Assistant Program Lead

Role: Assistant Program Lead

Role Specifics

Job type: Part Time (4 days/week - 2 days on-site in Vaughan, ON; 2 days remote or in the field)

Category: Hybrid (On-site + Remote/Field)

About PlainStripes

We are a growing organization focused on creating tools, content, and programs that help people work smarter and live better.

Our work spans educational trainings, data analytics, finance, organizational tools and planners, and community empowerment.

We've worked on projects with notable clients like Juniper and Dolby, and we're now building out new programs and offerings that combine structure, creativity, and impact.

About the Role

PlainStripes is looking for an Assistant Program Lead who will also serve as Head Stylist and Content Creator for a new program targeted at empowering women in the GTA area through fashion and career. This is a creative leadership role for someone who thrives at the intersection of program design, styling, content development, and community engagement.

You'll lead a new community-centered program focused on style, self-expression, and empowerment for women of different age groups. You'll be responsible for everything including, recruiting volunteers, designing the program theme, curating thrifted outfits, creating content that tells powerful visual stories and executing on site program events.

This is not a typical 9 to 5 as you'll have freedom to shape the direction of the program and will be rewarded for your initiative, originality, and ability to bring ideas to life. If you love building things from the ground up, working closely with people, and creating beauty and meaning in your work, this might be the right fit.

What You'll Do

• Lead the vision and day-to-day management of a grassroots women's empowerment program.

• Choose and evolve a theme for the program that aligns with your purpose and style philosophy.

• Thrift, source, and curate outfits for styling sessions and content.

Create and publish visual and written content - including short videos, photo stories, and lookbooks.

• Host in-person and virtual events, workshops, and styling sessions.

Recruit, train, and coordinate volunteers.

• Build and engage a warm, inclusive community, both online and in-person.

Collaborate with the CEO and creative team to shape messaging and program structure.

Skills Required

• Styling & Curation (30%) - Strong visual and aesthetic sense; ability to build cohesive looks with thrifted or sourced pieces.

• Program Design (20%) – Ability to conceptualize and structure engaging programs and sessions that align with the theme and community needs.

• Program Management (20%) - Ability to lead a grassroots program with a budget report, volunteers, vendors, sessions, and ongoing development.

• Content Creation (10%) - Experience with visuals, short-form video, reels, or illustrative storytelling for social or community platforms.

• Community Engagement (20%) - Strong interpersonal and communication skills, both online and offline.

You'll Thrive if You

Have experience working with a non-profit, grassroots initiative, or programs focused on women.

Are comfortable working with little structure and excited to create your own.

Love styling, fashion history, thrifting, and expressive fashion.

Feel comfortable creating digital content independently.

Get energy from leading small group sessions and connecting 1-on-1.

Are organized and proactive, especially when it comes to logistics and event planning.

Want your work to feel authentic, expressive, and aligned with your values.

What's in it for You

The chance to shape and lead a new program from the ground up

Creative freedom to choose the program's theme and direction

A role that blends styling, community, and storytelling

Being part of the beginning of a meaningful, people-first initiative

A growth path into future leadership roles within the organization

This is a non-profit organisation. Compensation for this role will be $15/hr - $17/hr.

For budget reasons, preference will be given to residents in the Vaughan area or in close proximity.