The RSPA W2W Leader of the Year award honors a trailblazing woman in retail technology annually at RetailNOW. The 2024 RSPA W2W Leader of the Year was awarded to Allie Haskell of ISV CBS NorthStar.
Haskell has spent the last 13 years in the retail and hospitality IT channel building multiple departments. Outside of work, she stays busy with her two energetic kids. A dedicated RSPA member, she represents NorthStar as a Board Member, Co-Chair of the NextGen Community, W2W Advisory Group Member, and an RSPA NextGen Rising Star.
We asked Haskell about her journey and growth opportunities for women in today’s retail IT channel:
1. What inspired you to enter the retail IT industry?
I didn’t wake up one daydreaming of retail IT. I’ve always loved making people happy, and restaurants are where that magic happens. During college, I started serving tables, left to chase my soccer dreams, then came back home needing a job. I landed here, and somewhere between the chaos of tech calls and the joy of helping restaurants run smoother, I fell in love with it. It ties together everything I’ve done – teamwork, problem-solving, and creating amazing guest experiences. Now, I can’t imagine doing anything else.
2. What significant advancements or changes have you witnessed in the industry or within the association?
This industry has gone from clunky hardware and manual processes to sleek, cloud-based, AI-driven platforms. But here’s the kicker: fancy tech doesn’t mean much if it doesn’t solve real problems. The biggest shift I’ve seen is more companies finally getting that. Tech isn’t the hero; it’s the tool. The hero is the operator who uses it to create unforgettable guest experiences.
3. What drives you to keep innovating and pushing boundaries in your career?
I hate the phrase, “This is how we’ve always done it.” Innovation is about staying uncomfortable, asking weird questions, and refusing to settle for “good enough.” Plus, there’s nothing better than watching a client go from frustrated to, “Holy crap, this works!“ Honestly, my kids help me here, too. They ask the wildest, most unfiltered questions – like, ‘Why can’t we just have flying pizza?’ – and it reminds me to zoom out and think bigger. If we only solve today’s problems, we’re missing the magic of what’s possible tomorrow.
4. Can you share a defining moment in your career that influenced your leadership path?
A pivotal moment for me was stepping into a leadership role at CBS NorthStar during COVID – a time when everything felt uncertain. I quickly realized that success wasn’t just about delivering great products; it was about empowering our team, listening to our clients, and staying adaptable. That experience taught me that real leadership means creating environments where others can thrive, even in the midst of chaos.
5. What challenges have you encountered as a leader, and how have you overcome them?
Early on, I thought good leadership meant knowing everything. I’ve learned it’s actually about knowing when to ask for help, when to trust your team, and when to admit, “Yeah, I don’t know – but let’s figure it out together.” Letting go of that pressure and embracing the unknown has made me a better leader, a better teammate, and honestly, a better human. The work gets easier when you stop pretending and start collaborating.
6. How do you mentor and uplift other women in the industry?
Honestly, I don’t even really see myself as a mentor most days. I still wrestle with imposter syndrome – like, who am I to give advice when I’m still figuring it out myself? But maybe that’s exactly why I share so openly.
I talk about the wins, sure, but I also share the mistakes and those “What the hell am I doing?” moments. We don’t need more perfectly packaged advice; we need to know that we’re not alone in feeling like we’re making it up as we go.
I tell women to take up space – be loud, bold, and true to themselves. We’re just people at the end of the day, just like our male coworkers who don’t seem to hesitate before speaking up. So why should we? The industry needs more of us – real, unfiltered, and unapologetically present.
7. What impact do you hope to leave on the industry and future women leaders?
I want to leave behind a trail of women (and men) who show up unapologetically – big ideas, bold moves, and zero second-guessing. I want women to stop overthinking whether they belong in the room and start owning the damn room.
The goal? Less apologizing, more action. Less, “Am I qualified?” and more, “Watch me do it.”
If even a handful of people walk away from something I said or did and feel empowered to trust their gut, push boundaries, and go after what they want – then I’ll know I left my mark. The industry needs more women who are done playing small and ready to take up space. Let’s be those women.
8. Your LinkedIn blog series “Between Two Terminals” is a great example of bold content sharing. What impact do you think bold content sharing has on others, and how can it encourage more people to share their own stories?
Bold content sharing isn’t just about making noise. It’s about making an impact. When we put real, unfiltered conversations out there, it gives others permission to do the same. “Between Two Terminals” isn’t just about stirring the pot; it’s about getting people to think, challenge norms, and start conversations that actually matter in this industry.
The impact? It builds trust, drives engagement, and creates a space where people feel seen and heard. When we stop sugarcoating and start being real, more people feel empowered to share their own stories. Whether that’s about industry challenges, big wins, or the messy middle. Bold content sparks bold conversations, and that’s how we move things forward.
9. How do you see the role of women evolving in this industry, and what steps can be taken to further support them?
I’m just excited to see more women showing up – and not just physically being in the room, but showing up as their full, authentic selves. We’re seeing more women stepping into leadership, speaking at conferences, and driving innovation without trying to fit into some outdated mold. The industry is finally recognizing that diverse perspectives lead to better solutions.
Keep showing up. Keep supporting each other. And let’s stop waiting for permission to take up space. The more we show up, the more the industry will shift.
10. If you could offer one key lesson to the next generation of women in this field, what would it be?
Stop waiting for the stars to align – just go for it. Perfection is a myth, and confidence doesn’t come from having it all figured out. It comes from taking the shot, owning your voice, and showing up exactly as you are. Crack the joke. Wear the bold lipstick. Ask the “dumb” question – spoiler: it’s probably the smartest one in the room. Don’t shrink yourself to fit some outdated definition of professional. The industry doesn’t need more perfectly polished personas – it needs more bold, unapologetic women who show up, speak up, and shake things up. Be that woman.
RSPA and its members continue to collaborate and create opportunities. A prime example is best practice sharing that takes place in the RSPA Community meetings. The RSPA W2W Community meets to provide a support network and resources for women as they enter and continue to advance in the retail technology industry. If you would like to get involved in the W2W Community, please email RSPA Member Services Team at Membership@GoRSPA.org.
The RSPA W2W Leader of the Year was created to recognize a woman in the Retail Technology Industry, who is determined to reshape the industry and create a smarter and more inclusive future. This honor recognizes a woman who has demonstrated key characteristics of a pioneer paving the way in the Retail Technology Industry. The RSPA is accepting nominations for the 2025 RSPA’s Leader of the Year Award. To nominate, please fill out the form on the W2W Community page.
