In an exclusive conversation with Syeda Beenish, Co-Founder Editor, NewzOnClick, Diya Girish, Sales Head & Director – India and SAARC at Milestone Systems, reflects on her two-decade career spanning technology, leadership, and enterprise sales. From her early beginnings as a computer science graduate to leading mission-critical public safety solutions in a fast-changing technology ecosystem, Diya shares her experiences of navigating industry shifts, breaking gender stereotypes, and building people-centric teams. An avid traveller by hobby and known for her ability to find clarity in chaos, her insights underscore the value of curiosity, lifelong learning, and purpose-led leadership in creating a sustainable and impactful career in technology. Below are the excerpts…
1. What initially inspired you to pursue a career in the IT industry, and how did you take your first steps into the tech world?
I graduated as a Computer science engineer back when the dialup modem sounded like it was fighting for its life. I very quickly realised I loved talking about tech more than actually coding it.
I was fascinated by how technology could solve real business problems and transform entire industries… Some people love fiction; I apparently love “return on investment”.
That curiosity pulled me into tech sales, where I became the translator between “complex tech” and “why this matter for your business.” One curiosity-led step after another eventually turned into leadership… much like how you open one tab and suddenly have 26.
2. What were some of the biggest challenges you faced as a woman in IT, and how did you overcome them?
When I started out, women in tech sales were… let’s just say, not a common sight. Interviews were rarely about capability. Instead, I got questions like “Can you travel?” or “Will you be able to handle pressure?” I used to wonder if anyone asked my male colleagues whether they could handle pressure or pack a suitcase!
My strategy was simple: deliver results so consistently that stereotypes didn’t stand a chance.
Fast forward 20 years: Now, the challenge is different – suddenly every second job is a “diversity role.” While well-intentioned, it can feel limiting to women who want to be recognised for talent, not tokenism. And yes, the classic-being seen as a leader, not a “female leader.” I’ve learned that if you lead with clarity and competence long enough, the label quietly retires.
3. How has your role — and the industry — evolved since you started, and what shaped your professional growth the most?
My journey has taken me from an entry-level sales professional to leading an organisation at a country level, and somewhere along the way the entire industry reinvented itself — several times!
We went from on-premises to cloud to AI to “AI but with more enthusiasm”. Every shift demanded new skills, new thinking, and sometimes the humility to say, “Alright, time to unlearn that.” The industry reinvented itself so often that staying relevant basically meant becoming a full-time learner. The moment you think you’ve mastered something, someone releases version 2.0.
Growing professionally came from staying curious and staying humble – two things tech forces you into anyway. And doing all this during India’s massive tech transformation? That’s been the real privilege. It’s like being part of a national startup.
4. What has been your most rewarding achievement so far, and how do you aim to create impact?
Honestly, my proudest achievement isn’t a job title or a big deal- it’s the relationships. Customers, partners, teams. I have somehow managed to create groups that feel less like departments and more like slightly chaotic but loyal families.
At Milestone Systems, our work in public safety gives real purpose to what we do. It feels good to know the tech you talk about might help keep someone safe.
If I inspire people at all, I hope it’s by showing that tech leadership isn’t only about numbers or innovation, it’s about people, purpose, and leaving teams better than you found them.
5. What advice would you give to young women aspiring to build a career in tech, especially in male-dominated fields?
First: keep your confidence close — like your phone, but without the endless notifications. You were hired because of your talent and potential. Believe in that and keep building on it.
Second: choose intentionally. Work toward a stage in your career where you choose the technology you want to work on, the teams you want to be part of, and the leaders you want to learn from. And finally yes, some fields are male dominated, but many of my strongest allies, mentors, and supporters have been men who genuinely believe in creating equal space. Bias exists everywhere but so does fairness. Courage, and competence don’t belong to any one gender, so back yourself, choose your tribe wisely.
