How to Succeed in Business Without Really Trying is the Tony Award and Pulitzer Prize winning musical satire of corporate life. It follows J. Pierrepont Finch, a window washer who climbs the ladder at the World Wide Wicket Company with nothing but ambition, charm, and a little handbook that promises success without the hard work. Along the way he runs into the office party, a scheming nephew, a coffee shortage, and Rosemary, the secretary who sees right through him. The score includes “I Believe in You,” “The Company Way,” “A Secretary Is Not a Toy,” and “Brotherhood of Man.”
Directed by Broadway Veteran Kevin Covert
This production has a special connection to its director. Kevin Covert, director of musical theatre and associate professor of theatre at Shenandoah Conservatory, was part of the cast of the most recent Broadway revival of How to Succeed in Business Without Really Trying, the 2011 production starring Daniel Radcliffe, Darren Criss, and Nick Jonas.
Covert was also in the original Broadway casts of Monty Python’s Spamalot and Memphis, earning a 2010 Fred Astaire Award nomination, and he can be heard on the cast albums of all three shows. He has toured the country with South Pacific, Cats, Grand Hotel, and the 50th anniversary production of Oklahoma!, worked regionally at Goodspeed Musicals, Sacramento Music Circus, Houston TUTS, Kansas City Starlight, and North Shore Music Theatre, and serves as one of Tony Award winner Christopher Gattelli’s associates. He is a BFA Music Theatre graduate of Florida State University.
Shenandoah’s musical theatre program is regarded as one of the top five in the country, and Covert’s students have gone on to Broadway, national tours, and TV and film. Watching someone who lived inside this show on Broadway hand it to the next generation is a big part of what makes this run worth seeing.
The Creative Team
Choreography comes from guest choreographer Michaeljon Slinger, with music direction by Patrick Brady, who also conducts. Scenic design is by R. Eric Stone, costumes by Shelbi Wilkin, wigs by Alexus “Lexi” Cambell, lighting by Andrew Carson, and sound by Nathan Schilz. David Steinmetz is technical director, Kaeleigh Howlett is production stage manager, and John Bonanni is production manager.
Meet the Cast
Giovanni Santoro leads the company as J. Pierrepont Finch, opposite Dalaney Lange as Rosemary. Dylan Stukenberg plays J.B. Biggley, the president of World Wide Wicket, and Aidan Espinosa plays his nephew Bud Frump, Finch’s rival on the way up. Avery Whitacre is Smitty, Kira Sledge is Hedy LaRue, and Phelan Newman is Miss Jones, who gets her big moment in “Brotherhood of Man.” Preston Patrick Kelly doubles as Mr. Twimble and Wally Womper.
The rest of the office is filled out by Evan Smith, Jacob Kim, Aviv Haroz, Matthew Squeri, Blake McCall, Daniel Bosch, Jack Dungan, Olivia Zenetzis, Reagan Kern, Maddie Bobish, Amanda Phillips, and Linnea McKinney, with swings Presley Anderson, JJ McDonough, and Walker Wallace.
Behind the Scenes: The Production Team
None of this happens without the people backstage. Credit to assistant costume designer Isebella Miller, associate lighting designer Charlie Hintz and assistant lighting designer Nathan Shockey (who also share production electrician duties), lead scenic artist Will Freeze-Bell, assistant stage managers Sky Caddell and Taya Burns, A1 and front of house audio engineer Ashlee Round, production assistant Liz Fall, and keyboardists and rehearsal pianists Zoie Foster and Carter Perryman.
Mini Playbill: How to Succeed in Business Without Really Trying
Creative Leadership
Book by Abe Burrows, Jack Weinstock and Willie Gilbert
Music and Lyrics by Frank Loesser
Based on the book by Shepherd Mead
Director: Kevin Covert
Guest Choreographer: Michaeljon Slinger
Music Director and Conductor: Patrick Brady
Scenic Designer: R. Eric Stone
Costume Designer: Shelbi Wilkin
Wig Designer: Alexus “Lexi” Cambell
Lighting Designer: Andrew Carson
Sound Designer: Nathan Schilz
Technical Director: David Steinmetz
Production Stage Manager: Kaeleigh Howlett
Production Manager: John Bonanni
Cast
J. Pierrepont Finch: Giovanni Santoro
J.B. Biggley: Dylan Stukenberg (Dance Captain)
Bud Frump: Aidan Espinosa
Mr. Twimble / Wally Womper: Preston Patrick Kelly
Rosemary: Dalaney Lange
Smitty: Avery Whitacre
Hedy LaRue: Kira Sledge
Miss Jones: Phelan Newman
Mr. Jenkins: Evan Smith
Mr. Peterson: Jacob Kim (Dance Captain)
Mr. Ovington: Aviv Haroz
Mr. Andrews: Matthew Squeri
Mr. Johnson / TV Announcer: Blake McCall
Mr. Tackaberry: Daniel Bosch
Mr. Gatch: Jack Dungan
Miss Krumholtz: Olivia Zenetzis
Lily: Reagan Kern
Kathy / Scrubwoman: Maddie Bobish
Meredith: Amanda Phillips
Mrs. Grabowski / Scrubwoman: Linnea McKinney
Swings: Presley Anderson, JJ McDonough, Walker Wallace
Musical Numbers
Act I: Overture, How to Succeed, Happy to Keep His Dinner Warm, Coffee Break, The Company Way, A Secretary Is Not a Toy, Been a Long Day, Grand Old Ivy, Paris Original, Rosemary
Act II: Entr’acte, Martini Time, “Cinderella, Darling,” Love from a Heart of Gold, I Believe in You, The Company Way (Finale), Brotherhood of Man, Finale
Performance Details
Ohrstrom-Bryant Theatre, Shenandoah Conservatory, 620 Millwood Avenue, Winchester, VA 22601
Thursday, October 8 and Friday, October 9 at 7:30 PM; Saturday, October 10 at 2:30 PM and 7:30 PM; Sunday, October 11 at 2:30 PM
Suggested rating: PG. The production uses theatrical haze and slowly flickering lighting effects.
Presented through special arrangement with Music Theatre International (MTI).
Photographing Theatre at Shenandoah Conservatory
I’ve been photographing productions, concerts, and events for Shenandoah Conservatory for more than a decade, and theatre is still some of my favorite work. A musical like this moves fast. Big ensemble numbers, quick scene changes, and lighting that shifts from cue to cue mean you have to know the show and stay ready, because the moment you want is gone in a second. The goal is always the same: images that show the actors, designers, and crew at their best, that the Conservatory can use to promote its programs, and that families can hold onto for years.
If you run a theatre program, performing arts organization, or school in Northern Virginia, the DMV, or the Shenandoah Valley and need production photography, cast headshots, or full show capture video, I’d love to hear about your next production.
View the Full Production Gallery
The complete set of production photos from How to Succeed in Business Without Really Trying at Shenandoah Conservatory is in the online gallery below. Congratulations to Kevin Covert and the entire company on opening night.