How Chitra Singh is helping women break the glass ceiling in sales

When HerStory spoke with Saleswomentoring Founder Chitra Singh in 2022, she was focusing on increasing the talent pipeline of women in sales.

Three years and many challenges later, Singh is still going strong. In her latest interview with HerStory, Singh spoke about building Saleswomentoring— a platform committed to advancing women's leadership in sales .

"Last year, I had six major corporations partnering with us. Three are returning this year alongside several new clients," Singh reveals. 

Saleswomentoring has also introduced certification programmes for women in sales at every level, one-on-one coaching for senior women leaders, a program for founders and startup owners.

What began with barely 200 members in 2020 has grown into a 2,000-strong army of sales professionals using the Saleswomentoring platform to advance their goals.

Closing the sales gap

According to a LinkedIn study, women constitute 19% of the sales workforce in India with only 13% holding sales leadership positions.

With Saleswomentoring, Singh is working to break the very glass ceiling she spent nearly 30 years pushing against.

“I was always the only female in the room,” Singh recalls her early days at Johnson & Johnson as the company’s lone female medical representative in India. “I thoroughly enjoyed it because I felt that selling is a service, and you are helping somebody achieve something but it’s also a profession women avoid,” she adds.

After completing her MBA from NMIMS, Mumbai, Singh joined AF Ferguson and then moved to banking in 1995. She served in leadership roles at Times Bank, ICICI, Kotak, HDFC Bank and headed the launch team at Jana Small Bank, her last role in sales.

"At each stage, I was the only woman sales leader—branch manager, regional head, national head—always the only woman. I always felt being a woman in sales was an advantage. Sometimes I was a source of amusement, other times, entertainment but I was always a rarity  to something unique,” she explains.

By 2019 Singh had conquered every challenge the banking world had thrown her way. But something was missing. "Everyone complained about the lack of women in sales, but nobody was doing anything about it," she says.

The journey

A solo trip to witness the Northern Lights brought in a much-needed moment of clarity. She decided to combine her passion for sales and help women make decisions independently and negotiate their value at work in life. 

Singh's case for change is backed by data. She says despite forming 35-40% of entry-level sales forces, women in Indian sales leadership remain low. Women achieve sales quotas at rates 8% higher than men, teams led by women show 3% higher quota achievement rates, the average value of deals closed by women is $5,000 higher and yet, women in sales are paid 21% less than their male counterparts.

The industries presenting the steepest climbs include where women are dismissed as "pesky loan callers," and tech sales, where gender bias compounds with STEM stereotypes to create impossible barriers.

Singh started Saleswomentoring in 2020 as a free community before evolving into what she describes as “a movement to change the narrative around women in sales.”

With the help of 10 mentors, Saleswomentoring aims to power sales leadership through transformational learning programmes, customised hiring, expert mentorship and a supportive community to help women to advance and thrive in sales.

"Women are community-led. They don't just want advice—they want belonging. They want to see living proof that success in sales isn't just possible; it's achievable,” she asserts.

An ecosystem for women in sales

Saleswomentoring aims to build a complete sales ecosystem for women. Its foundation rests on the community of sisterhood. While free entry-level access gives women a taste of what’s possible, premium and VIP memberships unlock direct mentorship from the mentorship team. Every month, all members can attend two virtual workshops that work on all-round transformation.

After participating in the Stanford Seed Spark Program, Singh decided to pivot to a B2B model.

"We don't do workshops, we create journeys—three to four-month transformations that reshape how organisations see women in sales." It works on a modular design like “Lego blocks, companies can build their programme piece by piece.” It also aims to target a mindset change, integrate life skills and lead to measurable outcomes like higher retention, increased performance and improved diversity.

Challenges of women in sales

Singh highlights the four challenges women in sales often face—marriage, mobility, maternity, and she adds mothers-in-law to the mix because she believes that they deter women from pursuing a career in sales.

But she counters with her own—three Ms that serve as antidotes: "Your mother, your manager, and your mentor." She pauses before adding with a smile, "And if you can find a sponsor, even better."

"We've been conditioned to diminish, devalue, and deprioritise ourselves," We call it sacrifice or accommodation, but let's call it what it really is—systematic devaluation,” Singh observes.

"Each woman who continues in sales instead of quitting is my victory," Singh declares.

She wants to start a sales university in the future and also expand Saleswomentoring to include more alliances and partnership and also integrate AI into the mentoring process.

Importantly, she wants to encourage women who have dropped out of the salesforce to return. 

“They require constant mentorship, structured guidance and corporate sponsorship and I hope to help them rebuild their careers,” she says.