Nick May

The Programme · Toronto · Season 2026

A career in several acts. Theatre. Hospitality. Tech.
Running time: ongoing. No intermission (there is one).

Take your seat ↓

PROMPT BOOK — THE JUNGLE GYM — rev. 2026.10

sm@stage-left ~ $ whoami
nick may
sm@stage-left ~ $ cat roles.txt
producer   director   dramaturg
operator   systems-thinker   host
sm@stage-left ~ $ uptime
since theatre school · 3 careers · 0 regrets
sm@stage-left ~ $ ▍

// SM note: same show, crew’s view. Press B to go back out front.

Who’s Who in the CastNick May

TALENT · HEADSHOT · NICK MAY

NICK MAY (He/Him) is thrilled to be making his debut on this website. A theatre nerd at heart, his career took the jungle-gym route: theatre, then hospitality, then tech. What looked unrelated turned into an unfair advantage.

By day he’s Senior Director, Talent Operations & Technology at Wealthsimple, building people systems that scale and still feel human. Before that he spent the better part of a decade at Shopify, ending as Director of Technical Operations and Chief of Staff to the CTO.

During rare moments of “free time”, he is the creative director/producer of Theatre Topikós, a Toronto queer theatre collective he co-founded in 2014. He’s produced work in three countries, won Best New Play at the Toronto Fringe, and sits on the board of the SummerWorks Performance Festival. He also speaks on panels about AI, work and queer leadership.

He wanted to be a roller coaster tester, but couldn’t break into that industry. Thanks to every mentor along the way.

// SM note: theatre kid → GM → tour director → ops → director. Every role is a rehearsal for the next one.

A Note from the DirectorThe Throughline

Three careers, one job: make the show run, and make everyone in the room feel looked after. Every act taught a piece of it.

Theatre

The show is only as good as the cast and crew behind it.

Run-of-show thinking

Hospitality

Read the room. Anticipate the need. Own the mistake.

Human-first service

Tech

Map it, delete what doesn’t need to exist, then automate.

Systems at scale

“Systems that scale and still feel human.”return "Systems that scale and still feel human.";

Running OrderTonight’s Programme

  1. PrologueThe Creative
  2. Act IThe Hospitality Operator
  3. Entr’acteThe Touring Company
  4. Act IIThe Tech Operator
  5. In RepertoryThe Director / Producer
  6. Special EngagementOn the Bill
  7. IntermissionNotes from the Lobby
  8. Act IIIIn Development
  9. Curtain CallThe Stage Door

PrologueThe Creative

Theatre school, then a lifetime of creating and storytelling

  1. Pre-2007

    Theatre school

    New York City

    Trained for the stage. Learned that every great show runs on a great crew.

  2. 2007

    Home to Toronto

    Stage & screen

    New city, new scene. Stopped waiting for the call and started making the work.

  3. 2014

    Co-founds Theatre Topikós

    With Jess Bryson

    A queer theatre collective, still running in repertory.

Act IThe Hospitality Operator

Restaurants, retail & social enterprise, 2011–2017

  1. 2011–14

    Front of House Manager

    Cardinal Rule, Roncesvalles

    Weekly cocktail specials and a lot of keys.

  2. 2014–16

    General Manager

    Hawthorne Food & Drink

    Social enterprise

    A downtown restaurant backed by United Way Toronto that trained people coming out of homelessness or off social assistance for full-time careers in hospitality.

  3. 2016–17

    Toronto Community Lead

    Mealshare

    Non-profit social enterprise

    Partner restaurants donate a meal to someone in need every time a Mealshare item is ordered. Buy a meal, give a meal.

  4. 2016–17

    General Manager

    Glad Day Bookshop

    The oldest surviving LGBTQ bookstore in North America. Added a café and a bar.

Entr’acte · The Touring Company

International Tour Director

Evolve Tours · 2016–2020

Not quite hospitality, not quite tech: pure operations. Running the show, just with a passport.

Act IIThe Tech Operator

Product, technical & people operations, 2017–now

  1. 2017–19

    Merchant Success

    Shopify

  2. 2019–20

    Product Expansion

    Shopify

  3. 2020–22

    Senior Product Ops Manager → Product Ops Lead

    Shopify

    Product Management Certificate, Product School, 2021.

  4. 2022–23

    Staff Product Operations Manager

    Tonal

  5. 2023–24

    Senior Product Operations Lead

    Shopify

  6. 2024–25

    Director, Technical Operations & Chief of Staff to the CTO

    Shopify

  7. 2026–

    Senior Director, Talent Operations & Technology

    Wealthsimple

    Building People Systems & Ops. Agentic workflows, human welcomes.

Running in Repertory, 2014–nowThe Director / Producer

With Theatre Topikós, Nick produces, directs and does dramaturgy on bold, topical queer work, and co-leads the Toronto Queer Theatre Festival with Mark Keller. Shows have toured from Toronto to Dublin, Edinburgh and Montreal.

Now playingTheatre TopikósBoard of DirectorsSummerWorks Performance Festival

A Special EngagementOn the Bill

Nick speaking on a panel at HR in Tech CrawlNick laughing with fellow panelists on stage

Panels, keynotes, fireside chats. Nick brings a performer’s timing to conversations about AI, work and the people doing it.

  • AI & the future of work
  • People systems & ops
  • Product operations
  • Queer leadership
  • Career pivots
Book Nick for your stage →

Coming up

Previously

Intermission · 15 minutesNotes from the Lobby

Things Nick believes, mostly learned the hard way. Tap one to tear off the stub.

Act IIIIn Development

New work in the rehearsal hall. Not ready for previews yet.

In workshop

Coaching

Certification in progress. Mentors shaped every step of this career, so this is the next one.

What would you try if you knew you couldn’t fail?

In rehearsal

Tuber or Not Tuber

An app about one of Nick’s favourite things: potatoes. Mashed, roasted, hashed, scalloped. Further details are under wraps (in foil).

Tuber or not tuber, that is the question.

Curtain CallThe Stage Door

Want to talk systems, shows or something else entirely? Come round the back and say hi.