Timestamps:

00:44 From HR to Sales: The Initial Leap

02:53 Overcoming Early Challenges in Sales

05:04 Gender Dynamics in the New Business Team

07:28 The Drive to Leadership

08:59 Leading Diversity Initiatives at Google

11:42 Addressing Challenges in Scaling Organisations

18:41 The Importance of Sponsorship and Retention

20:51 Creating an Environment for Progression

About Emma Cahalane:

Emma Cahalane is a high-performance sales leader with a proven track record in scaling businesses. Starting her career at Google in HR, Emma quickly transitioned to New Business Sales, eventually managing a $100M business. She has since spearheaded sales teams at fast-growing startups such as Sonder, Pym, and DoorDash, where she currently oversees a $1B business and a team of 70.

From HR to Sales: The Initial Leap

Emma's transition into sales wasn't an overnight success. She spent three years at Google in the HR department before deciding to make the switch. Despite her curiosity and desire to work with small businesses, Emma faced multiple rejections when she applied for sales roles within the company. She lacked sales experience and struggled with the interview process, applying for four or five roles over a year without success.

Determined to succeed, Emma applied for a challenging position in the new business sales team—a team that others avoided. Her perseverance paid off when the manager took a chance on her, making her the first internal transfer globally into that team. This role provided Emma with a solid foundation in sales, particularly through cold calling and selling Google products in the UK and Ireland markets. Despite initial challenges, this experience was crucial in shaping her sales career.

Overcoming Early Challenges in Sales

The first three to six months in the new business sales team were particularly tough for Emma. The competitive nature of the team, coupled with being one of only two females in a group of 20, created a unique and challenging environment. Emma faced setbacks, including receiving incorrect information from a buddy assigned to help her, which was an unusual and isolated experience within Google.

However, these challenges taught Emma the importance of self-reliance and building trustworthy relationships. She persevered by taking ownership of her learning and identifying reliable sources of information within the team. Emma's resilience and determination to prove herself and succeed were key factors in her early sales career.

Navigating Gender Dynamics in Sales

Emma's experience in the new business sales team highlighted the stark contrast in gender dynamics compared to her previous HR role. Being one of the few females in a predominantly male team was challenging, but Emma viewed it as a competitive edge. Her unique perspective allowed her to connect with customers in a different way, turning what could have been a disadvantage into an opportunity.

Emma's determination to succeed in a male-dominated environment was driven by a desire to prove herself and make the most of the opportunity given to her by her manager. Her perseverance and ability to see challenges as opportunities played a significant role in her success.

The Drive to Leadership

Emma's journey into leadership was driven by her passion for coaching and developing others. She observed many poor managers throughout her career, which inspired her to become a leader for the right reasons. Emma's natural interest in mentorship and her desire to make a positive impact on people's careers motivated her to pursue leadership roles.

Her first leadership position came at Google in the Australia office, where she was given opportunities through management development programs. Emma's approach to leadership was shaped by her experiences with ineffective managers, and she was determined to treat her team with respect, develop their skills, and create a positive work environment.

Leading Diversity Initiatives at Google

Emma's involvement in Google's diversity programs began when she joined Women at Google in 2016. Co-leading the resource group, Emma aimed to revitalise the program, which had been facing challenges in making significant changes to female representation in leadership positions. She and her co-leader worked to bring in new people, involve more leadership, and create a mission focused on building community and fostering relationships both within and outside Google.

One of their key initiatives was creating Connected Women, an organisation that brought together women from major tech companies in Australia for networking events and speakers. This initiative helped build a strong community and created opportunities for women to move between companies, addressing the industry's reliance on networks for recruitment.

Addressing Challenges in Scaling Organisations

Emma's experience at Sonder, where she joined as the General Manager for Vancouver, highlighted the challenges of scaling a rapidly growing company. During the interview process, Emma noticed a lack of diversity among her interviewers, which raised red flags. She took it upon herself to address these issues once she joined the company.

Emma worked closely with the recruitment team to improve diversity in hiring practices. They focused on creating inclusive job descriptions, building a diverse pipeline of candidates, and reaching out proactively to underrepresented groups. These efforts led to significant improvements, including the hiring of five female general managers within six months.

The Importance of Sponsorship and Retention

Emma emphasised that developing and retaining female talent is even more critical than hiring. She advocated for the importance of sponsorship—having influential people within the organisation who can champion your career. Emma's approach included creating structured programs that paired employees with senior leaders to build these crucial relationships.

Additionally, Emma highlighted the need for flexible work arrangements, such as part-time opportunities and job sharing, to retain diverse talent. Companies must demonstrate their commitment to diversity by valuing and supporting these roles, even during economic downturns.

Creating Progression Opportunities

Emma advised individuals to actively build their internal and external networks to progress in their careers. She shared her experience of having regular coffee meetings with people from different teams to explore opportunities and learn about the market. Building relationships and being proactive in seeking opportunities are essential for career progression.

Emma also stressed the importance of being explicit about career goals with managers, consistently demonstrating your achievements, and ensuring your contributions are recognized. This proactive approach can help individuals navigate organisational politics and achieve their career aspirations.

Conclusion

Emma Cahalane's journey from HR to sales leadership is a testament to her resilience, determination, and passion for making a positive impact. Her experiences highlight the importance of perseverance, building trustworthy relationships, and advocating for diversity and inclusion. Emma's story offers valuable insights for anyone looking to transition careers, overcome challenges, and succeed in leadership roles. By focusing on personal development, building networks, and creating inclusive environments, individuals and organisations can achieve remarkable growth and success.