Finding Your Voice: Anna May Taylor on Leadership, Community, and Grit

Anna May Taylor is the Director of Service Delivery at Vintri Technologies, where she leads through connection rather than control — building opportunities, amplifying stories, and helping others find their voice. Her career spans global collaborations across the Philippines, India, Romania, Canada, and the U.S., experiences that reshaped her view of technology from mere systems and code to a force for human connection.

From once being the quietest voice in the room to mentoring others to lead with confidence, Anna’s journey is one of courage, community, and continuous growth. When she’s not empowering teams, she’s training for ultra-marathons — living proof that endurance, discipline, and curiosity are universal tools for both life and leadership.

The moment that changed everything

Anna’s “this is it” moment didn’t come from a lightning-bolt epiphany — it arrived through collaboration. Working in Customer Success at a very large tech company, she found herself partnering with colleagues across the Philippines, India, Romania, Canada, and the U.S. Seeing teams with different cultures and strengths come together to solve real problems shifted her idea of tech from code and products to connection and collective muscle.

That cross-border teamwork made her realize tech is a multiplier: when diverse strengths meet, the results are far greater than the sum of the parts.

Early setbacks that became lessons

Like many early in their careers, Anna remembers being the quiet person in the room — convinced she didn’t have the right experience to speak up. She’d hold back when she should’ve pushed, and that silence taught her something crucial: curiosity matters — and genuine curiosity, asked from a place of wanting to learn and contribute, grows confidence.

Anna’s path from reticence to voice is a reminder that confidence is built, not found. Asking questions with sincerity became one of her most reliable tools for impact.

Mentors, moments, and community energy

Anna describes support not as a single mentor or program but as “pockets” of encouragement — fleeting conversations, seasonal friendships, and lasting connections that arrive when energy flows the right way. Communities like CITI, she says, are places where those pockets collect and multiply.

CITI gave her access to stories and perspectives that acted as signals — guiding what to learn next and who to reach out to. For Anna, community isn’t just networking; it’s a practice of listening and returning energy.

What’s keeping Anna busy (and excited)

Outside of work, Anna channels the same discipline and curiosity into extreme endurance: she’s training for an ultra running race in Argentina later this year. The project is equal parts physical grit and cultural immersion — she’s even learning Spanish so she can fully engage with the experience.

The race is also a study in adaptability: preparing in our winter for Argentina’s summer, coping with different elevations and climates, and testing how the body and mind respond to change. It’s a practical metaphor for her professional life — endurance, preparation, and the willingness to learn.

The next 3–5 years, What's on the horizon?

When asked where she sees her tech journey going, Anna uses a simple but potent phrase: “boots on the ground.” It’s less a fixed plan and more a promise — to stay close to the work, the people, and the real-world problems that need solving. She wants to remain engaged in projects that demand presence and practical impact, not just from a distance but in the trenches with teams and communities.

To connect with Anna and other professionals like her, Join the CITI Community here: https://www.careerintech.ca/