Women in Sales on confidence, challenges & career wins

Working in sales as a woman comes with its own set of challenges – some obvious, others less so. From the pressure to prove your expertise to navigating leadership roles and unspoken biases, there’s a lot that doesn’t show up in job descriptions.

At Haiilo, we asked two of our leaders, Mariam Tahan and Sarina Spector, to share what it’s really like. No buzzwords, no gloss – just honest insights on confidence, career growth, and rewriting outdated ideas about who thrives in sales.

1. What advice would you give to young women aspiring to break into your industry?

Mariam: You don’t need permission to take up space, so don’t wait! Both Sales and SaaS can sometimes feel fast-paced and competitive, but confidence and resilience will pay off! 

It’s really important to learn as much as possible about the business, build relationships and definitely, don’t be afraid of advocating for yourself – whether that’s in negotiations, promotions, or leadership opportunities. Most importantly, find people and mentors who will inspire and challenge you!

Sarina: The first thing is to be mindful of your mindset. While it’s true that certain industries are male-dominated, focusing too much on that can create a feeling of being an outsider. If you internalize that idea, you may start behaving differently, feeling like you need to change yourself to fit in. 

Instead, recognize your own value as an individual, regardless of gender. If you dwell on the idea that you don’t belong, you may subconsciously manifest that belief in how you behave and perceive situations. I personally didn’t even realize for months that I was the only woman in the room at my workplace because no one made me feel different. Had I been overly focused on it, I might have behaved differently.

2. What’s one unexpected challenge you’ve faced along the way?

Mariam: The transition from being an individual contributor to both an individual contributor and leading individuals was definitely challenging. In sales, you’re used to driving your own success, but when you start to lead people, it is about empowering others. Learning how to coach, inspire, and navigate different personalities while keeping performance high is one hell of a learning curve – but one that ultimately helped me grow a lot.

Sarina: Appearance plays a bigger role in a woman’s career than it does for men. Things like work attire require more thought because people perceive women differently based on what they wear and how they present themselves. It’s not always a disadvantage – it can be an opportunity to use appearance as a confidence booster – but it is an added consideration that men don’t face as much.

3. If you could go back in time, what’s one thing you’d tell your younger self about working in this field?

Mariam: Trust yourself more. You don’t need to have all the answers to take on big challenges. In account management, things are constantly evolving, and adaptability is more valuable than perfection. I’d tell myself to take more risks, speak up sooner, and not overthink every decision, because growth comes from stepping outside of your comfort zone.

Sarina: Honestly, I wouldn’t change much. I’d tell myself to keep my confidence. I’ve always been a fairly confident person, and I think that’s important. For those who aren’t naturally confident, I’d encourage a “fake it till you make it” approach – act like you know what you’re doing, and then do the work to fill in the gaps. Don’t sell yourself short.

I also learned early on how to build resilience. I worked in restaurants as a teenager, where you had to deal with inappropriate comments constantly. That environment toughened me up and made entering a male-dominated field feel like less of a challenge. However, if I could go back, I’d tell my younger self to not just endure toxic behavior but to understand that it’s not acceptable and to advocate for myself.

4. What’s one stereotype or misconception about women in your industry that you’d love to break?

Mariam: That women aren’t as aggressive or strategic in sales and leadership. There’s this outdated idea that success in sales requires a cutthroat approach, but in reality, relationship-building, emotional intelligence, and long-term vision drive real impact. Women bring unique strengths to the table, and it’s time we shift the narrative to recognise and celebrate that.

Sarina: Sales is full of stereotypes. One of the biggest misconceptions is that salespeople are pushy, manipulative, or scheming. That’s already inaccurate, but when you add gender into the mix, it gets more complicated. Those stereotypes often apply more to men, which seems like a positive for women in sales. However, if those traits are seen as what makes a “good salesperson,” does that mean women are seen as less effective?

Rather than focusing on whether women fit into these stereotypes, I think we need to challenge the underlying assumption that those qualities make someone a good salesperson in the first place. In reality, women actually outperform men on quota attainment, according to data. The industry is shifting, but we still have work to do in reshaping the perception of what makes someone successful in sales.

5. What’s a moment in your career that made you feel especially proud or validated your efforts?

Mariam: Closing my biggest Advocacy deal of my time at Haiilo and winning the ‘Will to Win’ award at Haiilo was a huge moment for me. It wasn’t just about performance – it was recognition for resilience, leadership, and the impact I had on the team.

Sarina: One stereotype about women is that we prioritize caring for others – and ironically, that’s where my proudest moments come from. Even though I see myself as a very self-driven person, what makes me most proud at work is helping my team succeed. That’s why I love leadership and management – my team’s wins are my wins. Getting people promoted, helping them get raises, and supporting them in achieving their goals is what makes me feel like I’ve truly added value.