In Conversation with Heather Flynn

Tell us about your background:

I am an inspiring, values-driven leader and coach with a proven track record of year-over-year success in building a strong, supportive culture that drives impactful results. With over 22 years of experience in Talent Acquisition leadership roles working with both smaller start ups and large global brands. My most recent experience was as the SVP Talent Acquisition at Aritzia. Throughout my career I have demonstrated a unique ability to motivate both teams and individuals, fostering environments that empower employees to reach their full potential while delivering exceptional business outcomes.

My background spans the tech industry and retail. Throughout my career, I have been an influential, consultative, and results-driven leader, consistently making a positive impact on corporate success. I am deeply committed to developing and implementing strategies that not only meet but exceed organizational goals, particularly in the areas of talent acquisition, team development, and organizational growth. My expertise is in strategic planning and my ability to align people with business objectives to drive sustainable results for companies across various industries.

What do you wish you’d known when you started out?

Looking back on the start of my career, one thing I wish I had known is that success isn’t always a straight path up. Sometimes, you need to move sideways to ultimately move forward. The key is to embrace those detours, as they often offer valuable experiences and new perspectives. Another important lesson is to identify strong leaders within your company early on and seek out opportunities to learn from them—whether through an official mentorship or informal guidance. Having advocates throughout the organization can make a significant difference in your career growth, providing support, insight, and opportunities that propel you forward.

Best career advice you've ever received?

"Never let a good crisis go to waste." This advice has always resonated with me because it serves as a reminder that every challenge is an opportunity for growth and learning. In the midst of a crisis, it’s crucial to stay focused on finding solutions, gaining insights, and ensuring that the same issues don’t arise again in the future. Remaining calm and strategic during difficult situations not only helps navigate through them effectively but also instills confidence in your team, demonstrating your ability to lead with clarity and resilience.

What leadership qualities are important to you?

Great leadership is the most important thing to me at this point in my career. An authentic, people-first, values-driven, embodying emotional intelligence, empathy, and integrity, fostering a culture of trust, collaboration, and accountability. Ability to inspire and motivate teams by actively listening, providing mentorship, and aligning individual goals with a clear organizational vision. Being able to prioritize inclusivity, adaptability, and open communication, ensuring that everyone feels valued and empowered to contribute.

What has been the biggest challenge in your career so far?

The last five years have presented one of the greatest challenges of my career in Talent Acquisition. I have had to shift my perspective from the expectation of long-term tenure with each organization to a more strategic, one-year-at-a-time focus. This shift required balancing optimism about a company’s potential for growth and investment in Talent Acquisition with the understanding that not all organizations prioritize the same level of commitment to this function. While hoping for continued investment and alignment with my goals, I have remained agile, preparing for the reality that, at times, the company’s priorities may not align with the evolution of Talent Acquisition. This experience has strengthened my ability to adapt quickly and to navigate uncertainty while maintaining a focus on achieving impactful results.

How do you define success in your career, and how has that definition evolved over time?

Throughout my career, I’ve come to define success not by personal career milestones, but by the impact I’ve had on the individuals I’ve had the privilege of leading. Early on, I was more focused on traditional markers of success, such as career trajectory and titles. However, over time, I’ve realized that the true measure of my success lies in the lasting influence I’ve had on others. The fact that many of those who have worked with me consider me the best leader they’ve ever had, and have followed me to new opportunities, is a testament to the positive and meaningful relationships I’ve built. This level of trust and loyalty from my team reflects my commitment to developing and empowering individuals, and it is this legacy of leadership that I am most proud of.

How has networking contributed to your professional growth and success?

Networking is an essential aspect of career growth, particularly in recruitment, where it is deeply ingrained in our daily practices. For me, networking has been a cornerstone of success, with nearly every opportunity in my career stemming from referrals rather than traditional applications. I strongly advocate for the power of networking within organizations, emphasizing to leadership teams that fostering connections across the industry is not just the responsibility of the recruitment team, but of everyone. It’s critical that we all stay connected with top talent and remain aware of the best practices and innovations happening at leading companies. Building and maintaining a strong professional network empowers us to stay ahead of industry trends and ensures we have access to the right people and opportunities when they arise.

What are your top networking tips for building strong connections in your industry?

When it comes to networking, authenticity is key. Approach it like a bank—before you can make a withdrawal, you need to make deposits. These "deposits" are the value you bring to your network, whether through support, insights, or genuine connections, before expecting anything in return. Another effective strategy is setting micro goals for yourself at events. Instead of trying to meet everyone, focus on meeting just a few key individuals—like setting a goal to connect with two people. This allows for more meaningful conversations and stronger relationships. Additionally, take the time to research the event’s speakers or leaders, as they are often the most well-connected individuals in the room. Making an effort to connect with them can open doors to valuable opportunities and expand your network significantly.

LinkedIn: https://www.linkedin.com/in/heather-cross-flynn-535528/

Instagram: @heathercrossflynn