Building with Purpose
Al-Karim Khimji knows how to run complex operations. He watched a hotel rise from a dirt lot to a successful business. Then he built a property tech company that serves landlords across North America. At every step, he focused on solving real problems with empathy and precision.Born and raised in Calgary, Al-Karim began his career in the hospitality industry, managing all aspects of hotel development. He handled franchising, financing, construction, and operations. Later, he worked in private equity in the Middle East before returning to Calgary and joining McKinsey & Company. Even while at McKinsey, he built his own rental portfolio.That project revealed a market gap. Large property owners had advanced software. Small landlords got by with basic tools. But mid-sized landlords had nothing suitable. "There are great tools for 1 to 10 units, and for 20,000-plus units," he said. "But for those in between? Not so much."That insight led him to co-found Propra with Craig, a former tech leader at SkipTheDishes. They built tools tailored for landlords managing 25 to 2,500 doors—a massive but overlooked market.Selling to a Market That Doesn't Want to Be Sold To
Coding and fundraising were not the toughest parts of building Propra. Selling was. Their ideal customers didn’t see themselves as buyers."A lot of them are small business owners," Al-Karim explained. "They might be doctors, lawyers, or families running a portfolio. They don’t think of themselves as professional property managers."They often hesitated to change what worked. Many managed hundreds of units using spreadsheets, email, and QuickBooks. "If it's not broken, why fix it?" That mindset made selling difficult."You can call someone 100 times," Al-Karim said, "but if they don't want it, they don't want it.""Our biggest competitor isn't another software platform. It's inertia. It's the belief that change isn't worth the effort."That realization changed their strategy. Instead of pitching harder, they started listening better.Stop Pitching, Start Listening
Early in his McKinsey career, a mentor gave Al-Karim simple advice: Listen. Don’t assume. Understand before you respond. That advice shaped Propra's sales approach."We get to 'Hell Yes' by uncovering the problem, not pushing a solution," he said. "Sometimes customers show up and already know what they need. But most of the time, we need to ask questions and listen."That shift allowed Propra to meet customers where they were. Some searched for new tools. Others felt content. Still others discovered problems through conversation.One trade show visitor circled their booth several times. Al-Karim paused a chat to greet him. The man said, "I need this now.""When someone says that, you know the timing is right. You just have to get out of the way and help them buy."But readiness isn’t everything. Fit matters. "Sometimes we tell them, 'Keep using Excel. It works for you.' That honesty builds trust."That trust pays off. "We’ve had people say no to using Propra but then refer someone else. That only happens when you build real relationships."Build for Fit, Not for Force
How does Propra get customers to say "Hell Yes"?They follow four principles:- Start with Fit: They target landlords managing 25 to 2,500 units. These landlords are too big for spreadsheets but too small for legacy software.
- Listen Deeply: Every call and meeting becomes a discovery session. They ask what slows the customer down, what works, and what needs to change.
- Simplify the Solution: Customers want results, not complexity. Propra automates tasks and combines tools into one platform.
- Earn Trust Continuously: Every interaction builds or breaks trust. They stay honest, helpful, and consistent—even if that means walking away.
Three Takeaways About Getting to Hell Yes!
What does it take to hear "Hell Yes" from a customer? Here are three lessons from Al-Karim Khimji:1. Release Your Agenda
Don’t go into calls trying to sell. Go in to understand. Ask questions:- What’s slowing you down?
- What’s already working?
- What would make your life easier?
2. Be Politely Persistent
Follow up with purpose. Share helpful content. Ask for one referral. Don’t spam. Always add value.As Al-Karim puts it: "Be politely annoying. Not spammy—just present.""A lot of our deals close not because we pushed harder, but because we stayed helpful."3. Let Listening Lead the Way
You don’t pitch your way to "Hell Yes." You listen your way there.Prepare your questions. Practice them. Stay curious. The more you understand the customer’s world, the more clearly your solution fits."If you're not adding value in the first conversation, you've lost the next one."Bonus Insight
Personas often mislead. They reflect who you hope to sell to, not who actually buys. Al-Karim suggests reading job descriptions instead. "If you want to sell to a VP of Operations, read their job description. That’s your real persona."The Hell Yes Mindset
Getting to "Hell Yes" isn’t about tactics. It’s a mindset:- Meet people where they are
- Be honest about fit
- Build long-term trust
Ready to discover your 'Hell Yes' moment?
👉 Visit www.propra.tech to see how Propra makes property management easier.👉 Or connect with Al-Karim Khimji on LinkedIn to keep learning from his journey.Let us know what your version of "Hell Yes" looks like.Our mission is to simplify the homeowners & home builders customer experience. Let Iris do the work.
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